Complete Organic Sheet Merged by Techy Rathore

(Organic Chemistry) Classification and Nomenclature
EXERCISE - I
Q.1 How many 𝟏∘ carbon atom will be present in a simplest open chain hydrocarbon having two 𝟑∘
and one 𝟐∘ carbon atom?
(A) 3 (B) 4 (C) 5 (D) 6
Q.2 Alicyclic compounds are
(A) Aromatic compounds (B) Aliphatic cyclic compounds
(C) Heterocyclic compounds (D) None of the above
Q.3 How many 𝟏∘ , 𝟐∘ , 𝟑∘ 𝐂 atoms does 𝟏, 𝟑, 𝟓-Trimethyl cyclohexane have?
(A) 𝟑, 𝟔, 𝟎 (B) 𝟑, 𝟒, 𝟐 (C) 𝟎, 𝟑, 𝟔 (D) 𝟑, 𝟑, 𝟑
Q.4 The compound which has one isopropyl group is:
(A) 2,2,3,3-Tetramethyl pentane (B) 2,2-Dimethyl pentane
(C) 2,2,3-Trimethyl pentane (D) 2-Methyl pentane
Q.5 Which of the following is the first member of ester homologous series?
(A) Ethyl ethanoate (B) Methyl ethanoate
(C) Methyl methanoate (D) Ethyl methanoate
Q.6 A group closely related compounds which can be expressed by a general formula & in which two
conscutive members differ by 14 in their molecular masses is called
(A) a heterogeneous series (B) a homologous series
(C) a homogeneous series (D) a electrochemical series
Q.7
Number of secondary carbon atoms present in the above compounds are respectively:
(A) 𝟔, 𝟒, 𝟓 (B) 4,5,6 (C) 𝟓, 𝟒, 𝟔 (D) 𝟔, 𝟐, 𝟏
Q.8 The molecular formula of the first member of the family of alkenynes and its name is given by
the set
(A) 𝐂𝟑 𝐇𝟔 , Alkene (B) 𝐂𝟓 𝐇𝟔 , Pent-1-en-3-yne
(C) 𝐂𝟔 𝐇𝟖 , Hex-1-en-5-yne (D) 𝐂𝟒 𝐇𝟒 , Butenyne
Q.9 Which of the following is a heterocyclic compound
(A) (B)
(C) (D)
APNI KAKSHA 1
Q.10 The correct IUPAC name of the compound

(A) 5-Ethyl-3, 6-dimethyl non-3-ene
(B) 5-Ethyl-4, 7-dimethyl non-3-ene
(C) 4-Methyl-5, 7-diethyl oct-2-ene
(D) 2,4-Ethyl-5-methyl oct-2-ene
Q.11 The IUPAC name of
(A) 1-Cyclohexyl-3-methylpent-1-ene
(B) 3-Methyl-5-cyclohexylpent-1-ene
(C) 1-Cyclohexyl-3-ethylbut-1-ene
(D) 1-Cyclohexyl-3,4-dmethyl-but-1-ene
Q.12 IUPAC name of is:
(A) But-2-ene-2,3-diol (B)Pent-2-ene-2,3-diol

(C) 2-Methylbut-2-ene-2,3-diol (D) Pent-3-ene-3,4-diol
Q.13 IUPAC name of 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐍 is:

(A) Ethenenitrile (B) Vinyl cyanide
(C) Cyono ethene (D) Prop-2-enenitrile
(A) N-Methyl-N-ethyl ethanamine (B) Diethyl methanamine

(C) N-Ethyl-N-methyl ethanamine (D) Methyl diethyl ethanamine
Q.15 The IUPAC name of acetyl acetone is:

(A) Pentane-2,5-dione (B)Pentane-2,4-dione
(C) Hexane-2,4-dione (D)Butane-2,4-dione
Q.16 When vinyl & allyl are joined each other, we get
(A) Conjugated alkadiene (B) cumulative alkadiene
(C) Isolated alkadiene (D) Allenes
APNI KAKSHA 2
Q17. (a) and (b)
True statement for the above compounds is:

(A) (a) is phenol while (b) is alcohol
(B) Both (a) and (b) are primary alcohol
(C) (a) is primary and (b) is secondary alcohol
(D) (a) is secondary and (b) is primary alcohol
Q.18 The IUPAC name of the following structure (𝐂𝐇𝟑 ) C.C.C. (𝐂𝐇𝟑 )𝐂𝐇(𝐂𝐇𝟑 ) is:
(A) 3-Methylhex-4-yn-2-ene
(B) 3-Methylhex-2-en-4-yne
(C) 4-Methylhex-4-en-4-yne
(D) all are correct
Q.19 The IUPAC name of the following structure is [𝐂𝐇𝟑 𝐂𝐇(𝐂𝐇𝟑 )]𝟐 𝐂(𝐂𝐇𝟐 𝐂𝐇𝟑 )𝐂(𝐂𝐇𝟑 )𝐂𝟐 𝐂𝐇𝟐 𝐂𝐇𝟑 )𝟐
(A) 3,5-Diethyl-4,6-dimethyl-5-[1-methylethyl ] hept-3-ene
(B) 3,5-Diethyl-5-isopropyl-4,6-dimethylhept-2-ene
(C) 3,5-Diethyl-5-propyl-4,6-dimethylhept-3-ene
(D) None of these
Q.20 The correct IUPAC name of is:
(A) 2-Methyl butanoic acid (B) 2-Ethylprop-2-enoic acid

(C) 2-Carboxybutene (D) None of the above
Q.21 The correct IUPAC name of 2-ethylpent-3-yne is:

(A) 3-Methyl hex-4-yne (B) 4-Ethyl pent-2-yne
(C) 4-methyl hex-2 yne (D) None of these
Q.22 All the following IUPAC names are correct except:

(A) 1-Chloro-1-ethoxy propane (B) 1-Amino-1-ethoxypropane
(C) 1-Ethoxy-2-propanol (D) 1-Ethoxy-1-propanamine
Q.23 The IUPAC name of the compound 𝐂𝐇𝟑 𝐂𝐇 = 𝐂𝐇𝐂𝐇 = 𝐂𝐇𝐂 ≡ 𝐂𝐂𝐇𝟑 is:
(A)Octa-4,6-diene-2-yne (B)Octa-2,4-diene-6-yne
(C) Oct-2-yne-4,6-diene (D) Oct-6-yne-2,4-diene
APNI KAKSHA 3
Q.24 The correct IUPAC name of
(A) 3-Cyclohexanol Propyne

(B) 3-[3-Hydroxy Cyclohexyl] Propyne
(C) 3-Propynyl Cyclohexanol
(D) 3-(2-propynyl) Cyclohexanol
Q.25 The IUPAC name of 𝛃-ethoxy- 𝛂-hydroxy propionic acid (trivial name) is:
(A) 1,2-Dihydroxy-1-oxo-3-ethoxy propane
(B) 1-Carboxy-2-ethoxy ethanol
(C) 3-Ethoxy-2-hydroxy propanoic acid
(D) All above
Q.26 As per IUPAC rules, which one of the following groups, will be regarded as the principal
functional group?
(A) −𝐂 ≡ 𝐂 − (B) −𝐎𝐇 (C) (D)
Q.27 The IUPAC name of the compound is:
(A) 4-Pro-1-enyl hepta-1,6-diene (B) 4-Propylidene hepta-1,6-diene

(C) 4-Propenyl hepta-1,6-diene (D) 4-Prop-2-enyl hepta-1,6-diene
Q.28 The IUPAC name of the given compound is:
(A) 1,1-Dimethyl-3-hydroxy cyclohexane

(B) 3,3-Dimethyl-1-hydroxy cyclohexane
(C) 3,3-Dimethylcyclohexanol
(D) 1,1-Dimethylcyclohexan-3-ol
Q.29 The IUPAC name of is
(A) 2-Chloro-4-N-ethylpentanoic acid (B) 2-Chloro-3-(N,N-diethyl amino)-propanoic acid

(C) 2-Chloro-2-oxo diethylamine (D) 2-Chloro-2-carboxy-N-ethyl ethane
APNI KAKSHA 4
Q.30 The IUPAC name of the compound is
(A) 1-Amino-1-phenyl-2-methyl propane

(B) 2-Methyl-1-phenyl propan-1-amine
(C) 2-Methyl-1-amino-1-phenyl propane
(D) 1-Isopropyl-1-phenyl methyl amine
Q.31 Which of the following compound is wrongly named?
(A) ; 2-Chloro pentanoic acid
(B) ; 2-Methyl hex-3-enoic acid
(C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇 = 𝐂𝐇𝐂𝐎𝐂𝐇𝟑 ; Hex-3-en-2-one

(D) ; 4-Methyl pentanal
Q.32 The correct IUPAC name of the following compound is:
(A) 3,3-Diformylpropanoic acid

(B) 3-Formyl-4-oxo-butanoic acid
(C) 3,3-Dioxo propanoic acid
(D) 3,3-Dicarbaldehyde propanoic acid
Q.33 The correct IUPAC name of compound:
(A) 2-Cyano-3-oxopentanal (B) 2-Formyl-3-oxopentanenitrile

(C) 2-Cyanopentane-1,3-dione (D) 1,3-Dioxo-2-cyanopentane
Q.34 IUPAC name of compound
(A) 2, 3-diethyl butane (B) 2-ethyl-3-methyl pentane

(C) 3-methyl-2-ethyl pentane (D) 3,4-dimethyl hexane
APNI KAKSHA 5
Q.35 The IUPAC name of compound is
(A) 3,5-Dimethyl-4-Formyl pentanone (B) 1-Isopropyl-2-methyl-4-oxo butanal

(C) 2-Isopropyl-3-methyl-4-oxo pentanal (D) None of the above
Q.36 The IUPAC name of compound is
(A) 2-Amino-3-chloro-2-methylpent-2-enoic acid

(B) 3-Amino-4-chloro-2-methylpent-2-enoic acid
(C) 4-Amino-3-chloro-2-methylpent-2-enoic acid
(D) All of the above
Q.37 The IUPAC name of the structure is:
(A) 3-Amino-2-formyl butane-1, 4-dioic acid

(B) 3-Amino-2,3-dicarboxy propanal
(C) 2-Amino-3-formyl butane-1, 4-dioic acid
(D) 1-Amino-2-formyl succinic acid
Q.38 One among the following is the correct IUPAC name of the compound
(A) N-Formyl aminoethane (B) N-Ethyl formyl amine

(C) N-Ethyl methanamide (D) Ethylamino methanal
Q.39 The IUPAC name of the structure is:
(A) 1,2-Dimethyl-Cyclohexane (B) 1,6-Dimethyl-Cyclohexene

(C) 1,2-Dimethyl-Cyclohex-2-ene (D) 2,3-Dimethyl-Cyclohexane
Q.40 The IUPAC name of 𝐂𝟔 𝐇𝟓 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐎𝐎𝐇 is:
(A) Cinnamic acid (B) 1-Phenyl-2-carboxy ethane
(C) 3-Phenyl prop-2-enoic acid (D) Dihydroxy-3-phenyl propionic acid
APNI KAKSHA 6
Q.41 The IUPAC name of is:
(A) 2-Bromomethyl-3-oxohexanamide (B) 1-Bromo-2-amino-3-oxohexane

(C) 1-Bromo-2-amino-n-propyl ketone (D) 3-Bromo-2-propyl propanamide
Q.42 IUPAC name will be
(A) 1,2,3-Tricyano propane (B) Propane-1,2,3-trinitrile

(C) 1,2,3-Cyano propane (D) Propane-1,2,3-tricarbonitrile
Q.43 The IUPAC name of compound
(A) 3-Carbonyl methoxy -5- Ethanoyl oxy cyclohexanic aicd

(B) 3-Ethanoyl oxy -5- Methoxy carbonyl cyclohexane carboxylic acid
(C) 5-Ethanoyl oxy -5-Methoxy carbonyl cyclohexanoic aicd
(D) 3-Methoxy carbonyl -5- Ethanoyl oxy cyclohexane carboxylic aicd
(A) 1-Acetoxy acetic acid (B) 2-Acetoxy ethanoic acid

(C) 2-Ethanoyloxyacetic acid (D) 2-Ethanoyloxyethanoic acid
Q45.
The correct IUPAC systematic name of the above compound is:

(A) 2-Acetoxy ethanoic acid (B) 2-Methoxy carbonyl ethanoic acid
(C) 3-Methoxy formyl ethanoic acid (D) 2-Methoxy formyl acetic acid
(A) 3-Methyl cyclobut-1-ene-2-ol (B) 4-Methyl cyclobut-2-ene-1-ol

(C) 4-Methyl cyclobut-1-ene-3-ol (D) 2-Methyl cyclobut-3-ene-1-ol
(A) 2-Methoxy-4-nitro benzaldehyde (B) 4-Nitro anisaldehyde

(C) 3-Methoxy-4-formyl nitro benzene (D) 2-Formyl-4-nitro anisole
APNI KAKSHA 7
Q.48 The IUPAC name of compound
(A) 2-(Hydroxy methyl) methyl propanedioate

(B) Methyl-2-(hydroxy methyl) propanedioate
(C) 2-(Hydroxy methyl) dimethyl propanedioate
(D) None of these
(A) 2-Formyl ethanoic propanoic Anhydride

(B) 2-Oxo-propanoic prop-2-enoic Anhydride
(C) Prop-2-enoic-2-formyl propanoic Anhydride
(D) 2-Formyl ethanoic prop-2-enoic Anhydride

(A) 4,4-Di(formylmethyl) butanal
(B) 2-(Formylmethyl) butane-1, 4-dicarbaldehyde
(C)Hexane-3-acetal-1, 6-dial
(D) 3-(Formylmethyl) hexane-1, 6-dial
(A) 2-Chlorocarbonyl ethylbenzoate (B) 2-Carboxyethyl benzoyl chloride

(C) Ethyl-2-(chlorocarbonyl)benzoate (D) Ethyl-1-(chlorocarbonyl)benzoate
(A)Phenyl ethenone (B) Methyl phenyl ketone

(C) Acetophenone (D) Phenyl methyl ketone
Q.53 Structural formula of isopropyl methanoate is:
(A) (B)
(C) (D)
APNI KAKSHA 8
EXERCISE – II
Q.1 Q.2
Q.3 Q.4
Q.5 Q.6
Q.7 Q.8
Q.9 Q.10
Q.11 Q.12
Q.13 Q.14
Q.15 Q.16
Q.17 Q.18
Q.19 Q.20
APNI KAKSHA 9
Q.21 Q.22
Q.23 Q.24
Q.25 Q.26
Q.27 Q.28
Q.29 Q.30
Q.31 Q.32
Q.33 Q.34
Q.35 Q.36
Q.37 Q.38
Q.39 Q.40
APNI KAKSHA 10
Q.41 Q.42
Q.43 Q.44
Q.45 Q.46
Q.47 Q.48
Q.49 Q.50
Q.51 Q.52
Q.53 Q.54
Q.55 Q.56
Q.57 Q.58
APNI KAKSHA 11
Q.59 Q.60
Q.61 Q.62
Q.63 Q.64
Q.65 Q.66
Q.67 Q.68
Q.69 Q.70
APNI KAKSHA 12
EXERCISE - III
Q.1 Which of the following pairs have absence of carbocyclic ring in both compounds?
(A) Pyridine, Benzene (B) Benzene, Cyclohexane
(C) Cyclohexane, Furane (D) Furane, Pyridine
Q.2 The commercial name of trichloroethene is:
(A) Westron (B) Perclene (C) Westrosol (D) Orlone
Q.3 A substance containing an equal number of primary, secondary and tertiary carbon atoms is:
(A) Mesityl Oxide (B) Mesitylene (C) Maleic acid (D) Malonic acid
Q.4 The IUPAC name of the compound Glycerine is
(A) 1,2,3-Tri hydroxy propane (B) 3-Hydroxy pentane-1,5-diol

(C) 1,2,3-Hydroxy propane (D) Propane-1,2,3-triol
Q.5 Which of the following is crotonic acid:
(A) 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐎𝐎𝐇 (B) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐎𝐎𝐇
(C) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐎𝐎𝐇 (D)
Q.6 The group of heterocylic compounds is:

(A) Phenol, Furane (B) Furane, Thiophene
(C) Thiophene, Phenol (D) Furane, Aniline
Q.7 Column – I Column - II
(Common Name) (Structural formula)
(A) Isooctane (P)
(B) Neopentane (Q)
(C) Ethylidene chloride (R)
(Geminal dihalide)
(D) Ethylene Dichloride (Vicinal dihalide) (S)
(T)
APNI KAKSHA 13
Q.8 Column - I Column - II
(A) Acetone (P)
(B) Acetaldehyde (Q)
(C) Crotonaldehyde (R)
(D) Acrolein (S)

(A) (P) Lactic acid (In milk)
(B) (Q) Glyoxal
(C) H2N – CH2 – COOH (R) Glyceraldehyde
(D) (S) Glycine
(T) Glycerol
(A) Fumaric acid (P)
(B) Adipic acid (Q)
(C) Maleic acid (R)
(D) Tartaric acid (S) 𝐂𝐎𝐎𝐇(𝐂𝐇𝟐 )𝟒 𝐂𝐎𝐎𝐇
APNI KAKSHA 14
(A) (P) Pyrrole
(B) (Q) Furan
(C) (R) Thiophene
(D) (S) Indol
Q.12 Column – I Column - II

(A) p-Cresol (P)
(B) p-Xylene (Q)
(C) Resorcinol (R)
(D) Quinol (S)
(E) Cat echol (T)
APNI KAKSHA 15
Q.13 Which of the following is not correctly matched:
(A) Lactic acid
(B) Tartaric acid
(C) Pivaldehyde 𝐂𝐇𝟑 𝐂(𝐂𝐇𝟑 )𝟐 𝐂𝐇𝐎
(D) Iso-octane
Q.14 Column - I Column – II
(A) (P) Phenanthrene
(B) (Q) Anthracene
(C) (R) Azulene
(D) (S) Napthalene
APNI KAKSHA 16
Exercise – IV
Q.1 The IUPAC name of the compound having the formula is:
(A) 3,3,3-trimethyl-1-propene (B) 1,1,1-trimethyl-2-propene

(C) 3,3-dimethyl-1-butene (D) 2,2-dimethyl-3-butene
Q.2 Write the IUPAC name of 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇 = 𝐂𝐇 ⋅ 𝐂𝐎𝐎𝐇 [JEE 1986]
Q.3 The IUPAC name of the compound 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐇(𝐂𝐇𝟑 )𝟐 is: [JEE 1987]
(A) 1,1-dimethyl-2-propene (B) 3-methyl-1-butene
(C) 2-vinyl propane (D) None of the above
Q.4 The number of sigma and pi-bonds in 1-butene 3-yne are: [JEE 1989]
(A) 5 sigma and 5 pi (B) 7 sigma and 3 pi
(C) 8 sigma and 2 pi (D) 6 sigma and 4 pi
Q.5 Write IUPAC name of following:
(A) (B)
Q.6 Write IUPAC name of succinic acid. [JEE 1994]

Q.7 The IUPAC name of 𝐂𝟔 𝐇𝟓 𝐂𝐎𝐂𝐥 is [JEE 2006]
(A) Benzoyl chloride (B) Benzene chloro ketone
(C) Benzene carbonyl chloride (D) Chloro phenyl ketone
Q.8 The IUPAC name of the following compound is [JEE 2009]
(A) 4-Bromo-3-cyanophenol (B) 2-Bromo-5-hydroxybenzonitrile

(C) 2-Cyano-4-hydroxybromobenzene (D) 6-Bromo-3-hydroxybenzonitrile
Q.9 The IUPAC name (s) of the following compound is (are) [JEE 2017]
(A) 4- methylchlorobenzene (C) 1-chloro-4-methylbenzene

(B) 4-chlorotoluene (D) 1-methyl-4-chlorobenzene
APNI KAKSHA 17
Q.10 What is the IUPAC name of the following compound? [JEE 2019]
(1) 3-Bromo-1, 2-dimethylbut-1-ene

(2) 3-Bromo-3-methyl-1, 2-dimethylprop-1-ene
(3) 3-Bromo-3-methyl-1, 2-dimethylprop-1-ene
(4) 4-Bromo-3-methylpent-2-ene
Q.11 The IUPAC name for the following compound is: [JEE 2019]
(1) 3,5-dimethyl-4-propylhept-6-en-1-yne
(2) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
(3) 3,5-dimethyl-4-propylhept-1-en-6-yne
(4) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne
Q.12. The IUPAC name of the following compound is: [JEE 2019]
(1) 4-Methyl 1-3-hydroxypentanoic (2) 2-Methyl 1-3-hydroxypentan-5-oic acid

(3) 4,4-Dimethyl 1-3-hydroxybutanoic acid (4) 3-Hydroxy-4-methylpentanoic acid
Q.13. The correct IUPAC name of the following compound is: [JEE 2019]
(1) 2-methyl 1-5-nitrol-1-chloro benzene (2) 3-chloro-4-methyl-1-nitro benzene

(3) 5-chloro-4-methyl-1-nitro benzene (4) 2-chloro-1-methyl-4-nitro benzene
Q.14. Which one of the following structures has the IUPAC name 3-ethynyl-2-hydroxy-4-methylhex-
3-en-5-ynoic acid? [JEE Adv.-2020]
(1) (2) (3) (4)
APNI KAKSHA 18
-ESSENTIAL COMMON NAMES
ALKANE ALCOHOL
Isopentane Glycol or Ethylene Glycol
Isooctane Glycerol
CH2 = CH − CH2 − OH Allyl Alcohol

CH2 = CH − OH Vinyl Alcohol
ALKANE
CH2 = C = CH2 Allene ETHER
Isoprene C6 H5 − O − CH3 Anisole

(Methyl Phenyl Ether)
𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂 ≡ 𝐂𝐇 Vinyl acetylene KETONE
ALKYL HALIDE CH3 COCH3 Acetone
Westron (Solvent) CARBOXYLIC ACID
Malic acid
ClCH = CCl2 Westrosol or HOCHCOOH2 COOH Glycolic Acid

Triclean (Solvent)
CH3 − CHCl2 Ethylidene chloride Malonic acid

(gem dihalide)
Ethylene Dichloride(Vinyl dihalide) Succinic acid
CH2 Cl2 Methylene chloride Glutaric acid
CHCl3 Chloroform
CCl4 Carbontetra chloride
Cl2 C = CCl2 Tetraclean or Perclean
Chloropicrin (Tear gas)
Aceto Acetic Ester (AAE)

or Ethyl Aceto Acetate
APNI KAKSHA 19
Chloroprene
Catechol
Tartaric acid
Maleic acid Resorcinol
Fumaric acid Quinol
Citric acid Toluene
N–DERIVATIVES
CH3–CH=CH–COOHK Crotonic acid Pyrrole
Ph–CH=CH–COOH Cinnamic acid Furan
𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂 ≡ 𝐍 Vinyl Cyanide

or Acrylo Nitrile
Guanidine
AROMATIC COMPOUNDS
APNI KAKSHA 20
Benzene Salicylic acid

Amidine
Benzamide Salicylaldehyde
Benzyl alcohol (Aliphatic alcohol) Guanidine
Amidine
Phenol (Aromatic alcohol ) Anthracene
Thiophene
Toluic acids
Phthalic acid
Sulphanilic acid
Azulene Isophthalic acid
Napthalene Terephthalic acid
APNI KAKSHA 21
Anthranilic acid
Phenanthrene
(o-aminobenzoic acid)
Pyridine C6H5CHO Benzaldehyde
o–xylene Aniline
HETROCYCLIC COMPOUNDS
m-xylene Pyrrolidine
Nitrobenzene (oil of mirbane) Pyrrolidine
Orthanilic Acid Tetrahydrofuran (THF)
m-Cresol Oxirane or Ethylene Oxide or Oxo Cyclo Propane
𝐂𝟔 𝐇𝟓 𝐂𝐎𝟑 𝐇 Quinuclidine
SOME REAGENTS POLAR APROTIC SOLVENTS

Grignard’s reagent RMgX DMS Dimethyl sulphide 𝐂𝐇𝟑 − 𝐒 − 𝐂𝐇𝟑
APNI KAKSHA 22
NBS N-Bromosuccinimide DMSO Dimethyl sulphoxide Me2 S = O
HMPT Hexamethylphosphoramide
or
POLAR PROTIC SOLVENTS HMPTA O = P − (NMe2 )3
H−O−H Water DMF Dimethyl formamide
R−O−H Alcohol
Phenol Crown ethers Cyclic polyethers
Acetic acid
HF Hydrogen Fluoride
NH3 Ammonia
SOME GROUPS
Ts Tosyl
Ms Mesyl
Ac Acyl
Bs Brosyl
Tf Triflate
APNI KAKSHA 23
DESIRABLE COMMON NAMES-
APNI KAKSHA 24
APNI KAKSHA 25
APNI KAKSHA 26
EXERCISE – I
Q.1 (B) Q.2 (B) Q.3 (D) Q.4 (D) Q.5 (C) Q.6 ()
Q.7 (A) Q.8 (D) Q.9 (A) Q.10 (A) Q.11 (A) Q.2 (B)
Q.13 (D) Q.14 (C) Q.15 (B) Q.16 (C) Q.17 (D) Q.18 (B)
Q.19 (A) Q.20 (B) Q.21 (C) Q.22 (B) Q.23 (B) Q.24 (D)
Q.25 (C) Q.26 (D) Q.27 (D) Q.28 (C) Q.29 (B) Q.30 (B)
Q.31 (B) Q.32 (B) Q.33 (B) Q.34 (D) Q.35 (C) Q.36 (B)
Q.37 (C) Q.38 (C) Q.39 (B) Q.40 (C) Q.41 (A) Q.42 (D)
Q.43 (B) Q.44 (D) Q.45 (B) Q.46 (B) Q.47 (A) Q.48 (B)
Q.49 (D) Q.50 (D) Q.51 (C) Q.52 (A) Q.53 (D)
EXERCISE – II
Q.1 4-Ethyl octane
Q.2 3-Ethyl-2,4-dimethyl pentane
Q.3 5-Methyl hepta-1,3,6-triene
Q.4 Hepta-1,5-dien-3-yne
Q.5 2-Isopropyl-4-methylpent-1-ene
or 4-Methyl-2-(methyl ethyl) pent-1-ene
Q.6 3-Methoxyprop-1-ene
Q.7 1-Hydroxybut-3-en-2-one
Q.8 2-Ethylbut-2-en-1-ol
Q.9 3-nitroprop-2-en-1-ol
Q.10 4-hydroxyhex-5-en-1-yn-3-one
Q.11 4,6-Bis-[1,1-Dimethyl ethyl]
Nonane
Q.12 2-Formyl pentane nitrile
Q.13 2,2,6,7-tetramethylocatane
Q.14 3-Ethyl-4,6-dimethyloctane
Q.15 5 Methyl cyclohexa-1,3-diene
Q.16 4-Ethyl Pent-4-en-2-amine
Q.17 1,2-epoxy propane
Q.18 1,3,4-trimethyl-1-cyclobutene
Q.19 Methylene cyclohexane
Q.20 1-ethyl-2-methylcyclopentane
Q.21 1-methyl-3-(methyl ethyl cyclohexane)
or 3-isopropyl-1-methylcyclohexane
Q.22 Butyl cyclohexane
APNI KAKSHA 27
Q.23 Isopropylidenecyclopentane or 1-methyl ethylidene cyclopentane
Q.24 3-Bromo-4-cyclopropyl cyclopentane carboxylic acid
Q.25 Cyclopent-2-en-1-one
Q.26 1-(3-butenyl) cyclopentene
Q.27 1,2-diethenyl cyclohexene
Q.28 1-cyclohexyl-1-propanone
Q.29 Ethyl cyclohexanecarboxylate
Q.30 4-Bromo-2-ethyl cyclopentanone
Q.31 3-(hydroxymethyl)-5-methylheptanal
Q.32 2-Bromo-6-oxocyclohexanecarbaldehyde
Q.33 5-amino-6(1-methyl propyl) cyclo-hex-2-enol
Q.34 2-bromo-2-methyl cyclopentanone
Q.35 Methyl-2-methoxy-6-methyl-3-cyclohexene carboxylate
Q.36 Bicylo(2.2.1)heptane
Q.37 9-methyl bicyclo(4.2.1) nonane
Q.38 Bicyclo [𝟑, 𝟐, 𝟐] Non-6-one
Q.39 spiro(4.5) decane
Q.40 2-Methyl Benzoyl Chloride
Q.41 1,3,3-Trimethyl cyclohexene
Q.42 𝐁𝐢𝐜𝐲𝐜𝐥𝐨 (𝟐. 𝟐. 𝟏) heptane
Q.43 8-chloro bicyclo(4.2.0) oct-2-ene
Q.44 2-cyclopenten-1-ol
Q.45 Ethyl-2-oxo-cyclo pentane
carboxylate
Q.46 2-Formyl Benzoic acid
Q.47 3-Mthyl Benzoic acid
Q.48 Cyclohex-2-en-1,4-dione
Q.49 2-ethynyl cyclohexanol
Q.50 4-chloro-1-cyclopentylpentane-2-one
Q.51 1-Amino methyl-2-ethyl cyclohexanol
Q.52 1-propyl-4-isopropyl-1-cyclohexene or 4-(methyl ethyl)-1-propyl cyclohexene
Q.53 2-(2-oxo-cyclohexyl) propanoic acid
Q.54 3-ethoxy-1(1-nitrocyclohexyl)-hex-4-en-1-one
Q.55 1,3-diphenyl-1,4-pentadiene
Q.56 3-Formyl-2,5-dimethyl hexan-1-oic acid
Q.57 Isopropyl-2-hydroxy-7-methyl oct-5-en-1 -oate
APNI KAKSHA 28
Q.58 2-(Cycloprop-2-enyl)-5-methyl hex-1-ene
Q.59 Propyl-2,3-dihydroxy-2methyl butanoate
Q.60 3-Carbylamino-2-cyano-4-hydroxy-6mercapto heptandiamide
Q.61 2-Amido-6-chlorocarbonyl-3-methylidene6-oxo hex-4-enoic acid
Q.62 2-Amido/carbamoyl ethanoic acid
Q.63 3,7-Dimethyl-9-(2,2-dimethyl cyclohexyl) nona-2, 4, 6, 8-tetraen-1-ol
Q.64 Aminomethanoyl chloride
Q.65 Ethyl, chloromethanoate
Q.66 3-Formyl pentandioic acid
Q.67 7-Ethanoyloxy-3-ethoxylcarbonyl hepta-4, 6 dienoic acid
Q.68 2-Mercapto-4-methoxycyclopent-3-enol
Q.69 4-Ethoxy-3, 5, 7-trimethyl oct-2, 6 dienol
Q.70 2-Ethenyl-2-isocyano propan 1, 3 dinitrile
EXERCISE – III
Q.1 (D) Q.2 (C) Q.3 (B) Q.4 (D) Q.5 (C) Q.6 (B)
Q.7 (A) → Q, (B) → S, (C) → T, (D) → P Q.8 (A) → Q, (B) → S, (C) → R, (D) → P
Q.9 (A) → Q, (B) → S, (C) → T, (D) → P Q.10 (A) → Q, (B) → S, (C) → R, (D) → P
Q.11 (A) → T, (B) → P, (C) → S, (D) → Q Q.12 (A) → R, (B) → S, (C) → T, (D) → Q, (E) → P
Q.13 (D) Q.14 (A) → Q, (B) → S, (C) → P, (D) → R
EXERCISE – IV
Q.1 (C)
Q.2
Q.3 (B) Q.4 (B) Q.5 (a) 5,6-diethyl-3-methyl-dec-4-ene
Q.6 N,N, 3-trimethyl-3-pentanamine Q.7 (C) Q.8 (B) Q.9 (B, C) Q.10 (4)
Q.11 (3) Q.12 (4) Q.13 (4) Q.14 (D)
APNI KAKSHA 29
EXERCISE # I
1. Which of the following is false order of- I effect?
 
(A) –F > –Cl > –Br > –I (B) – NH3  – NH3  –NO2
(C) –F > –OH > –NH2 (D) > C  > CH > –H
2. What is the correct order of inductive effect?

(A) –O– > –CH3 > –CMe3 (B) –CO2- > –O– > CHMe2
–
(C) –O > –CH2Me > –D > –H (D) None
3. Which of the following groups have + I effect:
(A) (B) (C) (D) –CH = CH2
4. Which of the following groups have - I effect :

(A) –OH (B) – C– OH (C) –CH3 (D) –OCH3
||
O
5. How many of the following groups have+ I effect :


(a) –OH (b) –O (c) –NH2 (d) – N H
(e) –COOH (f) –COO (g) –Me (h) –OMe

(i) –F (j) – N H3
6. Which of the following statements is (are) true about resonance.

(a) Resonance is an intramolecular process.
(b) Resonance involves delocalization of both  and  electrons.
(c) Resonance involves delocalization of  electrons only.
(d) Resonance decreases potential energy of an acyclic molecule.
(e) Resonance has no effect on the potential energy of a molecule.
(f) Resonance is the only way to increase molecular stability.
(g) Resonance is not the only way to increase molecular stability.
(h) Any resonating molecule is always more stable than any non resonating molecule.
(i) The canonical structure explains all features of a molecule.
(j) The resonance hybrid explains all features of a molecule.
(k) Resonating structures are real and resonance hybrid is imaginary.
(l) Resonance hybrid is real and resonating structures are imaginary.
(m) Resonance hybrid is always more stable than all canonical structures.
47
7. Which of the following statement is incorrect?
(A) Resonating structure are real & have real existence
(B) Equivalent contributing structures make resonance hybrid very stable.
(C) Contributing structures are hypothetical having no real existence
(D) Contributing structures are less stable than the resonance hybrid.
8. Which of the following is most stable?

(A) Conjugated alkadiene (CH2 = CH–CH = CH2)
(B) Isolated alkadiene (CH2 = CH–CH2–CH = CH2)
(C) Cumulated alkadiene (CH2 = C = CH2)
(D) All are equally stable
9. Consider structural formulas A, Band C:

   
H 2C– N  N H2 C N N H2C– N  N
(A) (B) (C)
(a) Are A, B and C isomers, or are they resonance forms?
(b) Which structures have a negatively charged carbon?
(c) Which structures have a positively charged carbon?
(d) Which structures have a positively charged nitrogen?
(e) Which structures have a negatively charged nitrogen?
(f) What is the net charge on each structure?
(g) Which is a more stable structure, A or B? Why?
(h) Which is a more stable structure, B or C? Why?
l0. A canonical structure will be more stable if

(A) it involves cyclic delocalization of (4n + 2)-electrons than if it involves acyclic
delocalization of (4n + 2)  - electrons.
(B) it involves cyclic delocalization (4n-electrons than if it involves acyclic delocalization of
(4n) 7-electrons.
(C) +ve charge is on more electronegative atom than if +ve charge is on less electronegative
atom provided atoms are in the same period.
(D) –ve charge is on more electronegative atom than if –ve charge is on less electronegative
atom provided atoms are in the same period.
48
11. Which one of the following pair of structures does not represent the phenomenon of resonance?
O O–
||  |
(A) H2C  CH – C– H; C H 2 – CH – C – H
 
(B) CH3 CH
 – CHCl;CH2 – CH CH – Cl
O O–
|| |
(C) (CH3 )2 CH – C– O – ;(CH3 )2 CH – C  O
O O–
|| |
(D) (CH3 )2 CH 2 – C– CH3 ;CH3 – CH
 C CH3
12. In which of the following, lone-pair indicated is involved in resonance:
(a) (b) (c) (d)

(f) CH2 CH
(e) CH2  CH – CH2   – CH NH
13. In which of the following lone-pair indicated is not involved in resonance :

 
(a) CH2  CH – NH– CH3 (b)
 CH2 CH
 – CH O


(c) CH2 CH
  – O– CH CH2 CH2 CH – C  N
(d)

CH2
(e) (f)
O O
14. Which of the following groups cannot participate in resonance with other suitable group:

(a) –COOH (b) –COOCH3 (c) –COCl (d) – N H3

(e) – CH2
15. Identify electron donating groups in resonance among the following :

(a) –CONH2 (b) –NO2 (c) –OCOCH3 (d) –COOCH3
(e) –CHO (f) –NHCOCH3
16. Identify electron withdrawing groups in resonance among the following :

(a) –COOH (b) –CONHCH3 (c) –COCl (d) –CN
(e) –O–CH= CH2 (f)
49
17. Which of the following groups can either donate or witl).draw a pair of electrons in resonance
depending upon situation :
(a) –NO2 (b) –NO (c) –CH=CH2 (d) –CHO
(e) –NH2 (f) –N = NH
18. Draw the resonance forms to show the delocalization of charges in the following ions
O O
||  || 
(a) CH3 – C– CH2 (b) H – C– CH  CH– CH2 (c) (d)
(e) (f) (g) (h)
 
(i) CH
3 – CH CH
 – CH CH – CH – CH3 (j) CH
3 – CH CH
 – CH CH – CH2
19. Identify less stable canonical structure in each of the following pairs:
 
(a) CH2 – O – CH3 
CH2  O– CH3 (b)
(c) (d)
(e)
20. Identify more stable canonical structure in each of the following pairs :
(a) (b)
(c) (d)
 
(e) CH
2 – CO CH – O 
CH2 CH
  – CH O (f)
50
21. Which of the following group can participate in resonance With other suitable group:
— 
(a) –OH (b) –CH2 – CH2 (c) –CH2 – CH2 (d)

(e) (f) –BH2 (g) – PPh3
22. Arrange the following resonating structure according to their contribution towards resonance
hybrid?
        
(a) CH2 N N (b) CH2 – N  N (c) CH 2 – N  N (d) CH2 – N  N

(A) a > d > c > b (B) b > a > c > d (C) a > c > b > d (D) d > a > b > c
23. In each of the following pairs of resonating structure which resonating structure is more stable:
 —
 


(a) CH3 – CH – C  N   CH3 – CH   C N – 
 
 
(b)
(c)
24. Formic acid is considered as a hybrid of the four structures
Which of the following order is correct for the stability of four contributing structures?
(A) I > II > III > IV (B) I > II > IV > III (C) I > III > II > IV (D) I > IV > III > II
25. In the given pair of compounds select the one in each pair having lesser resonance energy :
(a) (b)
(c) (d)
51
26. Resonance energy of resonance hybrid of a molecule will be more if:
(a) canonical structures are equivalent than if canonical structures are non-equivalent
(b) molecule is aromatic than if molecule is not aromatic.
27. In the given pair of compounds select the one in each pair having higher resonance energy :
(i) (ii) CH2 = CH – O – CH = CH2 and CH2 = CH – NH – CH = CH2
 
(iii) CH2 CH
  – NHand HN CN – NH (iv) CH2 = CH – F and CH2 = CH – Br

(v) and CH2  CH – CH2 (vi)
(vii) (viii)
(ix) CH2 = CH – OH and CH2 = CH – CH = CH – OH

(x) (xi) CH3COOH and CH3COONa

(xii) CH2  CH – O and CH2 = CH – OH (xiii)
(xiv) (xv) and CH2=CH – CH=CH – CH=CH2
28. In the given pair of compounds select the one in each pair having lesser resonance energy :
(a) CO32– and HCOO– (b) and CH2 = CH – CH2–

(c) and CH2 = CH – CH – CH2 (d) and CH2 = CH – CH2
(e)
29. In which of the following pairs first one is having more resonance energy than the second one –
(A) (B)
(C) (D) None of these
52
30. In which of the following molecules  - electron density in ring is minimum:
(A) (B) (C) (D)
31. In which of the following molecules  -electron density in ring is maximum:
(A) (B) (C) (D)
32. Arrange following compounds in decreasing order of reactivity of ring towards attack of
electron deficient species –
(i) (ii) (iii) (iv)
(A) i > ii> iii > iv (B) iii> iv> ii> i (C) i >iv > ii > iii (D) i > ii> iv> iii
33. In which of the following molecule all the effect namely inductive, mesomeric &
hyperconjugation operate:
(A) (B) (C) (D)
34. Which one of the following molecules has all the effect, namely inductive, mesomeric and
hyperconjugative?
(A) CH3Cl (B) CH3–CH = CH2
(C) CH3 – CH  CH – C– CH3 (D) CH2 = CH – CH = CH2
||
O
35. Select the correct statement.

(i) Delocalisation of -electron is hyperconjugation.
(ii) Delocalisation of -electron is resonance.
(iii) Permanent partial displacement of -electron is inductive effect.
(A) i & iii (B) ii & iii (C) i & ii (D) i, ii, iii
53
36. Which of the following compound is correctly matched with number of hyperconjugating
structures (involving C–H bond) :
(A) (3) (B) (9) (C) (8) (D) CH3–CC–CH3 (5)
37.
These are three canonical structures.of naphthalene. Examine them and find correct statement
among the following :
(A) All C–C bonds are of same length (B) C1–C2 bond is shorter than C2–C3 bond.
(C) Cl–C2 bond is longer than C2–C3 bond (D) None
38. Which of the following has longest C–O bond:
(A) (B) (C) (D)
39.
Among these compounds, the correct order of C–N bond lengths is :

(A) IV > I > II > III (B) III > I > II > IV (C) III > II > I > IV (D) III > I > IV > II
40. Cl–C2 bond is shortest in
(A) (B) (C) (D)
41. Which of the following molecule has longest C=C bond length?
(A) CH2=C=CH2 (B) CH3–CH=CH2 (C) (D) CH3 – C  CH2

|
CH3
54
42. Which of the following molecule has shortest C=C bond length ?
(A) CH2=C=CH2 (B) CH3–CH=CH2 (D) (D) CH3 – C  CH2

|
CH3
43. C–C and C=C bond lengths are unequal in:
(A) Benzene (B) 1,3-buta-di-ene (C) 1,3-cyclohexa-di-ene (D)
44. Among the following molecules, the correct order of C–C bond length is (C6H6 is benzene)
(A) C2H6 > C2H4 > C6H6 > C2H2 (B) C2H6 > C6H6 > C2H4 > C2H2
(C) C6H4 > C2H6 > C2H2 > C6H6 (D) C2H6 > C2H4 > C2H2 > C6H6
45. CH3O–CH= CH–NO2 I

CH2 =CH–NO2 II
CH2 = CH–Cl III
CH2 = CH2 IV
Which of the following is the correct order of C–C bond lengths among these compounds:
(A) I > II > III > IV (B) IV > III > II > I (C) I > III > II > IV (D) II > III > I > IV
46. Which of the following is (are) the correct order of bond lengths:
(A) C–C > C = C > C  C > C  N
(C) C = C > C = N > C = O
(B) C = N > C = O > C = C
(D) C–C > C = C > C  C > C–H
47. In which of the following pairs, indicated bond having less bond dissociation energy:
(a) (b) CH3 – C  CHand HC  CH

 
(c)
(d) (e)
(f)
55
48. In which of the following pairs, indicated bond is of greater strength:
(a) CH3 – CH2 – Br andCH3 – CH2 – Cl
 
(b) CH3 – CH  CH – Br and CH3 – CH– CH3
 |
Br
(c) and CH3 – CH2 – Cl



(d) CH2 CH
 – CH CH2 and CH2  CH2 – CH2 – CH3
 

(e) CH2 CH
 – CH CH2 and CH2  CH – NO2
 
(f)
49.
the correct order of bond dissociation energy (provided bond undergoes homolytic cleavage):
(A) C2–H > C3– H > C4–H > C1–H (B) C2–H > C3–H > C1–H > C4
(C) C1–H > C4–H > C2–H > C3–H (D) C1–H > C4–H > C3–H > C2 – H
50. Compare the C–N bond-length in the .following species:
(A) (B) (C)
51. In which case, C–O bond length is shorter for Ist compound:
(A) (B)
(C) (D)
56
EXERCISE # II
1. In each set of species select the aromatic species.
(i)
(ii)
(iii)
(iv)
(e)
2. Which of the given compound is aromatic, antiaromatic or nonaromatic.
(a) (b) (c) (d)
(e) (f) (g)
57
3.
Compare carbon-carbon bond rotation across I, II, III.

(A) I > II > III (B) I > III > II (C) II > I > III (D) II > III > I
4. Which of the given compunds has minimum rotation energy barrier across indicated carbon-
carbon bond.
Compare carbon-carbon bond rotation across I, II, III.

(A) I > II > III (B) I > III > II (C) II > I > III (D) II > III > I
5 Which species is not aromatic?
(A) (B) (C) (D)
6 Which of the following are non-aromatic
(A) (B) (C) (D)
7. Write down the structure of the following molecule and comment on aromaticity?
(a) B3H3O3
(b) C3N3(NH2)3
(c) Trimer of isocyanic acid (HN = C = O)3
8. Select the least stable one :

(A) CH3 – CH2 (B) CH3 – CH2 – CH2
(C) (D)
58
9. Write stability in decreasing order of following intermediates:
CH3
  |
(i) (a) CH3 – CH2 (b) CH3 – CH – CH3 (c) CH3 – C
|
CH3
(ii)
(iii)
(iv)
  
(v) (a) CF3 – CH2 (b) CCl3 – CH2 (c) CBr3 – CH2
(vi)
  
(vii) (a) HC  C (b) CH2  CH (c) CH3 – CH2
(viii) (a) C6H5+ (b) p–NO2(C6H4)+ (c) p-CH3–(C6H4)+ ( d) p–Cl–C6H4+
(ix) (a) (b) (c)
(x) (a) (b) (c)
(xi) (a) (b) (c)
59
(xii) (a) (b) (c) (d)
Me Ph 

(xiii) (a) Me–C+ (b) Ph–C+ (c) Me – CH2 (d)
Me Ph
+
+
(xiv) (a) (b)
+
(c) (d)
(e) +
+
+ CH2
CH2 +
(xv) (a) (b) (c)
+ + +
(xvi) (a) (b) (c)
10. Consider the following statements:

 
(I) CH3OCH2 is more stable than CH3 CH2
 
(II) Me2 CH is more stable than CH3CH2 CH2
 
(III) CH2  CH –CH 2 is more stable than CH3CH2 CH2
 
(VI) CH2  CH is more stable than CH3 CH2
Of these statements:
(A) I and II are correct (B) III and IV are correct
(C) I, II and III are correct (D) II, III and IV are correct
60
11. In each of the following pairs of ions which ion is more stable:
 
(a) (I) C6H5 – CH2 and (II) CH2  CH – CH2
 
(b) (I) CH3 – CH2 and (II) CH2  CH
 
CH2 CH2
(c) (I) and (II)
CH3–CH–CH3 CH3–N–CH3
(d) (I) and
CH3–C–CH3 CH3–C–CH3
 
12. Find out correct stability order in the following carbocations-




(I) (II) (III) (IV)

(A) IV > I > III > II (B) IV > III > I > II (C) I > IV > III > II (D) I > III > IV > II
13. Which of the following carbonium ion is most stable ?

(A) Ph3C+ (B) (CH3)3C+ (C) (CH3)2 CH+ (D) CH2=CH–CH2+
14. Consider the following carbocations

 
(a) CH3O CH2 (b) CH2
 
(c) CH3 CH2 (d) CH3 – CH2
The relative stabilities of these carbocations are such that :-

(A) d < b < c < a (B) b < d < c < a (C) d < b < a < c (D) b < d < a < c
   
CH2 CH2 CH3 CH2
15.
OH NH3 CH3 CH3–C–CH3

CH3
Correct order of carbocation stability is :
(A) 2 > 1 > 4 > 3 (B) 1 > 2 > 4 > 3 (C) 3 > 4 > 2 > 1 (D) 2 > 1 > 3 > 4
61
16. Arrange the following carbocation in the increasing order of stability :
  
CH2 CH2 CH2
CH3
CH2–CH CH–CH3
CH3 NO2 CH3 NO2
(I) (II) (III)
(A) I < II < III (B) II < III < II (C) III < II < I (D) III < I < II
17. Rank the following sets of iritermediates in increasing order of their stability.
CH2 CH2
(i) (a) (b)
F NO2
CH2 CH2 CH2 CH2
(ii) (a) (b) (c) (d)

N
Cl O O CN
 
(iii) (a) CH2–CH (b) CH2 – CH3
O
O O O
(iv) (a) (b) (c)
  
– –
CH2 CH2– CH2
(v) (a) (b) (c)
Cl NO2
  
(vi) (a) (b) (c)
CH2 CH2–CH2
(vii) (a) (b) (c)
62
(viii) (a) (b) (c)
(ix) (a) (b)

 
(x) (a) CH2  CH (b) CH2  CH – CH2 (c) CH2 (d) CH3
18. Most stable carbanion is :-

(A) HCC (B) C6H5 (C) (CH3)3C–CH2 (D) (CH3)2C=CH
19. Most stable carbanion is :

 
CH2 CH2

(A) CH3 (B) CH2  CH – CH2 (C) (D)
NO2
20. Identify the most stable anion.

   
(A) (B) (C) (C)
O
O
21. Correct order of stability :
CH3
  
(A) > H3 C CH3 > CH2–OCH3 > CH3

(B) > >

   
CH2–CH2 CH2 CH2 CH2
(C) > > >
NO2 Br CH3
CH3   
(D) CH2=CH–C  CH
2 CH – CH2  CH3  CH2  CH
2 CH
CH3
63
22. Rank the following sets of intermediates in increasing order of their stability giving appropriate
reasons for your choice.
+ + +
+ O O O
(a)
+
O O O
O O O O
– – – –
(b) CH2–C–CH3 , CH2–C–H , CH2–C–NH2 , CH2–C–OCH3
23. Select the correct order of stability of carbon free radicals :

  
I. Ph – CH2 II. Ph – CH– CH2 – CH3

III. Ph – CH– CH  CH2 IV. Ph–C–CH=CH2
CH3
(A) IV > Ill > I > II (B) IV > III> II > I (C) I > II > III > IV (D) I> III > II > IV
24. CH2=CH–CH=CH–CH3 is more stable than CH3–CH=C=CH–CH3 because

(I) (II)
(A) there is resonance in I but not in II (B) there is tautomerism in I but not in II
(C) there is hyperconjugation in I but not in II (D) II has more cononical structures than I
25. Choose the more stable alkene in each of the following pairs. Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene
(b) Isopropenylcyclopentane or allylcyclopentane
(c) or
26. Match each alkene with the appropriate heat of combustion:

Heats of combustion (kJ/mol) : 5293 ; 4658; 4650; 4638; 4632
(a) 1-Heptene (b) 2,4-Dimethyl-l-pentene
(c) 2,4-Dimethyl-2-pentene (d) 4,4-Dimethyl-2-pentene
(e) 2,4,4-Trimethyl-2-pentene
27. Stability of:

CH3
(I) CH3–CH=CH–CH3 (II) CH3–C=C–CH3
CH3
(II) CH3–C=CH2 (IV) CH3–C=CH–CH3
CH3 CH3
in the increasing order is :
(A) I < III < IV < II (B) I < II < III < IV (C) I < IV < III < I (D) II < III < IV < I
64
28. Which of the following C–H bonds participate in hyperconjugation?
(A) I and II (B) I and IV (C) I and III (D) Ill and IV
29. Rank the following alkenes in decreasing order of heat of combustion values:
(I) (II) (III) (IV)

(A) II > III > IV > I (B) II > IV > III > I (C) I > III > IV > II (D) I > IV > III > II
30. Write decreasing order of heat of hydrogenation :
(i) (a) (b)
(c) (d)
(ii) (a) (b)
(c) (d)
(e)
CH3 CH3
(iii) (a) (b)
CH3 CH3
O O
(iv) (a) (b)
CH3 H CH3 CH3

(v) (a) C=C (b) C=C
H CH3 H H
CH3 CH3
(vi) (a) CH2=CH–CH (b) CH2=C
CH3 CH2–CH3
65
31. Write increasing order of heat of hydrogenation :
(i) (a) (b)
(ii) (a) (b) (c) (d) (e)
(iii) (a) (b) (c)
(iv) (a) (b) (c) (HOH per benzene ring)
32. Give decreasing order of heat of combustion (HOC):
(i) (a) (b) (c)
(ii) (a) (b) (c) (d)
(iii) (a) (b)
(iv) (a) (b) (c)
33. Among the following pairs identify the one which gives higher heat' of hydrogenation :
(a) and (b) and
(c) CH3–CH = CH–CH3 and CH3–CH2–CH= CH2

CH2 CH3
(d) and
CH3 CH3
34. Arrange the following compounds in order of:

(I) Stability (II) Heat of hydrogenation
(a) (b) (c) (d)
35. If Heat of hydrogenation of 1-butene is 30 Kcal/mol then heat of hydrogenation of 1, 3-

butadiene is ?
(A) 30 (B) 60 (C) 57 (D) 25
66
NMe2 NH2 SO3H NO2 Br
36.
A B C D E
Steric inhibition of resonance takes place :
(A) In A,B only (B) In A, B, C, E (C) C only (D) In A only
37. Consider the following two structures and choose the correct statements –
O– +
O –O
+
O
N N
(I) (II)
(A) carbon-nitrogen bond length structure I is greater than that in structure II
(B) carbon-nitrogen bond length in structure I is less than in structure II
(C) carbon-nitorogen bond length in both structure is same
(D) It cannot be compared
38. Which of the following statements would be true about this compound:
NO2
5
1 3
NO2 NO2
Br
(A) All three C–N bonds are of same length.
(B) Cl–N and C3–N bonds are of same length but shorter than C5–N bond.
(C) Cl–N and C3–N bonds are of same length but longer than C5–N bond.
(D) Cl–N and C3–N bonds are of different length but both are longer than C5–N bond
67
39. Arrange given compounds in decreasing order of dipole moment:
CH3 CH3 CH3
Cl
(i) (a) (b) (c)
Cl
Cl
NO2 NO2 NO2
Cl
(ii) (a) (b) (c)
Cl
Cl
NMe2 NMe2
(iii) (a) (b)
40. Why a cation like is not possible.
68
EXERCISE # III
1. Cyclopentadienyl anion is much more stable than allyl anion because :
(A) Cyclic anion is more stable than acyclic anion
(B) Delocalised anion is more stable than localised anion
(C) Cyclopentadienyl anion is aromatic in nature
(D) None of these
2. Select correct statement regarding given compounds :
CH3OCH3 C2H5OH
I II
(A) Boiling point of II is higher than I
(B) Boiling point of II is lower than I
(C) Compound I forms intramolecular H-bonding
(D) Compound II forms intermolecular H-bonding
I II III IV
3. In the compound, CH3–CH=CH–CN, the most electronegative carbon is :
(A) I (B) II (C) III (D) IV
 
CH2 CH2
4.
CH3 CD3
(I) (II)
Carbocation (I) is more stable than carbocation (II), because :
(A) –CD3 has more + I effect than –CH3 (B)–CH3 has more + I effect than –CD3
(C) –CH3 has more + H effect than –CD3 (D)–CD3 has more + H effect than –CH3
5. Select correct statement :
(A) Carbon-oxygen bonds are of equal length in acetate ion
(B) Resonating structures of acetate ion are equivalent
(C) Carbon-oxygen bonds are of unequal length in formate ion
(D) Resonating structures of formate ion are equivalent
6. Match the column I with column II.
Column-I Column-I
(Group attached with benzene ring) (Effect shown by the group)
(A) –NO2 (P) –R effect
(B) –O– (Q) +R effect
(C) –O–CH3 (R) +I effect
(D) –CN (S) –I effect
69
7. Column- I Column- I
(Groups attached to phenyl ring) (Effect shown)

(A) –N0 (P) +M
(B) –CH3 (Q) –M
O
(C) –NH–C (R) +H
CH3
(D) –C–OCH3 (S) –I
O
8. Match the column :

Column-I Column-II
(A) Group donate e– inductively but does not (P) –OH
donate/withdraw by resonance
(B) Group withdraw e– inductively but does not (Q) –NO2
donate/withdraw by resonance
(C) Group withdraw e– inductively & donate (R) –CH2–CH3
–
e by resonance

(D) Group withdraw e– inductively & withdraw (S) – NH3
e- by resonance
(T) –NH2
9. Match the column I with column II.

Column-I Column-II
(A) (P) Aromatic
(B) (Q) Non-aromatic
(C) + (R) Anti-aromatic


(D) (S) Cyclic structure
70
10. Statement-I : –C–OEt
a –C–O–C–
b bond length a < b
O O O
Because
Statement-II: More is the double bond character less is the bond length.
(A) Statement-I is true, statement-II is true and statement-II is correct explanation for statement-I.
(B) Statement-I is true, statement-II is true and statement-II is NOT the correct explanation for
statement-I.
(C) Statement-I is true, statement-II is false.
(D) Statement-I is false, statement-II is true.
   
11. Statement-I: Me3 C is more stable than Me2 CH and Me2 CH is more stable than the MeCH2 .
Because
Statement-II: Greater the number of hyperconjugative structures, more is the stability of carbocation.
(A) Statement-I is true, statement-II is true and statement-II is correct explanation for statement-I .
(B) Statement-I is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-I.
(C) Statement-I is true, statement-II is false.
12. Statement-I : The potential energy barrier for rotation about C=C bond in 2-butene is much
higher than that in ethylene.
Because
Statement-II : Hyperconjugation effect decreases the double bond character.
(A) Statement-I is true, statement-II is true and statement-II is correct explanation for
statement-I.
(B) Statement-I is true, statement-II is true and statement-II is NOT the correct explanation for
statement-I
(C) Statement-I is true, statement-II is false
Paragraph for Question 13 to 15
The intramolecular delocalisation of n and non-bonding electrons without any change in the
position of atoms is called resonance. Delocalisation may occur in conjugated system involving
carbon atom and atom other than carbon. Delocalisation makes system stable. More is the
number of resonating structures, more is the stability of the system. A resonating structure is
less stable when a higher electronegative atom has positive charge and when identical charges
are present on adjacent atoms.
13. The decreasing order of stability of the following resonating structures
 —   
CH2 CH – Cl
 

  CH2 – CH
   Cl 

 CH2 – CH 
  Cl –

  is:
(I) (II) (III)
(A) I > II > III (B) II > III > I (C) III > II > I (D) I > III > II
71
 
14. If A is PhCH2 and B is CH2  CH – CH2 , the greater number of resonating structure is of-
(A) A (B) B (C) both A and B (D) None of these
15. Which of the following pairs represent resonance?

 
(A) CH2 = CHOH ; CH3CHO (B) CH2 – CHO ;H2C  CH– O
+
O OH OH OH
(C) CH3–C–CH3 ; CH3–C=CH2 (D) CH3–C–CH3 ; CH3–C–CH3
Paragraph for Question 16 to 18

Carbocation is a specie with-positively charged carbon atom having six electrons irrthe valence
shell after sharing. Carbocations are formed in the heterolysis of a bond and are planar species.
Stability of carbocation is determined by inductive effect, hyperconjugation and resonance
effect Greater the number of contributing structures, more is the stability of a Carbocation.
Electron releasing groups (+I effect) increases the stability of a carbocation whereas the
electron withdrawing groups (–1 effect) have an opposite effect.
16. Which of the following is most stable carbocation?

   +
(A) CH3 (B) CH3 – CH– CH3 (C) CH3 – CH2 (D) CH3–C–CH3
CH3
17. The most stable carbocation among the following :

NO2

(A) (B)  (C)  (D) 
18. In which of the following cases, the carbocation (I) is less stable than the carbocation (II)?
+ +
 
CH2 CH2
(A) C6H5 – CH2 (I),CH2  CH – CH2 (II) (B) (I) , (II)
  + 
(C) CH2  CH(I), CH3 – CH2 (II) (D) H3C–CH2(I), CH2–CH2 (II)
CH3
72
19. Examine the structures I and II for nitromethane and choose the statement correctly:
–
+ O +2 O
CH3–N – CH3–N –
O O
(I) (II)
(A) Structure II is unlikely representation because electrons have shifted to oxygen
(B) Structure II is unlikely representation because nitrogen has sextet of electrons
(C) Structure II is acceptable and important
(D) None of these
20. Examine the following two structures for pyrrole and choose the correct statement given below
+
N N–
H H
(I) (II)
(A) II is not an acceptable resonating structure because carbonium ions is less stable than
nitride ion
(B) II is not an acceptable resonating structure because there is charge separation
(C) II is not an acceptable resonating structure because nitrogen has ten valance electrons
(D) II is an acceptable resonating structure
21. Delocalization of electrons increases molecular stability because :

(A) Potential energy of the molecule decreases (B) Electron-electron repulsion decreases
(C) Both (A) and (B) (D) Electron-electron repulsion increases
22. The most stable and the least stable carbocation among

  
(I) (II) CH2  CH– CH2 (III) C6H5 – CH2 (IV) CH3 – CH– CH3
are respectively :
(A) II, I (B) III, IV (C) I, II (D) I, IV
23. Most stable carbocation is formed by the heterolysis of:

(A) (CH3)3CBr (B) (C6H5)3CBr (C) (C6H5)2CHBr (D) C6H5CH2Br
73
24. Total number of aromatic compounds
HO O
(a) (b) (c) (d) 

N
HO O H H
O
(e) (f)
25. Identify total number of compounds which are unstable at room temperature ?
O
(i) (ii) (iii) (iv)
H
B
(v) (vi) (vii)
74
EXERCISE # IV (JEE-MAINS)
1. In the following benzyl/allyl system [AIEEE-2002]
R–CH=CH2 or R
(R is alkyl group)
decreasing order ofinductive effect is-
(1) (CH3)3C– > (CH3)2CH– > CH3CH2– (2) CH3–CH2– > (CH3)2CH– > (CH3)C–
(3) (CH3)2CH– > CH3CH2– > (CH3)3CH– (4) None of these
2. In the anion HCOO- the two carbon-oxygen bonds are found to be of equal length. What is the
reason for it- [AIEEE-2003]
(1) Electronic orbits of carbon atoms are hybridised
(2) The C=O bond is weaker than the C–O bond
(3) The anion HCOO– has two resonating structure
(4) The anion is obtained by removal of a proton form the acid molecule
3. Which one of the following does not have sp2 hybridised carbon [AIEEE-2004]
(1) Acetamide (2) Acetic acid (3) Acetonitrile (4) Acetone
4. Due to the presence of an unpaired electron, free radicals are - [AIEEE-2005]

(1) Chemically inactive (2) Chemically reactive
(3) Cations (4) Anions
5. The increasing order of stability of the following free radicals is [AIEEE-2006]

   
(1) (C6H5 )3 C  (C6H5 )2 CH  (CH3 )3 C  (CH3 )2 CH
   
(2) (C6H5 )2 CH  (C6H5 )3 C  (CH3 )3 C  (CH3 )2 CH
   
(3) (CH3 )2 CH  (CH3 )3 C  (C6H5 )3 C  (C6H5 )2 CH
   
(4) (CH3 )2 CH  (CH3 )3 C  (C6H5 )3 CH  (C6H5 )3 C
— — — —
6. Arrange the carbanions, (CH3 )3 C,CCl3 ,(CH3 )2 CH,C6H5 CH2 in order of their decreasing
stability [AIEEE-2009]
— — — —
(1) CCl3  C6H5 CH2  (CH3 )2 CH  (CH2 )3 C
— — — —
(2) (CH3 )3 C  (CH3 )2 CH  C6H5 CH2  CCl3
— — —
(3) C6H5 CH2  CCl3  (CH3 )3 C  (CH3 )2 CH
— — — —
(4) (CH3 )2 CH  CCl3  C6H5 CH2  (CH3 )3 C
75
7. The non aromatic compound among the following"is :- [AIEEE-2011]
(1) (2) (3) (4)

S 
8. ortho-Nitrophenol is less soluble in water than ir-and m- Nitrophenols because : [AIEEE-2012]

(1) Melting point of o-Nitrophenol is lower than those of m- and p–isomers
(2) o- Nitrophenol is more volatile in steam than those of m- and p–isomers
(3) o-Nitrophenol shows lntramolecular H–bonding
(4) o-Nitrophenol shows Intermolecular H–bonding
9. Which of the following compounds are antiaromatic :- [AIEEE-2012(0nline)]
(I) (II) (III) (IV)

O 
(V) (VI)

(l) (III) and (VI) (2) (II) and (V) (3) (I) and (V) (4) (V) and (VI)
10. Among the following the molecule with the lowest dipole moment is :- [AIEEE-2012(0nline)]
(1) CHCl3 (2) CH2Cl2 (3) CCl4 (4) CH3Cl
11. The order of stability of the following carbocations [JEE-MAIN-2013]


CH2
 
CH2=CH–CH2; CH3–CH2–CH2 ; is :
I II
III
(l) III > II > I (2) II > III > I (3) I > II > III (4) III > I > II
12. For which of the following molecule significant μ  0 (JEE-MAIN-2014]

Cl CN OH SH
(1) (2) (3) (4)
Cl CN OH SH
(1) Only (3) (2) (3) and (4) (3) Only (1) (4) (1) and (2)
13. Which of the following molecules is least resonance stabilized ? [JEE-MAIN-2017]
(1) (2) (3) (4)

O N O
76
14. Which of the following compounds is not aromatic ? [JEE MAIN-2019]
(1) (2) (3) (4)

N N
H
15. Which compound(s) out of the following is/are not aromatic ? [JEE MAIN-2019]
(1) (A) and (C) (2) (B), (C) and (C) (3) (C) and (D) (4) (B)
77
EXERCISE # V (JEE-ADVANCED)
l. Which one of the following has the smallest heat of hydrogenation per mole of H2? [IIT-93]
(A) 1–Butene (B) trans–2-Butene
(C) cis–2–Butene (D) I, 3–Butadiene
2. Most stable carbonium ion is [IIT-95]

 
(A) p – NO2 – C6H4 – CH2 (B) C6H5 CH2
 
(C) p – Cl – C6H4 – CH2 (D) p – CH3O – C6H4 – CH2
3. Arrange the following compounds in order of increasing dipole moment : [IIT-96]

toluene (I) m-dichloroobenzerie (II)
o-dichlorobenzene (III) p-dichlorobenzene (IV)
(A) I < IV < II < III (B) IV < I < II < III (C) IV < I < III < II (D) IV < II < I < Ill
4. The most unlikely representation ofresonance structure of p-nitrophenoxide ion is - [IIT-99]

       
O–N=O O–N–O O=N=O O–N=O
(A) (B) (C) (D)


O O O O
5. An aromatic molecule will not [IIT-99]
(A) have 4n  electrons (B) have (4n + 2) electrons
(C) be planar (D) be cyclic
6. Statement-I: p-Hydroxybenzoic acid has a lower boiling point that o-hydroxybenzoic acid.
Because
Statement-II: o-Hydroxybenzoic acid has intramolecular hydrogen bonding. [IIT-2003]
(A) Statement-I is True, Statement-II is True ; Statement-II is a correct explanation for Statement-I
(B) Statement-I is True, Statement-II is True ; Statement-II is NOT a correct explanation for
Statement-I
(C) Statement-I is True, Statement-II is False.
(D) Statement-I is False, Statement-IT is True.
7. Among the following, the molecule with the highest dipole moment is [IIT-2003]
(A) CH3Cl (B) CH2Cl2 (C) CHCl3 (D) CCl4
78
8. Give resonating structures of following compound. [IIT-2003]
OH
9 Which of the following is least stable : [IIT-2005]

   
(A) CH3 – C CH
  – CH– HC CH2 (B) CH
 3 –O CH
 – HC HC – CH2
   
(C) CH3 – O– CH– CH– HC  CH2 (D) CH3 – O– CH– CH– CH  CH2
10 Among the following, the least stable resonance structure is - [IIT-2007]


  O   O   O  O
 N  N  N  N
(A) O (B) O (C) O (D) O
   
11 The correct stability order for the following species is : [IIT-2008]

  
O O 
(I) (II) (III (IV

(A) II > IV > I > III (B) I > II > III > IV (C) II >)I > IV > III (D)
) I > III > II > IV
12 The correct stability order of the following resonance structures is [IIT-2009]

 —  — —  — 
(I) H2C N N (B) H2 C– N  N (C) H2 C– N  N (D) H2 C– N  N
(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)
13 The total number of contributing structures showing hyperconjugation (involving C-H bonds)
for the following carbocation is. [IIT-2011]
H3C  CH2CH3
14 Which of the following molecules, in pure from, is (are) unstable at room temperature?
[IIT-2012]
O O
(A) (B) (C) (D)
79
Q.15 The hyperconjugative stbilities of tert-butyl cation and 2-butene, respectively, are due to
(A) p (empty) and  electron delocalisations [IIT-2013]
(B)  and  electron delocalisations
(C) p (filled) and  electron delocalisations
(D) p (filled)  and  electron delocalisations
Q.16 The total number of lone-pairs of electrons in melamine is [IIT-2013]
Q.17 The number of resonance structures for N is : [IIT-2015]

OH
NaOH
N
Q.18 Among the following the number of aromatic compound(s) is [JEE ADV. 2017]
 
  
80
ANSWER KEY
EXERCISE # I
l. (D) 2. (C) 3. (B) 4. (A,B,D) 5. 4(b,d,f,g)
6. (a), (c), (d), (g), (j), (l), (m) 7. (A) 8. (A)
9. (a) Resonance forms, (b) A, (c) C, (d) A & B, (e) B & C, (f) 0, (g) B, (h) B
10. A,D 11. (D) 12. b,d,e 13. b,d,e 14. (d) 15. c,f
16. a,b,c,d,f 17. b,c,f 19. a-I, b-II, c-II, d-II, e-1
20. a-I,b-I,c-I,d-I,e-II,f-II 21. a,e,f,g 22. (A) 23. (a) II; (b) II; (c) II
24. (A) 25. a-II, b-II, c-II, d-II 26. a&b
27. (i)-I, (ii)-II, (iii)-II, (iv)-I, (v)-I, (vi)-II , (vii)-I, (viii)-II, (ix)-II, (x)-II, (xi)-II ,(xii)-I, (xiii)-I,
(xiv)-I, (xv)-I
28. a-II, b-I, c-I, d-II, e-I 29. (B) 30. (D) 31. (B) 32. (C)
33. (C) 34. (C) 35. (D) 36. (A,B,C)
37. (B) 38. (B) 39. (C) 40. (D) 41. (D) 42. (A)
43. (B,C,D) 44. (B) 45. (A) 46. (A,C,D)
47. a-I ,b-I, c-II, d-I, e-I, f-I 48. a-II ,b-I, c-I, d-I, e-II, f-II
49. (D) 50. C>B>A 51. (A)
EXERCISE # II
1. (i) a, b ; (ii) a, c ; (iii) b, c, d ; (iv) a, b, c, d, e, f
2. Aromatica, b, d, e, g; Non-aromaticc, f 3. (C) 4. (C) 5. (B)
6. (A)
H NH2 OH
B C C
O O N N N N
7. (a) (b) (c)
H–B B–H NH2–C C–NH2 HO–C C–OH
O N N
8. (D)
9. (i) c > b > a (ii) c > b > a (iii) b > c >a (iv) d > c > b > a (v) c > b > a
(vi) b > c > a (vii) c > b >a (viii) c > a > d > b (ix) b > c > a (x) c > a > b
(xi) c > a > b (xii) a > b > c > d (xiii) b > a > c > d (xiv) d > e > b > a > c
(xv) a > c > b (xvi) b > c > a
81
10. (C) 11. (a) I; (b) I; (c) II; (d) II; 12. (C) 13. (A) 14. (A)
15. (D) 16. (B)
17. (i) a < b (ii) d < a < c < b (iii) b < a (iv) c < b < a (v) c < a < b (vi) a < c < b
(vii) c < b < a (viii) c < b < a (ix) b < a (x) a < c < b < d 18. (A)
19. (D) 20. (B) 21. (D) 22. (a) IV < I < II < III < V (b) III < IV < I < II
23. (B) 24. (A) 25. (a)-I ; (b)-I ; (c)-II
26. (a) 4658 ; (b) 4638 (c) 4632 ; (d) 4650; (e) 5293 27. (A) 28. (B) 29. (D)
30. (i) d > c > b > a ; (ii) e > c > d > b > a; (iii) b > a (iv) a > b (v) b > a ; (vi) a > b
31. (i) a < b ; (ii) e < d < c < b < a ; (iii) a < c < b ; (iv) a > b > c
32. (i) c > b > a ; (ii) a > b > c > d ; (iii) a > b ; (iv) c > b > a
33. a-I; b-I; c-II, d-I 34. Stability order: d > c > b > a ; HOH order: a > b > c > d
35. (C) 36. (D) 37. (B) 38. (C)
39. (i) c > b > a (ii) a > b > c (iii) a > b
EXERCISE # III
1. (C) 2. (A,D) 3. (D) 4. (C) 5. (A,B,D)
6. (A)P,S ; (B)Q,R ; (C)Q,S ; (D)P,S
7. (A)P,Q,S ; (B) R ; (C)P,S ; (D)Q,S
8. (A)R ; (B)S ; (C)P, T ; (D)Q 9. (A)Q,S; (B)-P,S; (C)P,S; (D)R,S
10. (D) 11. (A) 12. (D) 13. (A) l 4. (A) 15. (B) 16. (D)
17. (C) 18. (C) 19. (B) 20. (C) 21. (C) 22. (D) 23. (B)
24. (4) 25. (4)
1. (1) 2. (3) 3. (3) 4. (2) 5. (4) 6. (1) 7. (1)

8. (3) 9. (4) 10. (3) 11. (4) l2. (2) 13. (4) 14. (1)
15. (2)
1. (D) 2. (D) 3. (B) 4. (C) 5. (A) 6. (D) 7. (A)
9. (D) 10. (A) l 1. (D) l 2. (B) 13. (6) 14. (B,C) 15. (A)
16. (6) 17. (9) 18. (5)
82
SOLUTIONS : ELECTRONIC DISPLACEMENT EFFECTS
EXERCISE # I
Note : Check series of –I.
1. Ans. (D)
2. Ans. (C)
3. Ans. (B)
+ – +
4. (A) C–C–C–C–OH (B) C–C–C–C–O–H
E.N. – I
more O – – I
+I
(C) C–C–CH3 (D) –O–CH3
E.N. – I
5. + I effect group
— 
– O, – NH, – COO , – Me `
6. True statement about resonance

(c) Resonance involves delocalization of  electrons only.
C=C–C=C–C=O
(d) Resonance decreases potential energy of an acyclic molecule.
(Due to resonance stability of molecular  in acyclic mol so potential energy)  (mol
cyclic A.B.)
(g) Resonance is not the only way to increase molecular stability.
(+I, H·C also increases stability) (Aromaticity)
(j) The resonance hybrid explains all features of a molecule.
(l) Resonance hybrid is real and resonating structures are imaginary.

(m) Resonance hybrid is always more stable than all canonical structures.
7. Incorrect statement-
Resonating structure are real & have real existence
(Resonating structure is a hypothetical structure which is imaginary)
8. (A) Conjugated alkadiene (CH2 = CH–CH = CH2) (resonance)
83
10. Canonical structure will more stable if
(A) It involves cyclic delocalization of (4n + 2) -electrons than if it involves acyclic
delocalization of (4n + 2) -electrons.
4n + 2 = 6e–
Non aromatic
O O–
|| |
11. CH3 – CH2 – C– CH3 
 CH3 – CH
 C CH3
Its not a resonance phenomena tautomeris-
For resonance 3 parallel P orbital is necessary.
12. (a) (b) N (d)

N H N
l. p localised l. p delocalised l. p delocalised
When l. p is adjacent position of two parallel P-orbital, then l. p is delocalized.

13. CH2 CH
(b)   – CH O (d)
CH2 CH – C  N

(e)
O
l. p localised

14. – NH3
 –I
NH3 NH3

(not possible)
N can't form
S bond
So not involved in resonance only inductive effect.
84
O O
C–NH2 EWG C–NH–CH3 EWG
15. (a) (b)
O O O
C–Cl EWG O–C–CH3 ERG NH–C–CH3 ERG

(c)
O O O
C–OH C–NH–CH3 C–Cl CN
16. (a) (b) (c) (d)
N EWG
(f)
 

17. (b) – N  O CH2 – N = O EWG CH2 – N = O ERG
+ 
(c) –CH = CH2 CH3 – CH2 – CH = CH2 ERG CH3 – CH – CH = CH2 EWG
N = NH N = NH

(f) – N  NH ERG EWG
85
–
O O

18. (a) CH3 – C – CH2 CH3 – C = CH2
–
O O O
 
(b) H – C – CH = CH = CH2 H – C – CH – CH = CH2 H – C = CH – CH = CH2

 
(c) CH2 CH2  CH2 CH2 CH2


(d)
 

 
(e) O O  O O O



(f)  NH N–H NH


(g)  
(h)

O O O

O O O

(i) CH3 – CH = CH – CH = CH – CH – CH3

CH3 – CH = CH – CH – CH = CH – CH3

CH3 – CH – CH = CH – CH = CH – CH3

(j) CH3 – CH = CH – CH = CH – CH2

CH3 – CH = CH – CH – CH = CH2

CH3 – CH – CH = CH – CH = CH2
86
 
19. (a) CH2 – O – CH3 
CH2  O– CH3
Incomplete octet Complete octet
(less stable) (more stable)
(b)
Two benzene structure One benzene ring

(more stable) (less stable)
–
O O
(c) C C –
H CH2 H CH2
Negative charge on more Negative charge on less
E.N. atom is more stable E.N. atom is less stable
– 
O NH O NH
(d) C C
H H H H
Negative charge on Negative charge on
more E.N. atom 'O' less E.N. atom 'N'
(e)
   
CH2 CH2
Aromatic ring

O O
20. (a) H—C C 
OH H O—H
Neutral charged
more stable

(b) O O

Aromatic negative Non-aromatic negative
charge on 'O' charge on 'C'
more stable less stable

(c)
N N

Aromatic
more stable
87
(d)
 
 
CH2 CH2
Aromatic Anti Aroamtic
more stable
 
(e) CH
2 – CH CH – O 
CH2 CH
  – CH O
'Charged structure' 'Neutral'
(f) More EN contain –ve charge and less EN contain +ve charge.
  H.C
OH CH2–CH2 CH2–CH2 CH2
H.C H.C
21. (a) (b) (c) (d)
 Vacant d
CH=CH BH2 Ph–P–Ph
(e) (f) (g)

resen
       
22. (a) CH2 = N = N (b) CH2 – N = N (c) CH2 – N = N (d) CH2 – N  N
Complete Negative charged Positive charged Negative charged
octet on 'C' atom on 'C' on 'C' complete octet
(a > d > c > b)

23. (a) CH3 = CH – C  N CH3 – CH = C = N
Negative charge charge on 'N' (more stable)
on 'C'

O O O O

(b) CH3 – C – CH – C – CH3 CH3 – C = CH – C – CH3
Negative charge on 'C' Negative charge on 'O'
(cross conjugation) extended conjugation
(more stable)
NH2 NH2

(c) CH3 – CH2 – C – NH2 CH3 – CH2 – C = NH2

Incomplete octet Complete octet
(more stable)
88
24.
Neutral positive charge on 'C'

(less stable)
(i > ii > iii > iv)
25. (a) >

O OH
Aromatic compound Extended
(more stable) conjugation
(b) > 
CH2

Aromatic compound Resonance
(c) >
NO2
N
O
Aromatic compound Resonance
(d) >
N O
H
Aromatic
 
N O O
+ +
Positive charge on 'N' Positive charge on 'O'
(more stable) (less stable)
27. (i) >

N N
6 e–/6 atom –
H 6 e /5 atom
Aromatic Aromatic
6 membered 5 membered
89
(ii) CH2 = CH – O – CH = CH2
CH2 = CH – NH – CH = CH2
LP donation tendency N > O
    
(iii) CH2 = CH – NH CH2 – CH = NH < HN = CH – NH HN = CH – NH
Negative charge on 'C' Negative charge on 'N'
(iv) CH2 = CH – F > CH2 = CH – Br
2P 2P 2P 4P
So, electron donatives is for
CH2
(v) > CH2 = CH – CH2
Extended conjugation
(Aromatic ring)
OH
(vi) <
1 Aromatic ring 2 Aromatic ring
 benzene
(vii) >
Benzene Benzene 1 Benzene
36 kal 36 kal
O O
(viii) <
Cross conjugation Extended conjugation
(ix) CH2 = CH – OH < CH2 = CH – CH = CH – OH

less conjugated sys long conjugation
(x) <
Cross Extended conjugation
O O

(xi) CH3 – C – OH < CH3 – C – O Na
equal R.S
 
O O

CH3 – C = O – H CH3 – C = O Na
Resonance
90

(xii) CH2 = CH – O < CH2 = CH – OH
charged neutral
–
COO O–
(xiii) >
Equal R.S
(xiv) >
36 kal 36 kal naphthalene
Two individual 62 kcl
benzene ring
(xv) > CH2 = CH – CH = CH – CH = CH2

Aromatic Resonance

O O

28. (a) CO32– > H–C–O H–C=O
2 equal structure

O O
 C   C
O O O O
3 equal R.S

O
 C 
O O

(b)  < CH2 = CH – CH2 (c) < CH2 = CH – CH = CH2
A. Aromatic Resonance A. Aromatic Resonance
O–H

(d)  > CH2 = CH – CH2 (e) <
Aromatic Resonance
91
29. (A) <
Resonance Aromatic
compound

(B)  >
Resonance A. Aromatic
(C) N < NH2
H
Cross conjugation Extended resonance
NO2
–M
30. Low e– density in the ring
NO2
–M

O
31. + M, + I
CH3 CH3 H
CH3 CH–CH3 CH3–C–CH3 H–C–CH3
32. (i) (ii) (iii) (iv)

3H 1H 0H 2H
H.C H.C
more e– density
+I O –M
33. C–CH3
CH3
H.C
34. CH3 – CH = CH – C – CH3

H.C O +I
Mesomeric
92
35. (i), (ii), (iii)
CH3
CH3 CH3

N
36. (A) C (B) (C) CH3
H H CH3 8  11
9  11
1 1 1
2 2 2
3 3 3
37. 3 R.S of Napthalene 4 4 4
2-1 bond two time double but one time single
O
38. extended conjugated C–O bond length
NH2 NH2 NH3
39. (i) (ii) (iii) (iv) CH2 = NH pure = bond
C–H
O
(iii > ii > i > iv)
More resonance
More = bond character
2 
1 CCH CCH
40.

Resonance
41. Longest bond length CH3 – C = CH2

CH3
6  11
42. CH2 = C = CH2 (pure double bond)
93
43. (A) Benzene (close conjugated)
Two equal R.S all C–C bonds are equal

 
(B) 1, 3-buta.di-ene C = C – C = C C – C = C – C not same length
(C) C–C & C=C are not same length

1 1
2 2
(D) all C–C & C=C are same length
3 3
4 4
Aromatic compound
44. CH3 – CH3 > > CH2 = CH2 > CH  CH

1.39 A 1.39 A
O O
45. CH3 – O – CH = CH – N CH2 = CH – N
+M O O
–M
(I) more resonance (II)
 
CH2 = CH – Cl CH2 – CH = Cl CH2 = CH2 pure double bond
(III)
46. (A,C,D)
47. (a) CH2 = CH2

2 –bond Pure = bond
4H
H.C
Bond angle with  H
(b) CH3 – C  CH CH  CH
 
(c) CH2 = CH CH = CH2 < CH2 = CH CH = CH2
C C
CH2 CH2
94
O O O O
(d) C C (e) C C
NH2 NH2 CH3 NH2 Cl Cl CH3 Cl
3.R.S cross 2.R.S
O O
(f) C C
NH2 NH2 H NH2
48. Bond S
 
(a) CH3 – CH2 – Br   CH – CH – Cl
  3 2  
 
In group top to bottom C–X bond length  so bond strength 
(b)
CH3 – CH = CH – Br > CH3 – CH – CH
Double bond character Br
O
(c) CH3 – C – Cl > CH3 – CH2 – Cl
d.b.c
(d) CH2 = CH – CH = CH2 > CH2 = CH – CH2 – CH3
d.b.c H.C
Due to resonance
CH2 = CH – CH = CH2 < CH2 = CH – NO2

(e)    O
CH2 – CH = CH – CH2 CH2 – CH = N
O
less stable more stable
Due negative charge on 'C'
CH3
(f) <
C2H3 C2H3
9H 6H H.C
95
49. * Remove hydrogen and make radical
1
* Stability 
Bonddissociation energy
1>4>3>2
NH2 NH2 NH2
50. (A) (B) (C) C>B>A

O
more stable so more d.b.c
51. Due to SIR in A Ist compound not participate in resonance.
96
EXERCISE # II
1. (a)  4n + 2 = 10 e– Aromatic n=2
All pheripheri e– count
(b) Total = 6e–

S

(ii) 
6e– 10e–
  
(iii) 6e –
2e– 6e–
N
H
(iv) 10e– Aromatic
H
Si B
H
6e– 6e– Aromatic 6e– Aromatic
B
H–N N–H
(c) Inorganic benzene 6e– Aromatic
H–B B–H
N
H
(f) 10e– Aromatic

N
H
97
2. (a) N 6e– Aromatic Isoxazolc (b) N S 6e– Aromatic
O
H
sp3

(c) Non-Aromatic pyran (d) Aromatic pyryliun ion 6e–
O O
(e) 6e– Aromatic (f) N SP3 Non-Aromatic

O H
NH2
N
–
(g) N O 6e Aromatic cystosine
H
3. (i) (ii) (iii) Not break due to A. N
 
(iv)  Aromatic most stable (v) Aromatic large size ring
 ii > i > iii
4. (i) Anti Aromatic so not break (ii) Anti Aromatic not break
(iii) Aromatic so minimum rotation energy barrier is required
98
5. 
Tub-shab
non-Aromatic non-planar
system
+
6. N
H sp3
H
7. (a) B3H3O3 (Boroxine)

NH2
B
O O
Aromatic
H–B B–H
O
(b) C3N3(NH2)3 (Melamine) (Trimer of cynamide)
N  sp3
N
NH2–C C–NH2
Aromatic
N N
C
NH2
(c) Trimer of isocyanic acid (HN = C = O)3
OH
C
N N
Aromatic
HO–C C–OH
N
 
8. (A) CH3 – CH2 (B) CH3 – CH2 – CH2
3H 2H H.C
H.C
CH3 CH3
 
(C) CH–CH2 (D) CH3 CH–CH2
CH3 CH3
1H 0H
99
CH3
 
9. (i) (C) CH3 – C > CH3 – CH – CH3 > CH3 – CH2
CH3
9H 6H 3H

 
(ii) > >
7H 3H 1H

(iii) 

1H 7H 3H
bca
(iv) Angle strain  S-charactic on ring positive charge is unstable at most E.N. ring
   
> > >

  
(v) (a) CF3  CH2 (b) CCl3  CH2 (c) CBr3  CH2
–I –I –I
– I order – F > – Cl > Br
cba
(vi) (a)  (b) (c)

 
1H +I 2H +I 2H

bca + I effect it distance dependent
  
(vii) (a) HC  C (b) CH2  CH (c) CH3 – CH2
sp sp2 sp3 H.C
cba
   
(viii) (a) (b) (c) (d)
NO2 CH3 Cl
–I +I –I
ca db
100
  
CH2 CH2 CH2
(ix) (a) (b) (c)
N OMe b>c>a
O O
– M, – I + M, – I
  
CH2 CH2 CH2
OH
(x) (a) (b) (c)
OH
+M, –I –I
OH +M, –I
In a and b +H is same but CH3 having more +I in C
ca b
  
CH2 CH2 CH2
CH3
(xi) (a) (b) (c)
CH3
CH3 +I H.C, +I
H.C, +I
ca b
   
CH2 CH2 CH2 CH2
(xii) (a) (b) (c) (d)
CH3 CH2–CH3 CHMe2 CMe3.

H.C = 3  H 2H 1H O
a bcd
Me Ph 

(xiii) (a) Me–C+ (b) Ph–C+ (c) Me – CH2 3  H (d)
Me Ph Highly unstable
9H Resonance
101
(xiv)  In case of d and e resonace is present but in d having more  H.
 Check other by  H
deba c
 
CH2 CH2

(xv) (a) (b) 1H (c) 4H

-resonance
  
(xvi) (a) (b) (c)

Anti Aromatic Aromatic Resonance
highly unstable
bca
   
10. (i) CH3 – O – CH2 > CH3 – CH2 (ii) Me – CH > CH3 – CH2 – CH2
+M H.C Me 2H
6H
   
(iii) CH2 = CH – CH2 > CH3 – CH2 – CH2 (iv) CH2 = CH < CH3 – CH2
Resonance 2H H.C sp2 3H
   
11. (a) (I) CH2 > (II) CH2 = CH – CH2 (b) CH3 – CH2  CH2 
CH
more resonance Resonance

 
CH2 CH2
CH3–CH–CH3 CH3–N–CH3
(c) < (d) (I) <
CH3–C–CH3 CH3–C–CH3
 
H.C Resonance 6H 6  H + (+M of N)



12. (I) (II) (III) (IV)

6H Bridge head 1H 2H

Highly unstable
i  iv  iii  ii
102
13. (carbocation)
CH3 CH3

(A) C (B) CH3–C (C) CH (D) CH2 = CH – CH2
CH3 CH3 Resonance
9H 6H
Resonance
ADBC


14. k(a) CH3O CH2 (b) CH2
+M Resonance
 
(c) CH3 CH2 (d) CH3 – CH2
3H
H.C
a cbd
   
CH2 CH2 CH3 CH2
15.
OH NH2 CH3 C–C–C

C
+M, –I +M, –I H.C O  H, +I
Donation tendency of N > O
ii  i  iii  iv
  
CH2 CH2 CH2
16.
H2–CH CHMe2
CH3 NO2 NO2
H.C –M SIR not in resonance
i  iii  ii
103
 
CH2 CH2
17. (i) (a) < (b)
F NO2
–I –M
   
CH2 CH2 CH2 CH2
(ii) (a) (b) (c) (d)
Cl NO2 CN
–I –M, –I –M, –I
b>c>a>d
 
(iii) (a) CH2 – CH > (b) CH2 – CH3
O +I
Resonance
O O O +I +I
+I
(iv) (a) (b) (c)
 

more resonance Resonance, +I
+I, , stability of anion.
a bc
 

CH2 CH2 CH2
(v) (a) (b) (c)
Cl NO2
–I –M
ba c
 

(vi) (a) (b) (c)

Ant. A Aromatic
Resonance
bca
104
CH2 CH2–CH2
(vii) (a) (b) (c)

Resonance +I Highly unstable
a bc
–I
–I
(viii) (a) (b) (c) –I
Resonance +I Less stable
a bc
(ix) (a) (b)  having more –I

Resonance –I
ab
–I Resonance
(x) (a) CH2 = CH (b) CH2 = CH – CH2 (c) CH2 (d) CH3
sp2 Resonance +I +I
dbca
18. HCC (negative charge is more stable on sp hybridised 'C')

CH2
19. –M, –I group  stability of carbon ion
NO2
–M, –I

20. Aromatic
O
CH3
21. CH2=CH–C > CH2=CH–CH2 > CH3–CH2 > CH2=CH
CH3
Reso + 6  H Resonance 3H
105
  
O O  O
22. (a) +M +M > > > >

O O O
+M +M –I Bridge head
Extended 'C' sp2
O O O O
   
(b) CH2–C–H > CH2–C–CH3 > CH2–C–OH > CH2–C–NCH3
+I +M +M
23. (iv) Ph–C–CH=CH2 i &iv

CH3
24. CH2=CH–CH=CH–CH3 > CH3–CH=C=CH–CH3

Resonance
C
C–C CH3
25. (a) > (b) >
7H 3H
(c) <
2H 4H
26. (a) 1-Heptene (b) 2,4-Dimethyl-l-pentene

CH3 CH3
C=C–C–C–C
C=C–C–C–C–C–C 1 2 3 4 5
7.C, 2  H 7.C, 5  H
(c) 2,4-Dimethyl-2-pentene (d) 4,4-Dimethyl-2-pentene

C C C
C–C=C–C–C C–C=C–C–C
7.C, 7  H C
7.C, 3  H
106
(e) 2,4,4-Trimethyl-2-pentene
C C
HOC  number of 'C'
C–C=C–C–C 8.C 1

C Stability
ea dbc
CH3
27. CH3–C=C–CH3 > CH3–C=CH–CH3 > CH3–C=CH2 > CH3–CH=C
CH3 CH3 CH3 CH3
28. i &iv
29. > > >

Isobuten 2° anion
1° anion
30. Ans. (D > C > B > A)
(i) (a) (b)

8H 9H
Reso + H.C H.C
(c) (d)
4H 2H
(ii) (a) (b)
Reso + H.C 8H H.C
(c) (d)
5H 6H
107
(iii) (a) <
O O
(iv) (a) > Resonance more stable
CH3 H CH3 CH3

(v) (a) C=C < C=C
H CH3 H H
more stable Ci>
CH3 CH3
(vi) CH2=CH–CH > CH2=C
CH3 CH2–CH3
1H more stable 5  H
31. HOH
a bcde
(i) < (ii)
See  H
stable due to
resonance
(iii) (a) (b) (c)

less more stable
bca
(iv) (a) (b) (c) (HOH per benzene ring)

36 Ka R.E 63 Ka R.E K
cba
1
32. H.O.C.  number of 'C' atom 
stable &1
(i) (a) (b) (c)

6.C 7.C 8.C
cba
108
(ii) (a) (b) (c) (d)
(iii) (a) (b) more stable
(iv) (a) > >
33. (a) > (b) >
Resonance stability 3 = bond

(c) CH3–CH = CH–CH3 < CH3–CH2–CH= CH2
6H 2H
(d) >
3H 10  H
34. (a) (b) (c) (d)
stability order resonance extend resonance Benzene aromatic

ring
d  c  b  a H.O.C order a bcd
35. (57)
1-butene C=C–C–C 30 kcal
C=C–C=C 1,3-butation resonance
If two '=' bond mol in resonance than Holt = 2 × 30 = 60 kal
But due to resonance holt is slightly less than 60 kcal
Show
NMe2 sir NH2 SO3H NO2 Br
36.
(A) (B) (C) (D) (E)
109
– –
O +
O O O SIR
+
N N NCr
37. (i) (ii)

resonance not is resonance
(B) C–N (1) < C–N (2)
N=O
5
38. O 1 3
N N=O
less resonance
O Br
When the l.P of Br participates in resonance long conjugation C–S–N and short with C–3 &
Cl–N & C–3–N so bond length of C–1–N & C–3–N are of same length and longer than C.S–N
ssp3
CH3 CH3 CH3
sp 2
Cl
39. (i) (a) (b) (c) r0
Cl
Cl
Direction of dipoles   
a bc (dipole moment angle  dipole moment )
NO2 NO2 NO2

Cl
(ii) (a) (b) (c)
Cl
Cl
Angle  dipole moment  a  b  c
NMe2 NMe2
3
Sp Sp3
(iii) (a) (b) a>b
40. Due to, bridge bound carbon can never be sp2 by brad's rule no real structure possible.
110
EXERCISE # III


1. > R – CH2
Aromatic

2. (i) CH3 – O–

CH3 (ii) CH3–CH2–OH
NO–H–bonding Due to H–bonding intermolecular
(I) (II) (III) (IV)

3. CH3
– CH CH– C  N
sp (more electronegative)
 
CH2 CH2
4.
CH3 CD3
H.C H.C
Strength of C–D/H bond
C–D>C–H
–CH3 has more +H effect than –CD3
O O– O–
5. Acetate ion CH3 – C – O– CH3 – C = O– CH3 – C – O
equal R.S R.H
O O– O–
Formate ion H – C – O– H–C=O H – C – O
R.H C–O equal
NO2 O
6. (A) –M/–R, –I (B) +M, +I
O–CH3 CCH3
(C) +M, –I (D) –M, –I
111
N=O N=O
7. (A) –N = O +M/–I –M/–I

P, Q, S
CH3H.C,+I
(B) –CH3 (R)
O
NH–C–CH3
O
(C) –NH – C – CH3 +M/–I

P, S
CH3 H.C
8. (A)  R +I

NH3 N can't form 5 bond
(B)  S
O–H OH NH2 NH2
(C)  P,T –I –I
(D)  Q
9. (A) Q, S (B) P, S
(C) P, S (D) R, S

4e–
10. – C – O – Et –C–O–C–
O O O
only one side here l.P involved in
resonance fast both side in resonance
a > b (bond length)
112
  
11. CH3 – C – CH3 > C – C > C–C
CH3 C
9H 6H 3
12. 2-butene H3C – C = C – CH3 6H

ethylene CH2 = CH2 less = bond character
pure '=' bond
Hyperconjugation effect , the '=' bond character
 —   
13. CH
 2 CH – Cl 

  CH2 – 
  CH Cl

 CH2 – 
  CH Cl 
–

'Neutral' completeoctet incompleteoctel

(I) (II) (III)
I  II  III
 
CH2 CH2 CH2 CH2 CH2
 
14. (A)

S  R.S
 
(B) CH2 = CH – CH2 CH2 = CH – CH2
A>B

O O

15. CH2 – CH – H CH2 = CH

16. CH3 – C – CH3 9H
CH3 H.C

17.
7H
113
 
18. CH2 = CH < CH3 – CH2
+ve charge 3  H H.C
on '=' bond
+ O +2 O–
19. (I) CH3–N – (II) CH3–N –
O O

20. 10 e– on 'N' not value
N N
H H
(I) (II)
21. Delocalization of electrons  molecular stability CO2 pot energy 


22. (I) Aromatic most stable compound 6e–

(IV) CH3 – CH– CH3
H.C least stable

23. (C6H5) C–Br 
heterolysis
 C
3 ring resonanc with C
O
HO O
24. (a) (b) (c) Azulene (f)
10e– HO O
114
CH3 C
1. CH3 — C — > C — C — > CH3 — CH2 —
CH3
3° 2° 1°
+I effect order
O O–
–
2. H—C—O H—C=O
–1/2
O
–1/2
R.H H — C — O two equal R.S.
3. (i) Acetamide (ii) Acetic acid (iii) Acetonitrile

O O
CH3—C—NH2 CH3—C—OH CH3—C  CN
sp2 sp2 sp3 sp
O
(iv) Acetene CH3—C—CH3
4. CH3 (reactive)
  
5. (C6H5 )3 C  (C6H5 )2 CH  (CH3 )C
Resonance
  
 CH — CH3 CH2
6. CH3 — C — CH3 Cl — C — Cl
CH3 Cl CH3
Vacant-d- +I
+I
+I effect  orbital
resonance
Stability of anion
(equal R.S)
  
CCC 3  C6H5 CH2  (CH3 )2 CH  (CH3 )3 C
7. Non-Aromatic
sp3
115
8. Ortho-nitrophenol p-nitrophenol
OH
OH OH
H-bonding
NO2
NO2 NO2
Less acidic due to intramolecular H-bonding
9.

4e 4e
A.A A.A
H H Cl

10. (i) Cl—C—Cl (ii) H—C—Cl (iii) Cl—C—Cl
 
Cl Cl Cl
 = 0 most symmetrical

CH2
 
11. (I) CH2 = CH – CH2 (II) CH3 – CH2 – CH2 Resonance
resononc H.C.
III > I > II
N
C H H
C O O
=0
12. (1) =0 (2) (3)
C
C O O
N H H
=0 0
H H
S S
(4) 0
=0
S S—H
H
13. Non-Aromatic
116
1. HOH per mole of H2
CH3 C C
(A) C=C–C–C (B) C=C (C) C=C
cis
CH3 Trans
(d) C=C–C=C
C = C resonance stabilized
1
 HOH 
stability
ACBD

CH2
2.  stability

 O–CH3 + M, – I
 
CH3
Cl Cl
Cl
3. (i) (ii) (iii)
9-bond resonance (3  H) Cl
Cl
(iv) =0   D.M. 
Cl
iii  ii  i  iv
4. Because nitrogen can't form five bond.
5. 4ne–
117
6. P-hydroxybenzoic acid O- hydroxybenzoic acid
O
C–OH COOH
OH
(Inter molecular H-bond) (Intra molecular H-bonding)
OH
B.P order inter > intra H-bond
7. (A) CH3Cl (B) CH2Cl2 (C) CHCl3

H H H
H – C – Cl H – C – Cl Cl – C – Cl
H Cl Cl

8.

OH O
H
  
9. CH3 – O–

CH– CH– CH  CH 2
Lp and C repulsion.
10. Adjacent positive like charges unstable

  O
(A)  N
O
+ve and +ve repulsion.
+I 
 
11. (I) O (II) (III) O (IV) 
6  H +M 5H 3  H +M 2H
+M and 2CH3 +I effect
I  III  II  IV
118
        
12. (I) CH 2C N N (B) CH 2 – N  N (C) C H 2– N  N (D) CH2 – N  N
complete octet Incomplete octel complete octet
–ve charge on 'N'
+ve charge on 'C' (For maximum stability)
CH3 
CH2CH3
H
H.C = 6 (6  H)
13.
O

14. Anti aromatic Anti aromatic
H
O–(f)
 H
15. (i) H—C—C
H
H
Vacant P
H ()
O–(f)
H
(ii) H—C—C—C
H
H
NH2 N NH2
16. Melamine N N
NH2
119
17. 9 R.S
OH O
NaOH
+ H2 O

O O O

(1) (2) (3)
O O
 
(6) (4)
 
O O
(7) (5)
 
O O
(8) (9)
18. tub-shape (non-planar) non-aromatic

 4e– 4n = 4 n = 1 Anti-aromatic
sp3

 Aromatic  Non-Aromatic
 
 6e– Aromatic  4e– Anti Aromatic
 6e– Aromatic  Aromatic compound

6e–
 Aromatic
14e–
120
(Organic Chemistry)
EXERCISE - I
Q.1 The compounds 𝐂𝟐 𝐇𝟓 𝐎𝐂𝟐 𝐇𝟓 and 𝐂𝐇𝟑 𝐎𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐇𝟑 are
(A) Chain isomers (B) Position isomers
(C) Metamers (D) Conformational isomers
Q2. The number of primary, secondary and tertiary amines possible with the molecular formula
𝐂𝟑 𝐇𝟗 𝐍 respectively.
(A) 𝟏, 𝟐, 𝟐 (B) 1, 2, 1 (C) 2, 1, 1 (D) 𝟑, 𝟎, 𝟏
Q3. How many benzenoid aromatic isomers shown by 𝐂𝟕 𝐇𝟕 𝐂𝐥?
(A) 4 (B) 3 (C) 5 (D) 6
Q4. Molecular formula 𝐂𝟑 𝐇𝟔 𝐁𝐫𝟐 can have:
(A) Two gem dibromide (B) Three vic dibromide
(C) Two tert. -dibromo alkane (D) Two sec.-dibromo alkane
Q5. Following compounds are:
(A) Position isomer (B) Chain isomer

(C) Metamers (D) Functional isomer
Q6. Which of the following is incorrect relation:
(A) identical
(B) positional isomers
(C) positional isomers
(D) homologues
APNI KAKSHA 6
(Organic Chemistry)
Q7. Select whether given realationship is true or false?
functional isomer
metamers
metamers
functional isomers
(A) TFTF (B) FTTF (C) TTFT (D) TFFT
Q8. Following compounds are:
(A) Functional isomer (B) Chain isomer

(C) Metamer (D) Position isomer
Q9. The type of isomerism observed in urea molecule is
(A) Chain (B) Position (C) Metamers (D) Functional

Q10. How many minimum no. of 𝐂-atoms are required for position isomer in alkene?
(A) 6 (B) 4 (C) 3 (D) 5
Q.11 Which of the following cannot be written in an isomeric form?

(A) 𝐂𝐇𝟑 − 𝐂𝐇(𝐎𝐇) − 𝐂𝐇𝟐 − 𝐂𝐇𝟑 (B) 𝐂𝐇𝟑 − 𝐂𝐇𝐎
(C) 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐥 (D) 𝐂𝐥 − 𝐂𝐇𝟐 𝐂𝐇𝟐 − 𝐂𝐥
APNI KAKSHA 7
(Organic Chemistry)
Q12. Given compound shows which type of isomerism
(A) Chain isomerism (B) Positional isomerism

(C) Metamerism (D) Functional group isomerism
Q.13 Which of the following involves Diad system for prototropy:
(A) 𝐂𝐇𝟑 𝐂𝐎𝐂𝐇𝟑 (B) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐍𝐎𝟐 (C) (D) HCN
Q.14 How many structural isomers of 𝐂𝟓 𝐇𝟏𝟎 are possible.

(A) 10 (B) 11 (C) 12 (D) 13
Q.15 The number of isomers of dibromoderivative of an alkene (molar mass 𝟏𝟖𝟔 𝐠 𝐦𝐨𝐥−𝟏 ) is
(A) 2 (B) 3 (C) 4 (D) 6
Q.16 How many structural isomeric primary amines are possible for the formula 𝐂𝟒 𝐇𝟏𝟏 𝐍?
(A) 2 (B) 3 (C) 4 (D) 5
Q.17 For the given compound, choose the incorrect option?
(A) On treatment with 𝐍𝐚𝐎𝐃/𝐃𝟐 𝐎 for long time, it has 7 deuterium in its enol form
(B) It has all types of permanent electronic displacement effect present.
(C) It has IUPAC name "Pent-2-en-4-one."
(D)None of the above.
Q.18 Among the following the compounds having the highest enol content:
(A) 𝐂𝐇𝟑 𝐂𝐇𝐎 (B) 𝐂𝐇𝟑 𝐂𝐎𝐂𝐇𝟑
(C) (D) 𝐂𝐇𝟑 − 𝐂𝐎 − 𝐂𝐇𝟐 − 𝐂𝐎𝟐 𝐂𝐇𝟑
Q.19 Given interconversion takes place in
(A) Acidic medium (B) Basic medium (C) Both (D) None
APNI KAKSHA 8
(Organic Chemistry)
Q.20 (I) isomerizes to (II) on addition on small amount of base then structure of (II) is
(A) (B)
(C) (D)
Q.21 Major product (𝐏) obtained is:
(A) (B)
(C) (D)
Q.22 Decreasing order of enol content of the following compounds in liquid phase is:
(A) 𝟐 > 𝟏 > 𝟑 > 𝟒 (B) 𝟏 > 𝟐 > 𝟑 > 𝟒 (C) 𝟒 > 𝟑 > 𝟐 > 𝟏 (D) 𝟑 > 𝟏 > 𝟐 > 𝟒
Q.23 Decreasing order of enol content of the following compound in liquid phase
(a) (b)
(c) (d)
(A) a > b > c > d (B) c > b > a > d (C) c > b > d > a (D) b > c > a > d
APNI KAKSHA 9
(Organic Chemistry)
Q.24 What is the correct IUPAC name of the following compound
(A) 2E, 4E, 6Z 4-methyl octa-2, 4, 6 triene (B) 2E, 4Z, 6Z 5-methyl octa-2, 4, 6 triene
(C) 2Z, 4Z, 6Z 5-methyl octa-2, 4, 6 triene (D) 𝟐𝐄, 𝟒𝐙, 𝟔𝐄 4-methyl octa-2, 4, 6 triene
Q.25 The IUPAC name of the given compound is
(A) 2, 4-di[(E)-ethylidene] cyclobutene (B) 1,3-di-[(E)-ethylidene] cyclobutane

(C) 1, 4-di-E-ethyldenecyclobutane (D) (E)-1, 4-diethylidenecyclobutane
APNI KAKSHA 10
(Organic Chemistry)
EXERCISE - II
Q1. The IUPAC name of the compound is:
(A) (2E, 4E, 6Z)-octa-2,4,6-triene (B) (2E, 4E, 6E)-octa-2,4,6-triene

(C) (𝟐𝐙, 𝟒𝐄, 𝟔𝐙)-octa-2,4,6-triene (D) (2Z, 4Z, 6Z)-octa-2,4,6-triene
Q2. Which of the following statements is (are) not correct?
(A) Metamerism belongs to the category of structural isomerism

(B) Tautomeric structures are the resonating structures of a molecule
(C) Keto form is always more stable than the enol form
(D) Both B and C

Q3. Which compound can show tautomerism:
(A) (B) (C) (D) Acetyl acetone
Q4. Tautomerism form of this compound is(are):
(A) (B)
(C) (D)
APNI KAKSHA 11
(Organic Chemistry)
Q5. Which of the following is not the correct relationship
(A) II & IV are metamer (B) I & II are functional isomer

(C) I & III are chain isomer (D) I and IV are positional isomer
Q6. Which of the following compounds have higher enolic content than Keto content:
(A) (B)
(C) (D)
Q7. In which of the following pairs first will have higher enol content than second:
(A) and
(B) and
(C) and
(D) and
APNI KAKSHA 12
(Organic Chemistry)
Q8. Among these tautomers, correct stability order is:
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I
Q9. Most stable tautomer of following compound is:
(A) (B)
(C) (D)
Q10. Which of the following can show tautomerise.
(A) (B)
(C) (D)
Q11. What is relation between (I), (II) and (III)?
(A) I and II are tautomers

(B) III is conjugate base of II
(C) III is resonance structure of I
(D) no relation exists
Q12. The isomerism observed in cyclo alkanes is(are):
(A) metamerism (B) chain isomerism
(C) position isomerism (D) Both B and C
APNI KAKSHA 13
(Organic Chemistry)
Q13. Only two isomeric monochloro derivatives structure are possible for:
(A) n-butane (B) 2, 4-dimethyl pentane
(C) benzene (D) 2-methyl propane
Q14. An organic compound with molecular formula 𝐂𝟐 𝐇𝟓 𝐍𝐎 contains doubly linked atoms. It can
shows:
(A) chain isomerism (B) Functional Isomerism
(C) tautomerism (D) positional isomerism
Q15. Which of the following can exist in 'syn' and 'anti' form?
(A) 𝐂𝐇𝟑 − 𝐍 = 𝐍 − 𝐎𝐇
(B) 𝐂𝐇𝟑 − 𝐍 = 𝐍 − 𝐂𝐇𝟑
(C) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐍 − 𝐎𝐇
(D) (𝐂𝐇𝟑 )𝐂 = 𝐍 − 𝐎𝐇
Q16. The Z-isomer among the following are:
(A) (B)
(C) (D)
Q17. Which of the following is/are correct matchings?
(A) and − Metamers
(B) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂 ≡ 𝐂𝐇 and 𝐂𝐇𝟑 − 𝐂 ≡ 𝐂 − 𝐂𝐇𝟑 − Position iso

(C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐍𝐇𝟐 and − Tautomers
(D) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐎𝐇 and (𝐂𝐇𝟑 )𝟐 𝐎 − Functional isomer

Q18. Which of the following compounds can show tautomerism?
(A) (B)
(C) (D)
APNI KAKSHA 14
(Organic Chemistry)
Q19. Which of the following has (have) more number of stable conformations than ethyl chloride?
(A) Butane (B) Isopropanol
(C) n-pentane (D) Neohexane
Q20. Statement-1 : E-cyclodecene is having more 𝚫𝐇𝐂 (Heat of combustion) than 𝐙 isomer.
Statement-2 : E-cyclodecene is more stable than 𝐙 isomer.
(A) Statement- 1 is true, statement- 2 is true and statement- 2 is correct explanation for
statement- 1 .
(B) Statement- 1 is true, statement- 2 is true and statement- 2 is NOT the correct explanation
for statement-1.
(C) Statement- 1 is true, statement- 2 is false.
(D) Statement- 1 is false, statement- 2 is true.
Q21. Match the Column I with Column II:
Column I (Pair) Column II (Relation)
(A) (P) Chain isomer
(B) (Q) Positional isomer
(C) (R) Metamers
(D) (S) Tautomers
Q22. Match the column :
Column I Column II
(A) (P) Tautomers
(B) (Q) Structural isomers
APNI KAKSHA 15
(Organic Chemistry)
(C) (R) Position isomers
(D) (S) Atleast one of the two
structures is enol
APNI KAKSHA 16
(Organic Chemistry)
EXERCISE - III
Q1. How many benzenoid isomer are possible for molecular formula of cresol?
Q2. Find out the total number of cyclic structural isomers of 𝐂𝟔 𝐇𝟏𝟐 .
Q3. Calculate the number of Benzenoid isomers possible for 𝐂𝟔 𝐇𝟑 𝐂𝐥𝐁𝐫𝐈.
Q4. Calculate the total number of structural isomers of 𝟑∘ -amines for the molecular formula 𝐂𝟔 𝐇𝟏𝟓 𝐍
are?
Q5. How many cyclopentane structural isomers are possible for 𝐂𝟕 𝐇𝟏𝟒 .
Q6. Mention the specific type of isomerism exhibited by each of the following pairs:
(a) 1,2-dichloro ethane and 1,1-dichloro ethane (b) Propanoic acid and methyl acetate
(c) Methyl acetate and ethyl formate (d) o-Nitrophenol and P-nitrophenol
(e) Anisole and o-cresol (f) Phenol and Cyclohexa-2,4-dien-1-one
Q7. In each of the following pairs which is more stable:
(A)
(B)
(C)
(D)
(E)
APNI KAKSHA 17
(Organic Chemistry)
Q8. In each of the following pairs which is more stable:
(A)
(B)
(C)
(D)
(E)
Q9. In each of the following pairs which will have less enol content:
(A) and (B) and
(C) and (D) and
(E)
APNI KAKSHA 18
(Organic Chemistry)
Q10. In each of the following pairs which will have less enol content:
(A) and
(B) and
Q11. In each of the following sets of compounds write the decreasing order of % enol content.
(A)
(B)
(A)
(B)
Q14.
Among these give ease of enolization.

APNI KAKSHA 19
(Organic Chemistry)
Q15. % enol content of acetylacetone in following solvents is found as:

Solvent % enol content
𝐇𝟐 𝐎 𝟏𝟓
Liquid state 𝟕𝟔
hexane 𝟗𝟐
gas phase 𝟗𝟐
Explain the observation.
Q16.
Explain the observation.

Q17. Decreasing order of enol content of the following. (along with proper explanation).
(A)
(B)
(C)
(D)
(E)
Q18.
(A), (B) and (C) are structural isomers and isomerization is effectively carried out by trace of
base. Give structure of (B) and (C) and also write base catalysed mechanism for this
interconversion.
Q19. Calculate the total number of open chain isomeric carbonyl compounds of molecular formula
𝐂𝟓 𝐇 𝟖 𝐎 .
APNI KAKSHA 20
(Organic Chemistry)
ANSWER KEY
EXERCISE – I
1. (C) 2. (C) 3. (A) 4. (A) 5. (A) 6. (B) 7. (C)
8. (C) 9. (D) 10. (B) 11. (C) 12. (C) 13. (D) 14. (A)
15. (B) 16. (C) 17. (C) 18. (C) 19. (C) 20. (C) 21. (C)
22. (B) 23. (B) 24. (D) 25. (B)
EXERCISE – II
1. (C) 2. (D) 3. (A, C, D) 4. (A, B, D) 5. (A, D)
6. (B, D) 7. (A, C) 8. (C) 9. (A) 10. (A, B, C)
11. (A) 12. (D) 13. (A, D) 14. (C) 15. (C)
16. (A, C) 17. (B, D) 18. (A, B, C, D) 19. (A, B, C) 20. (C)
21. (A) R, (B) Q, (C) S, (D) Q
22. (A) P, Q, S (B) Q, S (C) Q, R, S, (D) Q, S
EXERCISE – III
1. (5) 2. (12) 3. (10) 4. (7) 5. (4)
6. (a) Positional (b) Functional (c) Metamerism (d) Positional (e) Functional
(f) Tautomerim
7. (a) 2; (b) 2; (c) 1; (d) 1; (e) 1
8. (a) 2; (b) 2; (c) 1; (d) 2; (e) 1 9. (a) 2; (b) 1; (c) 2; (d) 1; (e) 2
10. (a) 2; (b) 2 11. (a) 3>1>2; (b) 4>2>1>3;
12. (i) 4 > 1 > 3 > 2; (ii) 3 > 1 > 4 > 2 13. 3>4>2>1
14. 3>1>2
17.
(a) Tightly on stableketo due to repulsion between 𝛂 − 𝐂𝐎 groups has 𝟏𝟎𝟎% enol.
(b) Active ' 𝐇 ' atom / Acidic 'H' atom so has more enolic content (enol stabilise by resonance &
Intra molecular 𝐇-bonding)
(c) Enolic contents decreases with introduction of 𝐞− donator group which causes repulsion in
enolic form.
APNI KAKSHA 21
(Organic Chemistry)
(d) Due to ester group acidic structure of active 𝐇 decreases &𝐂 = 𝐂 of enol undergoese cross
resonance.
(e) Lowest enolic content because is more stable than Bond
18.
19. (8)
APNI KAKSHA 22
(Chemistry) STEREOISOMERISM
EXERCISE – I
Q1. Compound CH2 Cl2 contain :
(A) Plane of symmetry (B) Centre of symmetry
(C) Axis of symmetry (D) Both (A)&(C)
Q2. If ' X ' is total number of plane of symmetry, ' Y ' is total number of two fold axis of symmetry and
' Z ' is total number of four fold alternate axis of symmetry present in CH4 . Then find the value of
(X + Y − Z).
(A) 3 (B) 4 (C) 5 (D) 6
Q3. How many stereoisomers of the following molecule are possible?
HOOC. CH = C = CH. COOH
(A) Two optical isomers
(B) Two geometrical isomers
(C) Two optical and two geometrical isomers
(D) None
Q4. The number of cis-trans isomer possible for the following compound.
(A) 2 (B) 4 (C) 6 (D) 8
Q5. has ' x ' chiral centre then find the value of x :
(A) 7 (B) 8 (C) 6 (D) 5

Q6. The number of optically active compounds in the isomers of C4 H9 Br is.
(A) 1 (B) 2 (C) 3 (D) 4
Q7. Compound have
(A) Plane of symmetry (B) Centre of symmetry

(C) Axis of symmetry (D) None
APNI KAKSHA 12
Q8.
Configuration of compound is :
(A) 2 S, 3 S (B) 2R, 3 S
(C) 2R, 3R (D) 2S, 3R
Q9. Which of the given conformation of n-butane is chiral ?
(A) Fully Eclipsed (B) Anti
(C) Gauche (D) None of these
Q10. Minimum molecular weight of a hydrocarbon containing minimum number of C-atom to show
optical isomerism.
(A) 100 (B) 80
(C) 68 (D) 70
Q.11 Compounds which can show both optical as well as geometrical isomerism:
(A) (B)
(C) (D)
Q12. Which of the following will not show optical isomerism:
(A) (B)
(C) (D)
Q13. Optical & geometrical isomerism both can be shown by
(A) (B)
(C) (D)
APNI KAKSHA 13
Q14. Which of the following will not show optical isomerism.
(A) Cl − CH = C = C = CH − Cl (B) Cl − CH = C = C = C = CH − Cl
(C) (D)
Q15. Meso-tartaric acid and d-tartaric acid are :

(A) Positional isomers (B) Enantiomers
(C) Diastereomers (D) Racemic mixture
Q16. The two compounds given below are :
(A) Enantiomers (B) Diastereomers

(C) Optically inactive (D) Identical
Q17. Which of the following combinations amongst the four Fischer projections represents the same
absolute configurations?
(A) (II) and (III) (B) (I) and (IV)

(C) (II) and (IV) (D) (III) and (IV)
Q18. The S-ibuprofen is responsible for its pain relveing property. Which one of the structure shown
is S-ibuprofen :
(A) (B)
(C) (D)
APNI KAKSHA 14
Q19. Which of the following is a 'threo' isomer :
(A) (B)
(C) (D)
Q20. Number of possible stereoisomers of glucose are:

(A) 10 (B) 8 (C) 16 (D) 20
Q.21 Which of the following is not D sugar :
(A) (B)
(C) (D)
Q22. Number of chiral centres in [X] & [Y] is a & b respectively. The value of (a–b) is
(A) 1 (B) 2 (C) 3 (D) 4

Q23. For the newman projection of n-butane, which of the following pair(s) of (X,Y) is/are possible?
(A) (CH3 , CH3 ) (B) (CH3 , Et) (C) (H, Et) (D) (Et, H)
APNI KAKSHA 15
Q24. How many stereoisomers can exist for the following acid.
(A) Two (B) Four (C) Eight (D) Six

Q25. Incorrect relationship between given compounds are
(A) Both are geometrical isomers (B) Both are stereo isomers
(C) Both are enantiomers (D) Both are diastereomers
Q26. Identify meso compound.
(A) (B)
(C) (D)
Q27. A pure sample of 2-chlorobutane shows rotation of PPL by 30∘ in standard conditions. When
above sample is made impure by mixing its opposite form, so that the composition of the mixture
becomes 87.5% d-form and 12.5%l-form, then what will be the observed rotation for mixture.
(A) −22.5∘ (B) +22.5∘
(C) + 7.5∘ (D) −7.5∘
Q28. When an optically active compound is placed in a 10dm tube is present 20gm in a 200ml solution
rotates the PPL by 30∘ . Calculate the angle of rotation & specific angle of rotation if above solution
is diluted to 1 Litre.
(A) 16∘ &36∘ (B) 6∘ &30∘
(C) 3∘ &30∘ (D) 6∘ &36∘
Q29. Identify % optical purity if 6gm(+) − 2-butanol is mixed with 2gm(−) − 2-butanol.
(A) 50% (B) 66.6%
(C) 33.3% (D) 75%
APNI KAKSHA 16
Q30. A mixture of d and 1, 2-bromobutane contain 75% d-2-bromobutane. Calculate enantiomeric
excess.
(A) 75% (B) 25% (C) 50% (D) 100%
Q31. Which of the following is example of meso compound?
(A) (B)
(C) (D)
Q32. Which of the following has C2 &C3 axis of symmetry?
(A) (B) H2 CCl2
(C) H3 C − Cl (D)
Q33. Which of the following pair of cyclohexane is flexible?

(A) Chair (B) Twist boat
(C) Half boat (D) All of these
Q34. Compound related as :
(A) Enantiomers (B) Conformation

(C) Identical (D) Diastereomers
Q35. For the given configuration :
Which of the compound/configuration are optically active :

(A) I (B) II (C) III (D) IV
APNI KAKSHA 17
EXERCISE – II
(JEE Advanced Oriented Level-II)
Q1. Molecular formula C5 H10 O can have :
(A) 6-Aldehyde, 4-Ketone
(B) 5-Aldehyde, 3-Ketone
(C) 4-Aldehyde, 3-Ketone
(D) 5-Aldehyde, 2 -Ketone
Q2. Statement 1: is a chiral resolvable molecule.
Statement 2: Et is non-superimposable on its mirror image.
(A) Statement- -1 is true, Statement- 2 is true; Statement -2 is not the correct explanation of
Statement -1
(B) Statement-1 is true, Statement-2 is true ; Statement-2 is the correct explanation of
Statement-1
(C) Statement-1 is true, Statement-2 is false
(D) Statement- 1 is false, Statement- 2 is true
Q3. Total number of stereoisomer of following compounds are respectively
CH3 − CH = CH − CH(OH) − CH = CH − CH3 ; CH3 − CH(OH) − CH = CH − CH(OH) − CH3
(A) 4,6 (B) 8 (C) 6,6 (D) 8,8
Q4. Which of the following compounds are optically active?
(A) CH3 − CH(OH) − CH2 − CH3
(B) H2 C = CH − CH2 − CH = CH2
(C)
(D)
APNI KAKSHA 18
Q5. Which out the following are Non-resolvable :
(A)
(B)
(C)
(D)
Q6. Which of the following statements is/are not correct:

(A) Metamerism belongs to the category of structural isomerism
(B) Tautomeric structures are the resonating structures of a molecule
(C) Keto form is always more stable than the enol form
(D) Geometrical isomerism is shown only by alkenes
Q7. Identify compounds which are not meso:
(A) (B)
(C) (D)
Q8. Which of the following statements for a meso compound is/are correct :
(A)The meso compound has either a plane or centre of symmetry or both
(B)The meso compound is optically inactive due to internal compensation.
(C)The meso compound is achiral
(D)The meso compound is formed when equal amounts of two enantiomers are mixed
APNI KAKSHA 19
Q9. Compound A having molecular formula C2 Cl2 Br2 . A having plane of symmetry ( POS), centre of
symmetry (COS)&C2 axis of symmetry, A is :
(A) (B)
(C) (D)
Q10. Among the following the non- resolvable compound is/are :
(A) (B)
(C) (D)
Q.11 Compound is/are ?
(A) (2R, 3S), L

(B) L, Erythreo
(C) Threo , D
(D) (2R, 3S), D
Q12. Relation between compounds are :
(A) I & II = Enantiomers

(B) II & III = Enantiomers
(C)I & II = Identical
(D) II & III = Identical
APNI KAKSHA 20
Q13. Compare the stability of following conformations of 1,4-Dimethyl cyclohexane :
(A) P = Q > R (B) P > Q > R (C) Q > P > R (D) R > P = Q
Q14. Identify correct relation between pair of compounds ?
(A) Diastereomers
(B) Identical
(C) Diastereomers
(D) Enantiomers
Q15. Column-I Column-II
(A) (P) Structural
(B) (Q) Identical
APNI KAKSHA 21
(C) (R) Enantiomers
(D) (S) Diastereomers
(A) (P) Geometrical isomers
(B) (Q) At least one of the
compound can show

Geometrical Isomerism
(C) (R) At least one of the

compound can show
Optical Isomerism
(D) CH2 = CH − CH = CH − CH3 CH3 − CH = C = CH − CH3 (S) Positional isomers
(A) A pair of metamer (P)
(B) Tautomerism (Q) CH3 OC3 H7 ; C2 H5 OC2 H5
(C) A pair of geometrical isomer (R)
(D) A pair of diastereomers (S)
(E) A pair of optical isomer CH3 ⋅ CH2 ⋅ CH = CH − OH

(T)
APNI KAKSHA 22
Subjective Type Questions:
Q18. What is number of chiral centres present in Diosgenen is :
Q19. Calculate the total number of chiral carbon atoms in.
(i) (ii)
Q.20 Total number of isomers of bromochlorofluoroiodo propadiene is ?
Q.21 Find out the total number of cyclic isomers of C6 H12 which are optically active?
Q22. How many of the given compounds are chiral :
(i) (ii) (iii) (iv)
(v) (vi) (vii)
(viii) (ix)
Q23. With reasons, state whether each of the following compounds I to VIII is chiral
(i) (ii) (iii)
(iv) (v) (vi) (vii)
APNI KAKSHA 23
Q24. How many cyclopentane structures (including stereo) are possible for C7 H14 .
Q25. The number of diastereoisomers (excluding optical) for 1-bromo-2-chloro-3-iodocyclopropane.
Q26. Identify total number of stereoisomers for the following compound :
Q27. How many of the given molecule / species are chiral :
(i) (ii) (iii)
(iv) (v) (vi)
(vii) (viii) (ix) CH4

Q28. For the compound '5-Methyl hept-3-en-2-one' if :
(i) Total number of stereoisomers possible is ' x '
(ii) Total number of enantiomeric pairs possible is ' y ' Then represent your answer as 'xyx'
[For example x = 1, y = 2 then answer is 121]
Q29. How many of following has same number of stable conformation?
(1) Ethane (2) Propane (3) Butane
(4) Isobutane (5) Neopentane (6) Neohexane
(7) Methanol (8) Dimethylether (9) Ethyl Chloride
Q30. How many of following has only three stable conformation?
(1) 2,2-dimethylbutane (2) isopropanol (3) 2-chlorobutane
(4) Pentane (5) (+) 2,3-Dibromobutane (6) Ethanol
APNI KAKSHA 24
EXERCISE – III
(JEE ADVANCE ORIENTED LEVEL-II)
Q1. Observe the given compounds and answer the following questions.
(i) Which of the above formulae represent identical compounds ?

(A) I and II (B) I and IV (C) II and IV (D) III and IV
(ii) Which of the above compounds are enantiomers ?
(A) II and III (B) III and IV (C) III and V (D) I and V
Q2. Which of the following option is correct regarding the given compounds :
(A) Both are identical (B) Both are optically inactive

(C) Both are optically active (D) Geometrical isomer
Q3. Which of the following pairs of compound is/are identical ?
(A) (B)
(C) (D)
Multiple Correct Type:

Q4. Which of the following statements is/are not correct for D-(+) glyceraldehyde :
(A) The symbol D indicates the dextrorotatory nature of the compound
(B) The sign(+) indicates the dextrorotatory nature of the compound
(C) The symbol D indicates that hydrogen atom lies left to the chiral centre in the Fischer
projection diagram
(D) The symbol D indicates that hydrogen atom lies right to the chiral centre in the Fischer
projection diagram
APNI KAKSHA 25
Q5. Which of the following are correct representation of L-amino acids :
(A) (B)
(C) (D)
Q6. Identify relation between these two compounds :
(A) Homomers (B) Enantiomers

(C) Diastereomers (D) Positional Isomers
Comprehension Type:
Paragraph for Q.No. 7 to 8
Four compounds are given below 'S' is a stereoisomer of P.
(P) (Q)
(R) (S)
Q7. P & Q are related as :

(A) Identical (B) Enantiomer
(C) Diastereomer (D) Positional isomerism
Q8. If Q and S are enantiomer then which is/are correctly matched :
(A) X=H (B) Y=Cl (C) Z=Et (D) X=Cl
APNI KAKSHA 26
Paragraph for Q. No. 9 to 11
S(+) Mono sodium Glutamate (MSG) is a flavour enhancer used in many foods. Fast foods often
contain substantial amount of MSG and is widely used in Chinese food. If one mole of above MSG
was placed in 845ml solution and passed through 200 mm tube, the observed rotation was found
to be + 9.6∘
Q9. Find out the specific rotation of (–) MSG:

(A) + 24°
(B) +56.8º
(C) –48°
(D) None of these
Q10. Find out the approximate percentage composition of (−) MSG in a mixture containing (+) MSG
and (-) MSG whose specific optical rotation is −20∘ :
(A) 83.3%
(B) 16.7%
(C) 91.6%
(D) 74%
Q.11 If 33.8 g of (+) MSG was put in 338ml solution and was mixed with 16.9 g of (−) MSG put in
169ml solution and the final solution was passed through 400 mm tube. Find out observed
rotation of the final solution:
(A) +1.6∘
(B) +4.8∘
(C) +3.2∘
(D) None of these
Among the following structures?
(I) (II) (III)
APNI KAKSHA 27
(IV) (V) (VI)
(VII) (VIII)
Q12. Among the following structures?
(A) III (B) IV (C) V (D) VII
Q13. Which of the following will not show optical isomerism
(A) I (B) II (C) V (D) VIII
Q14. Matrix Match Typed
Column-I Column-II
(Compounds) (Relation)
(A) (P) Metamers
(B) (Q) Functional Isomer
(C) (R) Geometrical isomer
(D) (S) Enantiomer
(T) Diastereomer
APNI KAKSHA 28
Q15. Match List-I, II, III with each other :
List-I List-II List-III
(A) (1) (i) (2R, 3R)
(B) (2) (ii) (2S,3S)
(C) (3) (iii) (2S,3R)
(D) (4) (iv) (2R,3S)

Subjective Type:
Q16. In what stereoisomeric forms would you expect the following compounds to exist ?
(A) EtCH(CO2 H)Me (B) MeCH(CO2 Et)CO2 H
(C) (D)
(E) (F) Et (Me) C = C = C (Me)Et
(G) (H)
(i) (j)
(k)
APNI KAKSHA 29
Q17. Calculate the number of Benzenoid isomers possible for C6 H3 ClBrI.
Q18. What are the relationships between the following pairs of isomers ?
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)
Q19.
Find out total number of structures of X.
APNI KAKSHA 30
Q20. Calculate the number of chiral center in the molecule Ethyl 2,2-dibromo-4-ethyl-6-methoxy
cyclohexane carboxylate.
Q21. Calculate the total number of stereoisomers possible for
(i) (ii)
(iii) (iv)
(v) (vi)
(vii)
(viii) (ix)
(x) (xi)
Q22. Find the total number of stable conformation having non zero dipole moment for meso-2,3-
dichloro butane
APNI KAKSHA 31
EXERCISE-IV (A) (JEE MAINS)
Q1. Recemic mixture is formed by mixing two : [AIEEE-2002]
(A) Isomeric compounds (B) Chiral compounds
(C) Meso compounds (D) Enantiomers with chiral carbon
Q2. Following types of compounds I and II [AIEEE-2002]
(I) CH3 CH = CHCH3
(II) are studied in terms of isomerism in
(A) Chain isomerism (B) Position isomerism

(C) Conformers (D) Stereo isomerism
Q3. Among the following four structures I to IV [AIEEE-2003]
It is true that
(A) All four are chiral compounds (B) Only I and II are chiral compounds
(C) Only III is a chiral compound (D) Only II and IV are chiral compounds
Q4. Which of the following will have a meso-isomer also [AIEEE-2004]
(A) 2-chlorobutane (B) 2,3-dichlorobutane
(C) 2,3-dichloropentene (D) 2-hydroxy propanoic acid
Q5. Amongst the following compounds, the optically active alkane having lowest molecular mass is
(A) CH3 − CH2 − C = CH (B)
(C) (D) CH3 − CH2 − CH2 − CH3
Q6. Which of following compounds is not chiral [AIEEE-2005]

(A) 1-chloropentane (B) 2-chloropentane
(C) 1-chloro-2-methyl pentane (D) 3-chloro-2-methyl pentane
Q7. Of the five isomeric hexanes, the isomer which can give two monochlorinated compounds is:
[AIEEE-2005]
(A) 2-methyl pentane (B) 2,2-dimethyl butane
(C) 2,3-dimethyl butane (D) n-hexane
APNI KAKSHA 32
Q8. Which types of isomerism is shown by 2,3-dichloro butane [AIEEE-2005]
(A) Structural (B) Geometric (C) Optical (D) Diastereo
Q9. The absolute configuration of is: [AIEEE-2008]
(A) S, S (B) R, R (C) R, S (D) S, R

Q10. The number of stereoisomers possible for a compound of the molecular formula CH3 − CH =
CH − CH(OH) − Me is [AIEEE-2009]
(A) 4 (B) 6 (C) 3 (D) 2
Q11. Out of the following, the alkene that exhibits optical isomerism is : [AIEEE-2010]
(A) 2-methyl-2-pentene (B) 3-methyl-2-pentene
(C) 4-methyl-1-pentene (D) 3-methyl-1-pentene
Q12. The optically inactive compound from the following is : [JEE-MAIN 2015]
(A) 2-chloropropanal (B) 2-chlorobutane
(C) 2-chloro-2-methylbutane (D) 2-chloropentane
Q13. The absolute configuration of : [JEE-MAIN 2016]
(A) (2R, 3R) (B) (2R, 3S) (C) (2S, 3R) (D) (2S, 3S)
Q14. Which of these factors does not govern the stability of a conformation in acyclic compounds ?
[JEE MAIN-2019]
(A) Steric interactions (B) Torsional strain
(C) Electrostatic forces of interaction (D) Angle strain
Q15. In the following skew conformation of ethane, H ′ − C − C − H ′ " dihedral angle is:
[JEE MAIN-2019]
(A) 58º (B) 151º (C) 120º (D) 149º
APNI KAKSHA 33
Q16. Which of the following compounds will show the maximum 'enol' content?
[JEE MAIN-2019]
(A) CH3 COCH2 COCH3 (B) CH3 COCH3
(C) CH3 COCH2 COOC2 H5 (D) CH3 COCH2 CONH2
Q17. Number of chiral centers in chloramphenicol is : [JEE MAIN-2020]
Q.18 The total number of monohalogenated organic products in the following (including
stereoisomers) reaction is [JEE MAIN-2020]
A
(i) H2 /Ni/Δ
(ii) X2 /Δ
(Simplest optically
active alkene)
APNI KAKSHA 34
EXERCISE-IV
(B) (JEE Advanced)
Q1. The shows: [IIT JEE - 1995]
(A) Geometrical isomerism (B) Optical isomerism

(C) Geometrical & optical isomerism (D) tautomerism
Q2. How many optically active stereoisomers are possible for butane -2,3-diol:
[IIT JEE - 1997]
(A) 1 (B) 2 (C) 3 (D) 4
Q3. The number of possible enantiomeric pairs that can be produced during monochlorination of
2 -methyl butane is : [IIT JEE - 1997]
(A) 2 (B) 3 (C) 4 (D) 1
Q4. Identify the pairs of enantiomers and diastereomers from the following compounds I, II and III
[IIT JEE - 2000]
Q5. Which of the following compounds exhibits stereoisomerism [IIT JEE - 2002]
(A) 2-Methylbutene-1 (B) 3-Methylbutyne-1
(C) 3-Methylbutanoic acid (D) 2-Methylbutanoic acid
Q6. On monochlorination of 2-methylbutane, the total number of chiral compounds formed is :
[IIT JEE - 2004]
(A) 2 (B) 4 (C) 6 (D) 8
Q7. Statement-I :Molecules that are not superimposable on their mirror images are chiral Because
Statement-II :All chiral molecules have chiral centres. [IIT JEE - 2007]
(A) Statement-1 is True, Statement-2 is True ; Statement-2 is a correct explanation for
Statement-1
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1
(C) Statement-1 is True, Statement-2 is False.
(D) Statement- 1 is False, Statement- 2 is True.
APNI KAKSHA 35
Q8. The correct statement(s) concerning the structures E, F and G is (are) [IIT JEE - 2008]
(A) E, F and G are resonance structures (B) E, F and E, G are tautomers

(C) F and G are geometrical isomers (D) F and G are diastereomers
Q9. The correct statement(s) about the compound given below is (are) [IIT JEE - 2008]
(A) The compound is optically active

(B) The compound possesses centre of symmetry
(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry
Q10. The correct statement(s) about the compound
H3 C(HO)HC − CH = CH − CH(OH)CH3 (X) is (are): [IIT JEE - 2009]
(A) The total number of stereoisomers possible for X is 6
(B) The total number of diastereomers possible for X is 3
(C) If the stereochemistry about the double bond in X is trans, the number of enantiomers
possible for X is 4
(D) If the stereochemistry about the double bond in X is cis, the number of enantiomers
possible for X is 2
Q11. In the Newman projection for 2,2–dimethylbutane [IIT JEE - 2010]
X and Y can respectively be

(A) H and H
(B) H and C2 H5
(C) C2 H5 and H
(D) CH3 and CH3
APNI KAKSHA 36
Q12. Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct ?
[IIT JEE – 2012]
(A) M and N are non-mirror image stereoisomers

(B) M and O are identical
(C) M and P are enantiomers
(D) M and Q are identical
Q13. The total number(s) of Stable conformers with non-zero dipole moment for the following
compound is (are) [IIT JEE - 2014]
Q14. The total number of stereoisomers that can exist for M is : [IIT JEE - 2015]
Q15. In the following monobromination reaction, the number of possible chiral products is
[IIT JEE - 2016]
Q16. For the given compound X, the total number of optically active stereoisomers is
[IIT JEE - 2018]
APNI KAKSHA 37
Q.17 Newman projections 𝐏, 𝐐, 𝐑 and 𝐒 are shown below: [IIT JEE - 2020]
Which one of the following options represents identical molecules?
(A) P and Q
(B) Q and S
(C) Q and R
(D) R and S
Q.18 The Fischer projection of D-erythrose is shown below. [IIT JEE - 2020]
D-Erythrose and its isomers are listed as P, Q, R, and S in Column-I. Choose the correct
relationship of P, Q, R, and S with D-erythrose from Column II.
APNI KAKSHA 38
(A)P → 2, Q → 3, R → 2, S → 2
(B) P → 3, Q → 1, R → 1, S → 2
(C) P → 2, Q → 1, R → 1, S → 3
(D) 𝑃 → 2, 𝑄 → 3, 𝑅 → 3, 𝑆 → 1
Q.19 Question 6: An organic compound (C8 H10 O2 ) rotates plane-polarized light. It produces pink
color with neutral FeCl3 solution. What is the total number of all the possible isomers for this
compound? [IIT JEE - 2020]
APNI KAKSHA 39
ANSWER KEY
EXERCISE I (MAINS ORIENTED)
Q1. (D) Q2. (D) Q3. (A) Q4. (A) Q5. (A) Q6. (B) Q7. (B)
Q8. (D) Q9. (C) Q10. (C) Q11. (C) Q12. (D) Q13. (C) Q14. (A)
Q15. (C) Q16. (A) Q17. (C) Q18. (D) Q19. (B) Q20. (C) Q21. (B)
Q22. (B) Q23. (ACD) Q24. (B) Q25. (C) Q26. (A) Q27. (B) Q28. (B)
Q29. (A) Q30. (C) Q31. (A) Q32. (D) Q33. (B) Q34. (A) Q35. (B)
EXERCISE-II (JEE ADVANCE ORIENTED LEVEL-II)
1. B 2. B 3. A 4. ACD 5. AC 6. BCD
7. BCD 8. BC 9. C 10. ABD 11. CD 12. AD
13. C 14. ABCD
15. (A) → P ; (B) → R ; (C) → Q ; (D) → R
16. (A) → P,Q ; (B) → Q,S ; (C) → Q,R,S ; (D) → Q,R,S
17. (A) → Q; (B) → T; (C) → S; (D) → P,S; (E) → P,R;
18. 11 19. (i) 6, (ii) 8 20. 6 21. 8 22. 6
23. Achiral : I, III , IV ; chiral : II,V, VI, VII
24. 8 25. 4 26. 8 27. 3 28. 424 29. 8
30. 3
EXERCISE-III (JEE ADVANCE ORIENTED LEVEL-II)
Q1. (i)(B); (ii)(C) Q2. (C) Q3. (C) Q4. (AD) Q5. (ACD)
Q6. (C) Q7. (B) Q8. (CD) Q9. (D) Q10. (C) Q11. (C)
Q12. (A) Q13. (C)
Q14. (A) → P ; (B) → Q ; (C) → R,S ; (D) → S
Q15. (A) → 4-iii ; (B) → 3-iv ; (C) → 2-ii ; (D) → 1-i
Q16. Optical : a,b,c,d,f,g,i,j,k ; Geometrical isomer : c,g,j ; None : e, h
Q17. (10)
Q18. (a) Enantiomers, (b) Enantiomers, (c) Geometrical isomers & Diastereomers,
(d) Positional, (e) Optical, (Diastereomers), (f) Diastereomers
(g) Enantiomers, (h) Identical, (i) Geometrical isomers (Diastereomers)
Q19. (7)
Q20. (3)
Q21. (i) 24 (ii) 9 (iii) 4 (iv) 4 (v) 0, (vi) 4 (vii) 25 , (viii) 24 , (ix) 2, (x) 4, (xi) 3
Q22. (2)
APNI KAKSHA 40
EXERCISE-IV (A) (JEE MAINS)
Q1. (D) Q2. (D) Q3. (B) Q4. (B) Q5. (C) Q6. (A)
Q7. (C) Q8. (C) Q9. (B) Q10. (A) Q11. (D) Q12. (C)
Q13. (C) Q14. (D) Q15. (D) Q16. (A) Q17. (2) Q18. (8)
EXERCISE-IV (B) (JEE ADVANCED)
Q1. (B) Q2. (B) Q3. (A)
Q4. Enantiomers - I and III ; Diastereomers - I & II and II & III
Q5. (D) Q6. (B) 7. (C) 8. (BCD) 9. (AD) 10. (AD)
11. (BD) 2. (ABC) 13. (3) 14. (2) 15. (5) 16. (7)
Q17. (C) Q18. (C) Q19. (C)
APNI KAKSHA 41
(Organic Chemistry) CARBOCATION AND FREE RADICAL
EXERCISE – I (MAINS ORIENTED)
1. Which of the following carbocation is most stable?
(A) (B)
(C) (D)
2. Which carbocation is least likely to be formed as an intermediate ?
+ +
(A) (C6 H5 )3 C (B) (C) (D) CH3 − CH2
3. Which one of the following carbocation would you expect to rearrange :
(A) (B) (C) (D)
4. How many 1, 2-shifts are involved during the course of following reaction :
(A) 1 (B) 2 (C) 3 (D) 4
5. How many following carbocation undergo re-arrangement?

(a) CH3 CH2 CH2+ (b) (CH3 )2 CHCH + HCH3 (c) (CH3 )3 CCHCH3
(d) (CH3 CH2 )3 CCH2+ (e) (f)
(g) (h)
(A) 5 (B) 8 (C) 6 (D) 7
APNI KAKSHA 1
6. For the reactions
(I)
(II)
(III)
(IV)
The correct decreasing order of enthalpies of reaction for producing carbocation is

(A) ΔH10 > ΔH20 > ΔH30 > ΔH40 (B)ΔH40 > ΔH10 > ΔH20 > ΔH30
(C) ΔH30 > ΔH20 > ΔH10 > ΔH40 (D) ΔH20 > ΔH10 > ΔH40 > ΔH30
7. Which is not the correct statement for given compound :
(A) I is more soluble than bromocyclopropane

(B) I gives pale yellow ppt. on addition with AgNO3
(C) I has lower dipole moment than bromocyclopropane
(D) On reaction with AlBr3 , I will produce aromatic compound having 3 equivalent resonating
structures
8. A solution of (−) − 1-chloro-1-phenylethane in toluene racemises slowly in the presence of a

small amount of SbCl5 , due to the formation of :
(A) carbanion (B) carbene (C) carbocation (D) free radical
9. How many 1, 2-Shifts are involved during the course of following reaction :
(A) 1 (B) 0 (C) 3 (D) 4
APNI KAKSHA 2
10. Major product of following reaction is :
(A) (B)
(C) (D)
(A) (B) (C) (D)
12. Among the given compounds, the correct dehydration order is :
(A) I < II < III < IV (B) II < III < IV < I
(C) I < III < IV < II (D) I < II < III = IV
(A) (B)
(C) (D)
APNI KAKSHA 3
14. Rate of dehydration when given compounds are treated with conc. H2 SO4 :
(A) (B)
(C) (D)
15. One of the major product of following reaction is :
(A) (B) (C) (D)
(A) (B)
(C) (D)
APNI KAKSHA 4
(A) (B)
(C) (D)
18. What is the decreasing order of rate of reaction with HBr for the following benzyl alcohol and its
derivative:
(A) A > C > D > B (B) A > B > D > C

(C) D > C > B > A (D) A > B > C > D
19. Which will dehydrate at fastest rate by H3 PO4 :

(A) 2-methyl butan-2-ol (B) 3-methyl butan-2-ol
(C) Butan-1-ol (D) 2-methyl butan-1-ol
20. The double bond which is most reactive towards electrophile :
(A) a (B) b (C) c (D) None
APNI KAKSHA 5
21. The major product formed in the following reaction is :
(A) (B)
(C) (D)
22. How many products are obtained in the given reaction :
(A) 1 (B) 2 (C) 3 (D) 4
23. Compare rate of reaction towards pinacol to pinacolone rearrangement.
(A) II > III > I (B) III > II > I

(C) II > I > III (D) I > II > III
APNI KAKSHA 6
(A) (B)
(C) (D)
25. What is the order of reactivity with HBr :
(A) a > b > c (B) b > a > c (C) c > b > a (D) b > c > a
26. In the given reaction, (X) can not be :
(A) (B)
(C) (D)
27. Major product of the reaction is :
(A) (B)
(C) (D)
APNI KAKSHA 7
(A) (B)
(C) (D)
29. Arrange the following compounds in decreasing order of electrophilic addition :
(A) P > Q > R (B) P > R > Q

(C) R > P > Q (D) R > Q > P
30. Major product mixture (without rearrangement of carbocation) of following reaction is :
(A) Racemic mixture (B) Optically inactive

(C) Mixture of diastereomers (D) Meso product
31. Correct statement regarding products P, Q & R is :
(A) Product P & R are same (B) Product Q & R are same
(C) P & Q are functional isomers (D) Product P, Q & R all are different
APNI KAKSHA 8
32. Select the incorrect statement about the product mixture in the following reaction :
(A) It is optically active (B) It is racemic mixture

(C) It is a resolvable mixture (D) It is a mixture of erythro compounds
33. Which of the following is not correct about P2 :
(A) It is a spiro compound (B) It is a Ketone

(C) It can show tautomerism (D) Its double bond equivalent is 4
(A) (B)
(C) (D)
35. Select incorrect statements about the product (P) of the reaction :
(A) P is optically inactive due to internal compensation

(B) P is optically inactive due to the presence of plane of symmetry in the molecule
(C) The structure of P can have three optical isomers possible.
(D) P can have four possible optical isomers.
APNI KAKSHA 9
36. Which of the following will produce vicinal dibromide on reaction with Conc. HBr ?
(A) Alkyne (B) Allene (C) Vinyl bromide (D) Allyl bromide
37. Consider the following groups, the order of leaving group nature is: :
(I) −OAc (II) −OMe (III) −OSO2 Me (IV) −OSO2 CF3
(A) I > II > III > IV (B) IV > III > I > II
(C) III > II > I > IV (D) II > III > IV > I
38. The correct order of rate of following Wurtz recations :
(I)
(II)
(III)
(IV)
(A) I > II > III > IV (B) II > I > III > IV
(C) IV > III > II > I (D) In all rate of Wurtz reaction is same
(A) (B)
APNI KAKSHA 10
40. Find out the correct order of rate of reaction towards free radical allylic substitution :
(A) I > II > III (B) II > I > III

(C) III > II > I (D) III > I > II
APNI KAKSHA 11
EXERCISE – II-(A)
1. Among the isomeric alkanes of molecular formula " C5 H12", which of the following yields four
structures of monochlorides on photochemical chlorination.
(A) (B) (C) (D)
2. Products which can be obtained during the reaction in good yield:
(A) (B)
(C) (D)
3. Correct statement(s) for the monochlorinated products of following reaction.
(A) Four different products are formed

(B) Two optically active products are formed
(C) The optically active compound formed here can also be made by the reaction of HCl
(D) The reaction path is free radical substitution.
4. In the given reaction, find out the correct statement(s)
(A) It gives total 9 allylic brominated products

(B) 6 fractions are obtained on fractional distillation of product mixture
(C) Substrate has 7 allylic hydrogens
(D) NBS is a brominating agent for allylic positions
APNI KAKSHA 12
5. Which of the following can be produced by Wurtz reaction in good yield:
(A) (B) (C) (D)
6. Products formed when HCl adds to 2,4 -hexadiene is :

(A) 4-chloro-2-hexene
(B) 2-chloro-3-hexene
(C) 2-chloro-4-hexene
(D) 1-chloro-2-hexene
7. Correct statements among the following is/are :

(A) Dihaloalkanes having the same type of halogen atoms on same atom are named as
alkylidene dihalides
(B) Dihaloalkanes having the same type of halogen atoms on adjacent atoms are named as
alkylene dihalides
(C) In common name system gem-dihalides are named as alkylidene halide
(D) In common name system vic-dihalides are named as alkylene halide
8. Which of the following is(are) correct order of nucleophilicity?
(A) (B) HOO− > HO− in DMSO
(C) H2 S > H2 O (D)
9. Which of following reaction products are diastereomer of each other:
(A) (B)
(C) (D)
APNI KAKSHA 13
10. Which of following reaction products are diastereomer of each other:
(A) (B)
(C) (D)
11. Correct statements for given reaction is (are):
(A) Product mixture is resolvable

(B) Product can be separated by fractional distillation of mixture
(C) Two products possible & both are optically active
(D) Products are diastereomer
12. Which of the following can be formed during this reaction?
(A) (B)
(C) (D)
APNI KAKSHA 14
(A) (B) (C) (D)
14. Major product (Q) of following reaction is :
(A) (B)
(C) (D)
15. Select True statement(s) :

(A) Cyclopropane decolorizes bromine water
(B) In general, bromination is more selective than chlorination.
(C) The 2,4,6-tri-tert, butylphenoxy radical is resistant to dimerization.
(D) The radical-catalysed chlorination, ArCH3 → ArCH2 Cl, occurs faster when Ar = phenyl than
when Ar = p-nitrophenyl.
APNI KAKSHA 15
16. Number of following reactions which produces hydrocarbon as major product ?
(A) 2 (B) 4 (C) 5 (D) 6

17. Correct statement regarding major product is/are :
(A) odd no. of double bond equivalent in product

(B) product is bicyclic compound
(C) product can show geometrical isomerism
(D) reaction involve carbocation as intermediate
(A) (B)
(C) (D)
APNI KAKSHA 16
EXERCISE # II-B
1. Statement-1: HBr shows antimarkownikoff's addition on propene but not HCl.
Statement-2: H − Br is stronger acid than H − Cl.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for
statement 1 .
(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for
statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.
2. Each of the compounds in column A is subjected to further chlorination. Match the following
for them:
Column-A Column-B
(A) CHCl2 − CH2 − CH3 (P) Optically active original compound
(B) CH2 Cl − CHCl − CH3 (Q) Only one trichloro product
(C) CH2 Cl − CH2 − CH2 − Cl (R) Three trichloro product.
(D) CH3 − CCl2 − CH3 (S) Four trichloro product
(E) (T) Atleast one of the trichloro product is optically active
(U) Two trichloro products.
3. Column-I (Intermediate) Column-II

(A) Carbocation (P) Kolbey Electrolysis
(B) Carbanion (Q) Wurtz reaction
(C) Free radical (R) Dehydration of alcohol
(D) Octet complete in one of the intermediate sodalime (S) Monocarboxylic acid with
APNI KAKSHA 17
4. Match the Column.
Column-I (Reaction) Column-II (Potential Energy Curve)
(A) (P)
(B) (Q)
(C) (R)
(D) (S)
5. RCl is treated with Li in ether to form R − Li, R − Li reacts with water to form isopentane.
R − Cl also reacts with sodium to form 2, 7-dimethyloctane. What is the structure of R − Cl.
6. A chloroderivative ' X ' on reduction gave a hydrocarbon with five carbon atoms in the
molecule. When X is dissolved in ether and treated with sodium, 2, 2, 5, 5-tetramethyl hexane is
obtained. What is compound X.
APNI KAKSHA 18
7. With the help of following data show HBr exhibits the peroxide effect.
ΔH10 /kJmol−1 ΔH20 /kJmol−1
H−X Ẋ + CH2 = CH2 → XCH2 − ĊH2 XCH2 − ĊH2 + H − X → XCH2 CH3 + Ẋ

HCl –67 +12.6
HBr –25.1 –50.2
HI +46 –117.1
8. Write all the monochlorinated products (including stereo) of isohexane.
9. What are the products of the following reactions?
(A) PhCH = CHCH3 + HBr ⟶ A (B)
(C) (D)
10. It required 0.7 g of a hydrocarbon (A) to react completely with Br2 (2.0 g) and form a non
resolvable product. On treatment of (A) with HBr it yielded monobromo alkane (B). The same
compound (B) was obtained when (A) was treated with HBr in presence of peroxide. Write
down the structure formula of (A) and (B) and explain the reactions involved.
11. Complete following reaction :
12. CH ≡ C − CH2 − CH = CH2 , adds up HBr to give CH ≡ C − CH2 − CHBr − CH3 while
CH ≡ C − CH = CH2 adds up HBr to give CH2 = C. Br. CH = CH2 .
APNI KAKSHA 19
13. In study of chlorination of propane four products (A, B, C, D) of molecular formula C3 H6 Cl2
were obtained. On further chlorination of the above products A gave one trichloro product, B
gave two whereas C and D gave three each. When optically active C was chlorinated one of
trichloro propanes was optically active and remaining two were optically inactive. Identify the
structures of A, B, C and D, and explain formation of products.
APNI KAKSHA 20
EXERCISE # JEE-MAINS
1. The reaction of propene with HOCl(Cl2 + H2 O) proceeds through the intermediate :
[JEE MAIN 2016]
(A) CH3 − CHCl − CH2+ (B) CH3 − CH + − CH2 − OH
(C) CH3 − CH + − CH2 − Cl (D) CH3 − CH(OH) − CH2+
2. 3-Methyl-pent-2-ene on reaction with HBr in presence of peroxide forms an addition
product. The number of possible stereoisomers for the product is :- [JEE MAIN 2017]
(A) Six (B) Zero (C) Two (D) Four
3. The increasing order of nucleophilicity of the following nucleophiles is:
[JEE MAIN-2019]
⊖
(a) CH3 COΘ
2 (b) H2 O (c) CH3 SOΘ
3 (d) O H
(A) (b) < (c) < (d) < (a) (B) (b) < (c) < (a) < (d)
(C) (a) < (d) < (c) < (b) (C) (d) < (a) < (c) < (b)
4. The major product of the following addition reaction is: [JEE MAIN-2019]
(A) (B)
(C) (D)
5. An 'Assertion' and a 'Reason' are given below. Choose the correct answer form the following
options: [JEE MAIN-2019]
Assertion (A): Vinyl halides do not undergo nucleophilic substitution easily.
Reason (R): Even though the intermediate carbocation is stabilized by loosely held π electrons,
the cleavage is difficult because of strong bonding.
(A) (A) is a correct statement but (R) is a wrong statement.
(B) Both (A) and (R) are correct statements but (R) is not the correct explanations of (A).
(C) Both (A) and (R) are wrong statements
(D) Both (A) and (r) are correct statements and (R) is the correct explanation of (A).
6. Which one of the following alkenes when treated with HCl yields majorly an anti Markovnikov
product? [JEE MAIN-2019]
(A) F3 C − CH = CH2 (B) H2 N − CH = CH2
(C) CH3 O − CH = CH2 (D) Cl − CH = CH2
APNI KAKSHA 21
7. The major product of the following reaction is: [JEE MAIN-2019]
CH3C  CH ⎯⎯⎯⎯⎯
(i)DCl(1equic)
(ii)DI
→
(A) CH3 CD(I)CHD(Cl) (B) CH3 CD(Cl)CHD(I)

(C) CH3 CD2 CH(Cl)(I) (D) CH3 C(I)(Cl)CHD2
8. The major products A and B in the following reactions are : [JEE MAIN-2020]
(A)
(B)
(C)
(D)
9. The major product of the following reaction is : [JEE MAIN-2020]
(A) (B)
(C) (D)
APNI KAKSHA 22
10. The major product in the following reaction is : [JEE MAIN-2020]
(A) (B)
(C) (D)
11. The major product [B] in the following sequence of reactions is : [JEE MAIN-2020]
(A) (B)
(C) (D)
12. Given below are two statements : one is labelled as Assertion (A) and the other is labelled as
Reason (R).
Assertion (A) : Treatment of bromine water with propene yields 1-bromopropan-2-ol.
Reason (R) : Attack of water on bromonium ion follows Markovnikov rule and results in 1-
bromopropan −2 − ol.
In the light of the above statements, choose the most appropriate answer from the options
given below : [JEE MAIN-2021]
(A) Both (A) and (R) are true but (R) is NOT the correct explanation of (A).
(B) (A) is false but (R) is true.
(C) Both (A) and (R) are true and (R) is the correct explanation of (A)
(D) (A) is true but (R) is false.
APNI KAKSHA 23
C2 H3 OH ′A′
13. In the given reaction 3 -Bromo-2, 2 -dimethyl butane ⟶ Product A is:
(Major Product)
[JEE MAIN-2021]
(A) 2-Ethoxy-3, 3-dimethyl butane
(B) 1-Ethoxy-3, 3-dimethyl butane
(C) 2 -Ethoxy-2, 3 -dimethyl butane
(D) 2-Hydroxy-3, 3-dimethyl butane
14.
Consider the above reaction, the major product ' P ′ is: [JEE MAIN-2021]
(A) (B)
(C) (D)
15.
Consider the above reaction, the major product " P " formed is :- [JEE MAIN-2021]
(A) (B)
(C) (C)
APNI KAKSHA 24
16.
consider the above reaction, and choose the correct statement: [JEE MAIN-2021]
(A) The reaction is not possible in acidic medium
(B) Both compounds A and B are formed equally
(C) Compound A will be the major product
(D) Compound B will be the major product
hv
17. (C7 H5 O2 )2 ⟶ [X] + 2Ċ6 H5 + 2CO2
Consider the above reaction and identify the intermediate ' X ' [JEE MAIN-2022]
(A) (B) (C) (D)

18. The major product (P) of the given reaction is (where, Me is −CH3 ) [JEE MAIN-2022]
(A) (B) (C) (D)

19. The major product 'A' of the following given reaction has _____ sp2 hybridized carbon atoms.
2,7 - Dimethyl1 - 2,6-octadiene
H+ A
⟶ [JEE MAIN-2022]
Major product
20. The products formed in the following reaction. [JEE MAIN-2022]
(A) (B)
(C) (D)
APNI KAKSHA 25
21. Arrange the following in increasing order of reactivity towards nitration [JEE MAIN-2022]
A. p-xylene B. bromobenzene C. mesitylene D. nitrobenzene E. benzene
Choose the correct answer from the options given below
(A) C < D < E < A < B (B) D < B < E < A < C
(C) D < C < E < A < B (D) C < D < E < B < A
22. Choose the correct option for the following reactions. [JEE MAIN-2022]
(A) 'A' and 'B' are both Markovnikov addition products.

(B) ' A ' is Markovnikov product and ' B ' is antiMarkovnikov product.
(C) ' A ' and ' B ' are both anti-Markovnikov products.
(D) ' B ' is Markovnikov and ' A ' is antiMarkovnikov product.
23. In the following given reaction ' A ' is [JEE MAIN-2023]
(A) (B) (C) (D)
24. The compound which will have the lowest rate towards nucleophilic aromatic substitution on
treatment with OH − is [JEE MAIN-2023]
(A) (B) (C) (D)
25. Find out the major product for the following reaction. [JEE MAIN-2023]
(A) (B) (C) (D)
APNI KAKSHA 26
26. The major products ' A ' and ' B ', respectively, are [JEE MAIN-2023]
(A)
(B)
(C)
(D)
27. [JEE MAIN-2023]
(A) (B) (C) (D)
APNI KAKSHA 27
EXERCISE – JEE -ADVANCE (OBJECTIVE)
1. Benzyl chloride (C6 H5 CH2 Cl) can be prepared from toluene by chlorination with: [IIT 1998]
(A) SO2 Cl2 (B) SOCl2 (C) Cl2 , (hv) (D) NaOCl
2. Which of the following has the highest nucleophilicity? [IIT 2000]
(A) F − (B) OH − (C) CH3− (D) NH2−
3. In the following reaction, the major product is [IIT 2015]
(A) (B)
(C) (D)
4. The correct statement(s) for the following addition reactions is (are) [IIT 2017]
(A) (M and O) and ( N and P) are two pairs of diastereomers

(B) Bromination proceeds through trans-addition in both the reactions
(C) O and P are identical molecules
(D) (M and O) and ( N and P) are two pairs of enantiomers
5. Choose the correction option for the following reaction [IIT 2019]
APNI KAKSHA 28
(A) (B)
(C) (D)
6. Consider the following transformations of a compound P. [IIT 2020]
Choose the correct option(s).
APNI KAKSHA 29
7. Match the reactions in List-I with the features of their products in List-II and choose the correct
option. [IIT 2023]
List-I List-II
(P) (1) Inversion of configuration
(Q) (2) Retention of configuration
(R) (3) Mixture of enantiomers
(S) (4) Mixture of structural

isomers
(5) Mixture of diastereomers
(A) P → 1; Q → 2; R → 5; S → 3
(B) P → 2; Q → 1; R → 3; S → 5
(C) P → 1; Q → 2; R → 5; S → 4
(D) P → 2; Q → 4; R → 3; S → 5
APNI KAKSHA 30
ANSWER KEY
EXERCISE - I (MAINS ORIENTED)
1. (C) 2. (C) 3. (B) 4. (D) 5. (B) 6. (B) 7. (C)
8. (C) 9. (B) 10. (A) 11. (D) 12. (A) 13. (D) 14. (C)
15. (D) 16. (D) 17. (A) 18. (D) 19. (A) 20. (B) 21. (C)
22. (B) 23. (C) 24. (D) 25. (B) 26. (D) 27. (D) 28. (B)
29. (B) 30. (C) 31. (A) 32. (A) 33. (D) 34. (D) 35. (D)
36. (D) 37. (B) 38. (C) 39. (C) 40. (C) 41. (B) 42. (C)
43. (B) 44. (A) 45. (A) 46. (C) 47. (A) 48. (BD 49. (C)
50. (B) 51. (B) 52. (A) 53. (B)
EXERCISE II-(A)
1. C 2. AB 3. ABD 4. ACD 5. BD 6. AB 7. ABCD
8. BCD 9. AD 10. AB 11. AC 12. ABD 13. B 14. C
15. ABCD 16. B 17. ABC 18. AC
EXERCISE II-(B)
1. B 2. (A) → S, T; (B) → P, S, T; (C) → U; (D) → Q; (E) → T, U
3. (A) → R; (B) → Q, S; (C) → P, Q; (D) → Q, S 4. (A) → P; (B) → P; (C) → Q; (D) → R;
5. 1-chloro-3-methylbutane 6.
7.
APNI KAKSHA 31
8.
9. Not available.
10. (a)
(b)
11. Not available.

12. Not available.
13. Not available.
EXERCISE (JEE MAIN)
1. (3) 2. (4) 3. (4) 4. (2) 5. (1) 6. (1) 7. (4)
8. (3) 9. (1) 10. (3) 11. (3) 12. (C) 13. (C) 14. (C)
15. (B) 16. (C) 17. (D) 18. (C) 19. (B) 20. (B) 21. (B)
22. (B) 23. (D) 24. (D) 25. (B) 26. (A) 27. (A)
EXERCISE (JEE ADVANCE - Objective)
1. (A,C) 2. (C) 3. (D) 4. (A,B) 5. (A,D) 6. (B,C) 7. (B)
APNI KAKSHA 32
5. Sol.
6. Sol.
APNI KAKSHA 33
SOLUTION
12.
Its IUPAC name 1-bromopropan-2-ol
A and R are true and (R) is the correct explanation of (A).
13.
APNI KAKSHA 34
14.
15.
APNI KAKSHA 35
16.
17.
18.
APNI KAKSHA 36
19.
20.
21.
−NO2 is strongly deactivating
−Br − deactivating
−CH3 − activating group

D<B<E<A<C
APNI KAKSHA 37
22.
23.
24. Electron withdrawing groups are highly ineffective at meta position in nucleophilic aromatic
substitution reactions.
Hence compound will have lowest
rate in nucleophilic aromatic substitution.
25.
APNI KAKSHA 38
26.
27.
APNI KAKSHA 39
(Organic Chemistry) SUBSTITUTION ELIMINATION
EXERCISE - I (MAINS ORIENTED)
1. Major product of following reaction is:
(A) (B)
(C) (D)
2. Which compound undergoes hydrolysis by the SN 1 mechanism at the fastest rate?
(A) (B)
(C) (D)
3. Arrange the following compounds in decreasing order of their reactivity for hydrolysis reaction
(I) C6 H5 − CH2 − Br (II) (II) (II)
(A) I > II > III > IV (B) IV > II > I > III
(C) III > IV > II > I (D) IV > III > II > I
4. Arrange the following compounds in order of decreasing rate of hydrolysis for SN 1 reaction:
(A) (B) (C) (D)
APNI KAKSHA 1
5. Which of the following is most reactive toward SN 1 reaction?
(I) (II)
(III) (IV)
(A) II > III > IV > I (B) IV > III > II > I
(C) III > IV > II > I (D) I > II > III > I
6. Arrange the following compounds in order of decreasing rate of hydrolysis for SN 1 reaction:
(A) (B)
(C) (D)
7. Consider the SN 1 solvolysis of the following halides in aqueous formic acid, decide decreasing
order of reactivity of above alkyl halide?
(I) (II)
APNI KAKSHA 2
(III) (IV)
(A) III > IV > II > I (B) II > IV > I > III
(C) I > II > III > IV (D) III > I > II > IV
8. For the given reaction, which substrate will give maximum racemisation?
(A) (B)
(C) (D)
APNI KAKSHA 3
(C) (B) (C) (D) None of these
10. If 96% racemisation takes place in given reaction then find out the correct statement:
(A) Among the products 48% S and 48%R configuration containing molecules are present
(B) Among the products 50% S and 50%R configuration containing molecules are present
(C) Among the products 48% S and 52%R configuration containing molecules are present
(D) Among the products 52% S and 48%R configuration containing molecules are present
11. In the given reaction the product [P] can be :
(A) CH3 − CH = CH − CH2 − Br (B)
(C) CH2 = CH − CH = CH2 (D)
12. Which of the following can not give SN 1 reaction easily?
(A) (B) (C) (D)

13. Which one of the following compounds will be most reactive for SN 1 reactions?
APNI KAKSHA 4
14. Which of the following compounds is most rapidly hydrolysed by SN 1 mechanism?
(A) C6 H5 Cl (B) Cl − CH2 − CH = CH2
(C) (C6 H5 )3 CCl (D) C6 H5 CH2 Cl
15. Among the bromides I − III given below, the order of reactivity in SN 1 reaction is:
(A) III > I > II (B) III > II > I

(C) II > III > I (D) II > I > III
16. Which of the following is most reactive toward SN 2.
(A) (B) (C) (D)
17. Which of the following is most reactive toward SN 2.

CH3 Br + OH − ⟶ CH3 OH + Br −
(A) Rate = k[CH3 Br] (B) Rate = k[OH − ]
(C) Rate = k[CH3 Br][OH − ] (D) Rate = k[CH3 Br]o [OH − ]o
18. Select suitable reason for non-occurence of the following reaction.

Br − + CH3 OH ⟶ BrCH3 + OH −
(A) Attacking nucleophile is stronger one
(B) Leaving group is a stronger base than nucleophile
(C) Alcohols are not good substrate for SN reaction
(D) Hydroxide ions are weak bases
APNI KAKSHA 5
(A) (B)
(C) Both (D) None of these
20. The reactivity of given compounds towards SN 2 displacement is :

2-bromo-2-methylbutane 1-bromopentane 2-bromopentane
(I) (II) (III)
(A) I > II > III (B) I > III > II
(C) II > III > I (D) II > I > III
21. For the given reaction, CORRECT option regarding mechanism involved is :
(A) I can't be SN 1 (B) II can't be SN 2

(C) I can be SN 1& II can be SN 2 (D) I can be SN 2& &I can be SN 1
22. In which of the following replacement of Cl− is most difficult?
(A) (B) (C) (D)
23. Arrange these compounds in order of increasing SN 2 reaction rate :
(A) III < I < II < IV (B) III < II < I < IV
(C) IV < III < I < II (D) III < IV < I < II
24. Which reaction proceeds faster with NaI in DMSO?
APNI KAKSHA 6
(A) (B)
(C) (D)
25. The major product in the given reaction is:
(A) (B)
(C) (D) All of these
26. The compound CH3 − O − CH2 − Br gives faster rate of nucleophilic substitution reaction than :
(A) CH3 Br (B) CH3 CH2 Br
(C) PhCH2 Br (D) CH3 OCH2 Cl
27. Which will give white ppt. with AgNO3 ?
(A) (B)
(C) (D) Both (A) and (C)

28. When ethyl bromide is treated with moist Ag 2 O, the main product is:
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All of these
APNI KAKSHA 7
29. When ethyl bromide is treated with dry Ag 2 O, the main product is:
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All of these
(A) (B) (C) H2 C = CH2 (D)
31. Which reaction conditions (reagents) is suitable for the following reaction:
Br
(A) CCl2 (B) SOBr2 (C) PBr3 (D) HBr/ conc H2 SO4
4
(A) (B)
(C) (D)
33. Assuming all the substrate convert into substitution products containing 0.05 mole of
Configuration, calculate the percentage of SN 2 mechanism.
APNI KAKSHA 8
(A) 90% (B) 80% (C) 70% (D) 95%
34. The reaction of SOCl2 on alkanols to form alkyl chlorides gives good yields because
(A) Alkyl chlorides are immiscible with SOCl2
(B) The other products of the reaction are gaseous and escape out
(C) Alcohol and SOCl2 are soluble in water
(D) The reaction does not occur via intermediate formation of an alkyl chloro sulphite
(A) (B) (C) H2 C = CH2 (D)
35. In the given pairs, which pair represent correct order of rate dehydrohalogenation reaction.
(A) (B)
(C) (D) CH3 − CH2 − Cl < CD3 − CD2 − Cl
APNI KAKSHA 9
(A) (B)
(C) (D)
(A) (B)
(C) (D)
39. CORRECT order of rate of reaction for following compounds with Conc. HBr is:
CH3 OH CH3 CH2 OH (CH3 )2 CHOH (CH3 )3COH
(P) (Q) (R) (S)
(A) S > R > Q > P (B) P > Q > R > S
(C) S > R > P > Q (D) P > S > Q > R
40. If P&Q are the major products then P&Q are respectively:
APNI KAKSHA 10
(A) (B)
(C) (D)
41. On heating glycerol with excess amount to HI, the product formed is
(A) Allyl iodide (B) Isopropyl iodide
(C) Propylene (D) 1,2,3-tri-iodopropane
(A)
(B)
(C) (D)
APNI KAKSHA 11
EXERCISE # II-A
1. Rate of SN 2 depends on:
(A) Conc of Nucleophile (B) Conc of substrate
(C) Nature of leaving group (D) Nature of solvent
2. In the given pair in which pair the first compound is more reactive than second towards SN 2
reaction.
(A)
(B)
(C)
(D)
3. Which of following statements is(are) correct for the given reaction.
(A) Product formation takes place due to the breaking of C − O bond

(B) Hydrolysis of major product gives optically active carboxylic acid
(C) Reaction involves bimolecular nucleophilic substitution reaction
(D) Absolute configuration of major product is " R "
APNI KAKSHA 12
4. Which of the following statements is / are true?
(A) CH3 − CH2 − CH2 − I will react more readily than (CH3 )2 CHI for SN 2 reactions.
(B) CH3 − CH2 − CH2 − Cl will react more readily than CH3 − CH2 − CH2 − Br for SN 2 reaction.
(C) CH3 − CH2 − CH2 − CH2 − Br will react more readily than (CH3 )3 C − CH2 − Br for SN 2
reactions
(D) CH3 − O − C6 H4 − CH2 Br will react more readily than NO2 − C6 H5 − CH2 Br for SN 2
reaction
5. Incorrect statement about alkyl halides is / are:

(A) Tertiary alkyl halides undergo SN 2 substitutions
(B) Alkyl iodides on exposure to sunlight gradually darken
(C) Photo iodination is irreversible in presence of HIO3
(D) A nucleophilic substitution is most difficult in alkyl iodides
6. Which of following reaction(s) produce Saytzeff product as a major product:
(A) (B)
(C) (D)
7. SN 1& SN 2 is not favourable in

(A) H2 C = CH − Cl (B) Ph − CH2 − Cl
(C) Ph − Cl (D) H2 C = CH − CH2 − Cl
8. Among the following, which statement is correct?

(A) Alkyl-aryl product can be obtained in wurtz reaction.
(B) Dipole moment of cyclohexyl chloride is more than that of chlorobenzene.
(C) Alchohols are insoluble in lucas reagent while their halides are soluble.
(D) Preparation of ether by acid dehydration of secondary alcohol is not suitable.
APNI KAKSHA 13
9. In which of the following reaction(s), configuration about chiral carbon is retained in the major
product
(A) (B)
(C) (D)
10. A gem dichloride is formed in the reaction:

(A) CH3 CHO and PCl5 (B) CH3 COCH3 and PCl5
(C) CH2 = CH2 and Cl2 (D) CH2 = CHCl and HCl
11. Assuming that all products are major & R is hydrocarbon while T is also organic product then
choose the correct option(s)?
(A) T is more acidic than P

(B) R has more heat of combustion than propene
(C) Both P & Q can show stereoisomerism
(D) S is not an organic product
12. Which of following are correct for given reaction
(A) Major product of reaction is

(B) Major product is
(C) Major product formation involve substitution
(D) The reaction is E2 reaction
APNI KAKSHA 14
13. Which of the following reactions is (are) incorrectly matched with their major product:
HI
(A) Me3 C − O − CH3 ⟶ Me3 C − OH + CH3 I
HI
(B) H3 C − O − CH2 − CH3 ⟶ CH3 OH + ICH2 CH3
(C)
H3 O + 18
(D) CH3 − O − CH2 CH3 ⟶ CH3 OH + CH3 CH2 O H
14. Correct statement among the following is/are:

(A) The rate of hydrolysis of tertiary butyl bromide increases by addition of Ag 2 O
(B) Aqueous Ag 2 O produces nucleophilic OH −
(C) The addition of a small amount of oxygen slows down the photochemical chlorination of
methane.
(D) CH3 CH2 Cl is more reactive than PhCH2 Cl for bimolecular nucleophilic substitution reaction
15. Incorrect statement among the following is/are:

(A) ROH with NaI in the presence of phosphoric acid gives RI, but not in the presence of H2 SO4
(B) 2-methyl propane on chlorination (Cl2 , hv) gives 1-chloro-2-methyl propane while
bromination (Br2 , hv) gives 2-bromo-2-methyl propane
(C) Usually higher temperature prefers substitution over elimination
(D) Triphenyl chloromethane cannot be hydrolysed
16. From left to right, correct statements are:
(A) Rate of SN 1 mechanism increases in polar protic solvent

(B) Rate of SN 2 mechanism increases in DMSO
(C) Rate of E2 mechanism increases
(D) Rate of E1 mechanism increases
APNI KAKSHA 15
17. How many monobromo derivatives are possible for Hydrocarbon (R)?
(A) 2 (B) 3 (C) 5 (D) 1
APNI KAKSHA 16
EXERCISE # II-B
COMPREHENSION TYPE
Groups like CN&[−O − N̈ = O] : possess two nucleophilic centre and are called ambident
nucleophiles. Actually cyanide group is hybride of two contributing structures and therefore
⊖
can act as nucleophile in two different ways [C ≡ N ⟷: C = N ⊖ ] . Similarly nitrite ion also
represents an ambident nucleophile with two different points of linkage [O−= O].
1. Correct option among the following:
(A) (B)
(C) (D)
2. Incorrect statement
(A) KCN is predominentely ionic in nature

(B) AgCN is mainly covalent in nature
(C) In AgCN, carbon is the donor atom
(D) In AgCN nitrogen is the donor atom
3. Match the List I with List II

List-I List-II
(A) (P) Elimination Reaction
(B) (Q) Carbocation
(C) (R) Carbanion
(D) (S) Free radical
APNI KAKSHA 17
List-I List-II
(Reactions) (Products)
⊖
(A) CH3 − O − SO2 CH3 + C2 H5 O (P) CH3 − CH2 − PH2
(B) CH3 − CH2 − I + PH3 (Q) CH3 − O − C2 H5
⊖⊕
(C) HC ≡ C Na + CH3 − CH2 − Br (R) CH3 − O − CH3
Θ
(D) CH3 − Cl + CH3 − O (S) CH ≡ C − CH2 − CH3

⊖
Z − CH2 Br + CH3 O ⟶ Z − CH2 − OCH3 + Br Θ
List-I (Z-) List-II (Relative reactivity)
(A) H − (P) 0.1
(B) CH3 − (Q) 3
(C) C2 H5 − (R) 1
(D) (S) 100

List-I List-II
(A) E1CB (P)
(B) Saytzeff alkene as major product (Q)
(C) E2 (R)
(D) Ei (S)
APNI KAKSHA 18
7. Column-I Column-II
(Reactions) (Characteristics)
HBr
(A) CH3 CH2 CH = CH2 ⟶ (P) Bimolecular
HBr, Peroxide
(B) CH3 CH2 CH = CH2 ⟶ (Q) Carbocation intermediate
SOCl2
(C) PhCH(CH3 )OH ⟶ (R) Regioselective
HBr
(D) PhCH(CH3 )OH ⟶ (S) Racemic modification
(T) Stereospecific reaction
8. Column-I Column-II
(Statements) (Consistent path of reaction)
(A) Reactions are concerted (P) SN 1
(B) CH3 X cannot react (Q) SN 2
(C) 3∘ R − X > 2∘ R − X > 1∘ R − X (R) E1
(D) R − I reacts faster than R − Cl (S) E2
9.
Identify A, C&E in the sequence of reaction.
10. CH3 − CH2 I reacts more rapidly with strong base in comparison to CD3 CH2 I.
11. Predict the product(s) and write the mechanism of the given reaction:
APNI KAKSHA 19
12. What are the products of the following reactions?
(A) (B)
13. A primary alkyl bromide (A), C4 H9 Br, reacted with alcoholic KOH to give compound (B).
Compound (B) reacted with HBr to give an isomer of (A). When (A) was reacted with sodium
metal it gave compound (D), C8 H18 , which was different from the compound produced when n
butyl bromide was reacted with sodium. Draw the structure of (A) and write equations for all
the reactions.
APNI KAKSHA 20
EXERCISE # III (JEE MAIN)
1. Following reaction is an example of : [AIEEE 2002]
(CH3 )3 C − Br + H2 O ⟶ (CH3 )3 C − OH + HBr
(A) Elimination reaction

(B) Free radical substitution
(C) Nucleophilic substitution
(D) Electrophilic substitution
2. SN 1 reaction is feasible in [AIEEE 2002]
(A)
(B)
(C)
(D)
3. Bottles containing C6 H5 I and C6 H5 − CH2 I lost their original labels. They were labelled A and B
for testing. A and B were separately taken in a test tube and boiled with NaOH solution. The
end solution in each tube was made acidic with dilute HNO3 and then some AgNO3 solution
was added. Substance B gave a yellow precipitate. Which one of the following statements is
true for this experiment. [AIEEE 2003]
(A) A was C6 H5 I (B) A was C6 H5 CH2 I
(C) B was C6 H5 I (D) Addition of HNO3 was unnecessary
4. The compound formed on heating chlorobenzene with chloral in the presence of concentrated
sulphuric acid is [AIEEE 2003]
(A) Gammaxe (B) DDT
(C) Freon (D) Hexa chloro ethane
APNI KAKSHA 21
5. The structure of the major product formed in the following reaction is: [AIEEE 2003]
(A) (B)
(C) (D)
6. Which of the following on heating with aqueous KOH, produces acetaldehyde? [AIEEE 2003]
(A) CH2 ClCH2 Cl (B) CH3 CHCl2 (C) CH3 COCl (D) CH3 CH2 Cl
7. Consider the following bromides: [AIEEE 2010]
The correct order of SN 1 reactivity is

(A) A > B > C (B) B > C > A (C) B > A > C (D) C > B > A
8. 2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields:

[JEE MAIN 2016]
(A) (a) and (b) (B) All of these

(C) (a) and (c) (D) (c) only
APNI KAKSHA 22
9. The product of the reaction given below is: [JEE MAIN 2016]
(A) (B) (C) (D)
10. The reaction of propene with HOCl(Cl2 + H2 O) proceeds through the intermediate:
[JEE MAIN 2016]
(A) CH3 − CHCl − CH2+ (B) CH3 − CH + − CH2 − OH
(C) CH3 − CH + − CH2 − Cl (D) CH3 − CH(OH) − CH2+
11. The increasing order of the reactivity of the following halides for the SN 1 reaction is:
[JEE MAIN 2017]
(A) (III) < (II) < (I) (B) (II) < (I) < (III)
(C) (I) < (III) < (II) (D) (II) < (III) < (I)
12. Which of the following, upon treatment with tert-BuONa followed by addition of bromine
water, fails to decolourize the colour of bromine? [JEE MAIN 2017]
(A) (B)
(C) (D)
APNI KAKSHA 23
13. 3-Methyl-pent-2-ene on reaction with HBr in presence of peroxide forms an addition
product.The number of possible stereoisomers for the product is :- [JEE MAIN 2017]
(A) Six (B) Zero (C) Two (D) Four
14. The major product obtained in the following reaction is :- [JEE MAIN 2017]
(A) (±)C6 H5 CH(Ot Bu)CH2 C6 H5 (B) C6 H5 CH = CHC6 H5

(C) (+)C6 H5 CH(Ot Bu)CH2 C6 H5 (D) (−)C6 H5 CH(O𝑡 Bu)CH2 C6 H5
15. The major product formed in the following reaction is [JEE MAIN 2018]
(A) (B)
(C) (D)
16. The major product of the following reaction is: [JEE MAINS 2018]
(A) (B)
(C) (D)
APNI KAKSHA 24
(A) (B)
(C) (D)
18. The increasing order of nucleophilicity of the following nucleophiles is : [JEE MAIN-2019]
⊖
(a) CH3 COΘ2 (b) H2 O (c) CH3 SOΘ
3 (d) O H
(A) (b) < (c) < (d) < (a) (B) (b) < (c) < (a) < (d)
(C) (a) < (d) < (c) < (b) (D) (d) < (a) < (c) < (b)
19. Increasing rate of 𝑆𝑁 𝑙 reaction in the following compounds is: [JEE MAIN-2019]
(A) (B) < (A) < (C) < (D) (B) (A) < (B) < (C) < (D)
(C) (B) < (A) < (D) < (C) (D) (A) < (B) < (D) < (C)
20. The major product 'Y' in the following reaction is: [JEE MAIN-2019]
(A) (B) (C) (D)
APNI KAKSHA 25
21. The major product of the following addition reaction is: [JEE MAIN-2019]
Cl2 /H2 O
H3 C − CH = CH2 ⟶
(A) (B)
(C) (D)
22. An 'Assertion' and a 'Reason' are given below. Choose the correct answer form the following
options: [JEE MAIN-2019]
Assertion (A): Vinyl halides do not undergo nucleophilic substitution easily.
Reason (R): Even though the intermediate carbocation is stabilized by loosely held 𝜋-electrons,
the cleavage is difficult because of strong bonding.
(A) (A) is a correct statement but (R) is a wrong statement.
(B) Both (A) and (R) are correct statements but (R) is not the correct explanations of (A).
(C) Both (A) and (R) are wrong statements
(D) Both (A) and (r) are correct statements and (R) is the correct explanation of (A).
23. Which one of the following is likely to give a precipitate with AgNO3 solution?
[JEE MAIN-2019]
(A) (CH3 )3 CCl (B) CCl4 (C) CHCl3 (D) CH2 = CH − Cl
24. What will be the major product when m-cresol is reacted with propargyl bromide
(HC ≡ C − CH2 Br) in presence of K 2 CO3 in acetone? [JEE MAIN-2019]
(A) (B)
(C) (D)
APNI KAKSHA 26
25. Heating of 2-chloro-1-phenylbutane with EtOK/EtOH gives X as the major product. Reaction of
X with Hg(OAc)2 /H2 O followed by NaBH4 gives Y as the major product. Y is:[JEE MAIN-2019]
(A) (B)
(C) (D)
(A) (B)
(C) (D)
27. Which one of the following alkenes when treated with HCl yields majorly an anti Markovnikov
product? [JEE MAIN-2019]
(A) F3 C − CH = CH2 (B) H2 N − CH = CH2
(C) CH3 O − CH = CH2 (D) Cl − CH = CH2
(A) CH3 CD(I)CHD(Cl) (B) CH3 CD(Cl)CHD(I)

(C) CH3 CD2 CH(Cl)(I) (D) CH3 C(I)(Cl)CHD2
APNI KAKSHA 27
(A) (B) (C) (D)
30. The major products A and B for the following reactions are, respectively: [JEE MAIN-2019]
(A)
(B)
(C)
(D)
31. Increasing order of reactivity of the following compounds for SN 1 substitution is:
[JEE MAIN-2019]
(A) B < A < D < C (B) B < C < A < D (C) B < C < D < A (D) A < B < D < C
APNI KAKSHA 28
32. The major product the following reaction is: [JEE MAIN-2019]
(A) (B)
(C) (D)
(A) (B)
(C) (D)
(A) (B) (C) (D)
APNI KAKSHA 29
(A) (B) (C) (D)
36. Which of the following compounds will produce a precipitate with AgNO3 ?[JEE MAIN-2019]
(A) (B) (C) (D)
37. The major product obtained in the following conversion is:- [JEE MAIN-2019]
(A) (B)
(C) (D)
APNI KAKSHA 30
(A) (B)
(C) (D)
(A) CH3 CH = CHCH2 NH2 (B) CH3 CH = C = CH2

(C) (D) CH3 CH2 C ≡ CH
(A) (B)
(C) (D)
APNI KAKSHA 31
41. The major product the following conversion is: [JEE MAIN-2019]
(A)
(B)
(C)
(D)
42. [JEE MAIN-2020]
Compound X will be:
(A) (B) (C) (D)
43. The correct order of reactivity of the given chlorides with acetate in acetic acid is:
[JEE MAIN-2021]
APNI KAKSHA 32
(A)
(B)
(C)
(D)
44. [JEE MAIN-2021]
The product " A " and "B" formed in above reactions are
APNI KAKSHA 33
45. The product formed in the first step of the reaction of [JEE MAIN-2021]
with excess Mg/Et 2 O(Et = C2 H5 ) is:
(A)
(B)
(C)
(D)
46. The major product (P) in the reaction [JEE MAIN-2022]
[Ph is −C6 H5 ] is
(A) (B)
(C) (D)
APNI KAKSHA 34
47. [JEE MAIN-2022]
In the above reaction ‘A’ is
(A) (B) (C) (D)
48.
The stable carbocation formed in the above reaction is: [JEE MAIN-2022]
(A) (B) (C) (D)
49. Decreasing order towards 𝑆𝑁 1 reaction for the following compounds is:
[JEE MAIN-2023]
(A) a > c > d > b (B) a > b > c > d

(C) b > d > c > a (D) d > b > c > a
APNI KAKSHA 35
50. The correct order of melting point of dichlorobenzenes is [JEE MAIN-2023]
(A) (B)
(C) (D)
APNI KAKSHA 36
EXERCISE # IV (JEE ADVANCE-OBJECTIVE)
1. Chlorination of toluene in the presence of light and heat followed by treatment with aqueous
NaOH gives: [IIT 1990]
(A) o-cresol (B) p-cresol (C) 2,4-dihydroxytoluene (D) Benzoic acid
2. Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl
halides due to [IIT 1990]
(A) The formation of less stable carbonium ion
(B) Resonance stabilization
(C) The inductive effect
(D) sp2 hybridised carbonattached to the halogen
3. 1-Chlorobutane on reaction with alcoholic potash gives: [IIT 1990]

(A) 1-butene (B) 1-butanol (C) 2-butene (D) 2-butanol
4. The products of reaction of alcoholic AgNO2 with ethyl bromide are [IIT 1991]
(A) Ethane (B) Ethyl nitrite (C) Nitroethane (D) Ethyl alcohol
5. Arrange the following compounds in order of increasing dipole moment [IIT 1996]
Toluene m-dichlorobenzene o-dichlorobenzene p-dichlorobenzene
I II III IV
(A) I < IV < II < III (B) IV < I < II < III (C) IV < I < III < II (D) IV < II < I < III
6. (CH3 )3 CMgCl reaction with D2 O produces: [IIT 1997]

(A) (CH3 )3 CD (B) (CH3 )3 OD (C) (CD3 )3 CD (D) (CH3 )3 OD
7. Benzyl chloride (C6 H5 CH2 Cl) can be prepared from toluene by chlorination with:[IIT 1998]
(A) SO2 Cl2 (B) SOCl2 (C) Cl2 , (hv) (D) NaOCl
8. The order of reactivity of the following alkyl halides for a SN 2 reaction is: [IIT 2000]
(A) R-F > R-C > R-Br > R-I (B) R − F > R − Br > R − Cl > R − I
(C) R-Cl > R −Br > RF > RI (D) R-I > RBr > R-Cl > R-F
APNI KAKSHA 37
9. Which of the following has the highest nucleophilicity? [IIT 2000]
(A) F − (B) OH − (C) CH3− (D) NH2−
10. AnSN 2 reaction at an asymmetric carbon of a compound always gives. [IIT 2001]
(A) an enantiomer of the substance
(B) a product with opposite optical rotation
(C) a mixture of diasteremoers
(D) a single stereoisomer
11. The compound that will react most readily with NaOH to form methanol is [IIT 2001]
(A) (CH3 )4 N+ I− (B) CH3 OCH3 (C) (CH3 )3 S+ I− (D) (CH3 )3 Cl
12. Identify the set of reagents / reaction conditions ' X ' and ' Y ' in the following set of
transformation: [IIT 2002]
(A) X = dilute aqueous NaOH, 20∘ C; Y = HBr/ acetic acid, 20∘ C

(B) X = concentrated alcoholic NaOH, 80∘ C; Y = HBr/ acetic acid 20∘ C
(C) X = dilute aqueous NaOH, 20∘ C; Y = Br2 /CHCl3 , 0∘ C
(D) X = concentrated alcoholic NaOH, 80∘ C; Y = Br2 /CHCl3 , 0∘ C
13. CH3 MgBr + Ethyl ester → which can be formed as product. [IIT 2003]
excess
(A) (B)
(C) (D)
APNI KAKSHA 38
14. The product of following reaction is [IIT 2003]
(A) C6 H5 OC2 H5 (B) C2 H5 OC2 H5 (C) C6 H5 OC6 H5 (D) C6 H5 I
15. The following compound on hydrolysis in aqueous acetone will give: [IIT 2005]
It mainly gives
(A) K and L (B) Only K (C) L and M (D) Only M
16. Match the following: [IIT 2006]

Column-I Column-II
(A) CH3 − CHBr − CD3 on treatment with alc. KOH gives CH2 = CH − (A) E1 reaction
CD3 as a major product.
(B) Ph − CHBr − CH3 reacts faster than Ph − CHBr − CD3 . (B) E2 reaction
(C) Ph − CD2 − CH2 Br on treatment with C2 H5 OD/C2 H5 O− gives Ph − (C) E1cb reaction
CD = CH2 as the major product.
(D) PhCH2 CH2 Br and PhCD2 CH2 Br react with same rate. (D) First order
reaction
APNI KAKSHA 39
17. The major product of the following reaction is [IIT 2008]
(A) (B)
(C) (D)
18. In the reaction the products are [IIT 2010]
(A) (B)
(C) (D)
19. KI in acetone, undergoes SN 2 reaction with each of P, Q, R and S. The rates of the reaction vary
as [IIT 2013]
(A) P > Q > R > S (B) S > P > R > Q (C) P > R > Q > S (D) R > P > S > Q
APNI KAKSHA 40
20. The reactivity of compound Z with different halogens under appropriate conditions is given
below [IIT 2014]
The observed pattern of electrophilic substitution can be explained by [IIT 2014]

(A) The steric effect of the halogen
(B) The steric effect of the tert-butyl group
(C) The elctronic effect of the phenolic group
(D) The electronic effect of the turt-butyl group
21. In the following reaction, the major product is [IIT 2015]
(A) (B) (C) (D)
22. The correct statement(s) for the following addition reactions is (are) [IIT 2017]
(A) (M and O) and ( N and P) are two pairs of diastereomers

(B) Bromination proceeds through trans-addition in both the reactions
(C) O and P are identical molecules
(D) (M and O) and (N and P) are two pairs of enantiomers
APNI KAKSHA 41
23. For the following compounds, the correct statement(s) with respect to nucleophilic
substitution reactions is (are) [IIT 2017]
(A) Compound IV undergoes inversion of configuration

(B) The order of reactivity for I, III and IV is: IV > I > III
(C) I and III follow SN 1 mechanism
(D) I and II follow SN 2 mechanism
24. The major product formed in the following reaction of [IIT 2021]
(A)
(B)
(C)
(D)
APNI KAKSHA 42
25. In the following reactions, P, Q, R, and S are the major products. [IIT 2023]
The correct statement about P, Q, R, and S is:

(A) P is a primary alcohol with four carbons.
(B) Q undergoes Kolbe's electrolysis to give an eight-carbon product.
(C) R has six carbons and it undergoes Cannizzaro reaction.
(D) S is a primary amine with six carbons.
APNI KAKSHA 43
EXERCISE # V (JEE ADVANCE-SUBJECTIVE)
1. Fill in the blanks:
(a) Butane nitrile can be prepared by heating _______ with alcoholic KCN. [IIT 1992]
(b) Amongst three isomers of nitrophenol, the one that is least soluble in water is _______
2. Arrange the following in order of their

(i) Increasing basicity
H2 O, OH − , CH3 OH, CH3 O−
(ii) Increasing reactivity in nucleophilic substitution reactions
CH3 F, CH3 I, CH3 Br, CH3 Cl [IIT 1992]
3. Write the structures of the major organic product expected from each of the following
reactions: [IIT 1992]
(i) (ii)
4. Identify the major product in the following reaction. [IIT 1993]
5. Identify the major product in the following reactions: [IIT 1993]
(i) (ii) C6 H5 COOH + CH3 Mgl →? +?
6. Aryl halides are less reactive than alkyl halides towards nucleophilic reagents. Give reason.
[IIT 1994]
APNI KAKSHA 44
7. Draw the stereochemical structure of product in the following reaction. [IIT 1994]
8. Optically active 2 -iodobutane on treatment with NaI in acetone gives a product which does not
show optical activity. Explain briefly. [IIT 1995]
9. An alkyl halide X of formula C6 H13 Cl on treatment with potassium tertiary butoxide gives two
isomeric alkenes Y and Z(C6 H12 ). Both alkenes on hydrogenation give 2,3-dimethylbutane.
Predict the structures of X, Y and Z. [IIT 1996]
10. Predict the structure of the intermediates/products in the following reaction sequence-
[IIT 1996]
11. Which of the following is the correct method for synthesising methyl-t-butyl ether and why?
(CH3 )3 CBr + NaOMe ⟶ or CH3 Br + NaO − t − Bu ⟶ [IIT 1997]
12. Write the structures of the products: [IIT 1998]
C6 H5 CH2 CHClC6 H5
13. (a)
(b) [IIT 1998]
APNI KAKSHA 45
14. Complete the following reaction with appropriate structures of products/reagents. [IIT 1998]
15. What would be major product? [IIT 2000]
16. Identify X, Y and Z in the following synthetic scheme and write their structures [IIT 2002]
17. Give major products A, B, C and D in following reaction sequence. [IIT 2004]
18. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane

using alcoholic KOH is [IIT 2011]
19. The maximum number of isomers (including stereoisomers) that are possible on
monochlorination of the following compounds, is [IIT 2011]
APNI KAKSHA 46
ANSWER KEY
EXERCISE # I (MAINS ORIENTED)
1. A 2. B 3. B 4. C 5. A 6. C 7. A
8. C 9. B 10. C 11. B 12. C 13. A 14. C
15. A 16. D 17. C 18. B 19. B 20. C 21. C
22. D 23. A 24. B 25. A 26. ABCD 27. D 28. B
29. C 30. B 31 C 32. C 33. A 34. B 35. A
36. A 37. D 38. C 39. C 40. C 41. B 42. B
EXERCISE # II-A
1. ABCD 2. BD 3. ABCD 4. AC 5. AD 6. B
7. AC 8. D 9. AC 10. ABD 11. ABCD 12. AD
13. ABCD 14. ABC 15. CD 16. ABCD 17. C
EXERCISE # II-B
1. C 2. C
3. (A) → P, R; (B)→P, Q; (C)→P; (D)→P, Q
4. (A)→Q; (B)→P; (C)→S; (D)→R
5. (A)→S; (B)→Q; (C)→R; (D)→ P
6. (A)→S; (B)→R, S; (C)→R; (D)→P, Q
7. (A)→ P,Q,R,S; (B)→P,R; (C)→T; (D)→Q,S;
8. (A)→Q, S; (B)→P,R,S; (C)→P,R,S; (D)→P,Q,R,S
9.
APNI KAKSHA 47
10. The elimination of HI (or DI) in presence of strong base shows E2 elimination. The rate
determining step involves breaking up of C − H (or C − D ) bond. The C − D bond being
stronger than C − H and thus elimination is faster in case of CH3 − CH2 I.
11.
12. Not available.
13.
EXERCISE # III (JEE MAIN)

1. C 2. A 3. A 4. B 5. D 6. B 7. B
8. B 9. C 10. C 11. B 12. A 13. D 14. B
15. A 16. C 17. B 18. D 19. A 20. D 21. B
22. A 23. A 24. D 25. D 26. B 27. A 28. D
29. B 30. A 31. A 32. D 33. C 34. A 35. B
36. D 37. D 38. B 39. D 40. D 41. D 42. D
43. A 44. C 45. C 46. C 47. C 48. C 49. C
50. D
EXERCISE # IV (JEE-ADVANCE-OBJECTIVE)
1. D 2. BD 3. A 4. C 5. B 6. A 7. AC
8. D 9. C 10. D 11. A 12. B 13. D 14. B
15. A 16. (A)−Q;(B)−Q; (C)−R, S; (D)−P, S
17. A 18. D 19. B 20. ABC 21. D 22. AB
23. (ACD) or (ABCD) 24. B 25. B
APNI KAKSHA 48
(ORGANIC CHEMISTRY) CARBONYL COMPOUND
EXERCISE # I
Q.1 Arrange these compounds in decreasing order of reactivity for the nucleophilic attack.
(I) Acid chloride (II) Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below:
(A) I > II > III > IV (B) IV > III > II > I (C) III > II > I > IV (D) I > IV > II > III
Q.2 In the given reaction
[X] Will be:
(A) HCHO (B)
(C) (D) HCN

Q.3 In the given reaction:
[X] will be:

(A) Only syn oxime (B) Only anti oxime
(C) Mixture of syn and antioxime (D) Secondary amide
Q.4 In the reaction:
[X] Will be:
(A) (B)
(C) (D)
Q.5 Number of aldol products (without counting stereoisomers) in the given reaction:
⊖
OH
C6 H5 CHO + CH3 − CHO ⟶ Product
will be:
(A) One (B) Three (C) Two (D) Four
APNI KAKSHA 1
Q.6 In the given reaction
(X) and (Y) will respectively be :

(A) CH3 − CH2 − CHO and CH3 − CH2 − CHO
(B) CH3 − CHO and CH3 − CH2 − CHO
(C) CH3 − CHO and CH3 − CHO
(D) CH3 − CHO and
Q.7 Acetophenone can be obtained by the distillation of :

(A) (C6 H5 COO)2 Ca (B) (CH3 COO)2 Ca
(C) (C6 H5 COO)2 Ca and (CH3 COO)2 Ca (D) (C6 H5 COO)2 Ca and (HCOO)2 Ca
Q.8 Gem dihalide on hydrolysis gives :
(A) Vic diol (B) Gem diol (C) Carbonyl compound (D) Carboxylic acid
Q.9 Acetal or ketal is:
(A) Vic dialkoxy compound (B) α, ω-dialkoxy compound
(C) α-alkoxy alcohol (D) Gem dialkoxy compound
Q.10 In the given reaction :
[X] will be :
(A) CH3 − COOC2 H5 (B) CH3 − CH2 − COOC2 H5
(C) Br − CH2 − COOC2 H5 (D)
Q.11 Cross cannizzaro reaction is example of :

(A) Redox reaction (B) Disproportionation
(C) Both (A) and (B) (D) Only oxidation
Q.12 Acetaldehyde can be converted into by which reagent ?
(A) KOH (B) KOH followed by LAH

(C) excess of HCHO and KOH (D) KCN followed by SBH
APNI KAKSHA 2
Q.13 Product of Perkin reaction is :
(A) α, β-unsaturated aldehyde (B) β-cyclohexyl α, β-unsaturated aldehyde
(C) β-Aryl- α, β-unsaturated acid (D) All of these
Q.14 Which one of the combinations will give propanaldehyde on dry distillation?
(A) (C6 H5 COO)2 Ca and (HCOO)2 Ca
(B) (CH3 COO)2 Ca and (CH3 CH2 − COO)2 Ca
(C) (CH3 − CH2 − COO)2 Ca and (HCOO)2 Ca
(D) (CH3 COO)2 Ca and (CH3 COO)2 Ca
[X] will be:

(A) Methyl oxide (B) Phorone (C) 1,3, 5-Trimethylbenzene (D) 2-Butyne
Q.16 In the reaction sequence:
→ ( X ) ⎯⎯⎯⎯ → ( Y ) ⎯⎯⎯⎯
( ii ) H2O/Zn→ ( Z )
() 3
hv/Cl2 alc.KOH/  i O
Cyclohexane ⎯⎯⎯
(Z) will be:

(A) Hexanal (B) 2-Hexanone (C) 3-Hexanone (D) Hexanedial
Q.17 Grignard reagents can never give carbonyl compounds with:
(A) CO2 (B) RCOCl (C) RCN (D) RCOOR
Q.18 The given reaction:
() i Zn
C6H5 − CHO + Br − CH2 − COOC2H5 ⎯⎯⎯⎯⎯ →C6H5 − CH = CH − COOC2H5
(ii)HOH/NH4Cl
(iii)
is known as :
(A) Perkin reaction (B) Knoevenagel reaction
(C) Reformatsky reaction (D) Claisen-Schmidt reaction
Q.19 The product of the reaction:
Will be:
(A) C6 H5 − CH = CH − COOH (B)
(C) (D)
APNI KAKSHA 3
Q.20 Cyanohydrin of which compound on hydrolysis will give lactic acid?
(A) C6 H5 CHO (B) HCHO (C) CH3 CHO (D) CH3 − CH2 − CHO
(X) and (Y) are:
(A)
(B)
(C)
(D)
Q.22 Acetaldehyde cannot give :

(A) Iodoform test (B) Lucas test (C) Benedict test (D) Tollens test
Q.23 Compound formed by the reaction of furfural with ethanol
is :
(A) an aldol (B) an acetal (C) a ketal (D) a hemiacetal
Q.24 The reaction in which NaCN/C2 H5 OH/HOH is used is :
(A) Perkin reaction (B) Benzoin condensation
(C) Reimer-Tieman reaction (D) Rosenmunds reduction
Q.25 A compound with molecular formula C8 H18 O4 does not give litmus test and does not give colour
with 2,4-DNP. It reacts with excess MeCOCl to give a compound whose vapour density is 152.
Compound A contains how many hydroxy groups?
(A) 1 (B) 2 (C) 3 (D) 4
Q.26 In the reaction sequence:
(C H O)
→( X ) ⎯⎯⎯⎯ →( Y )
KHSO1 / Al
CH2OH − CHOH − CH2OH ⎯⎯⎯ ⎯ 2 5 3

(Y) will be:

(A) CH2 = CH − CHO
(B) CH2 = CH − CH2 OH
(C) Mixture of CH2 = CH − COOH and CH2 = CH − CH2 OH
(D)
APNI KAKSHA 4
Q.27 Tollen's reagent is used for the differentiation between:
(A) HCHO and CH3 CHO
(B) CH3 COCH3 and CH3 CHO
(C)
(D) HCHO and C6 H5 CHO
Q.28
Identify relationship between A & B products?

(A) Diastereoisomers (B) Enantiomers (C) Positional isomer (D) Identical
Q.29 In the reaction sequence
The product (B) is:
(A) (B) (C) (D)
Q.30 In the reaction
The product (A) is:
(A) (B) (C) (D)
Q.31 Which of the following does not form a stable hydrate by the addition of H2 O ?
(A) (B)
(C) (D)
APNI KAKSHA 5
Q.32 The conversion
Can be effected by using the reagent
(A) Tollen’s reagent (B) O2 (C) (D)
The major product is:
(A) (B)
(C) CH2 = CH − COOCH3 (D) CH3 CH(CN)COCH3
Q.34 (I) (II)
Organic product P & Q are respectively –
(A) (B)
(C) (D)
Q.35 The major product obtained in the reaction is
(A) (B) (C) (D)
Q.36 Total number of stereoisomers of major product (Q) are:

CH3 − CHO + 4HCHO ⎯⎯⎯⎯
NaOH
− HCOONa
→ ( P ) ⎯⎯⎯⎯
2CH3 −CHO
H
→ (Q )
(A) 0 (B) 4 (C) 8 (D) 2
APNI KAKSHA 6
Q.37 CH3 CHO + NH2 OH → CH3 CH = N − OH
The above reaction occurs satisfactorily at
(A) pH = 1 (B) pH = 4.5 (C) pH = 12 (D) any value of pH
Q.38 An organic compound (A), C5 H10 O, reacts with hydrazine to form a hydrazone derivative (B).
The hydrazone (B) on being heated with KOH at about 180∘ C, gives n-pentane. The compound
(A) does not respond positively to Tollen's reagent and to the iodoform test. The compound (A)
is
(A) (B) (C) (D)
Q.39 The compound having the highest dipole moment is:
(A) (B) (C) (D)
Q.40
(A) (B) (C) (D)
Question No. 41 to 43 (3 questions)

An alkene (A) C16 H16 on ozonolysis gives only product (B) C8 H8 O. (B) also can be obtained by
hydrolysis of the product obtained by reaction between cyano benzene and CH3 MgBr. (A) can
show geometrical isomerism and it can decolourise Br2 water. (B) on treatment with SeO2
produces (C)
Q.41 Which is not correct about (A)?
(A) A is optically inactive
(B) On catalytic hydrogenation 'trans' form of A produces racemic mixture
(C) A can be prepared by Witting reaction on acetophenone with Ph3 P = C(CH3 )Ph.
(D) On treatment with per acid followed by hydrolysis 'trans' form of A produces racemic
mixture
Q.42 Which is not correct about B ?
(A) It gives iodoform test
(B) On treatment with LiAlH4 , H2 O it produces a compound which also responds to iodoform
test.
(C) It gives Tollen's test
(D) On treatment with NH2 NH2 followed by alc. KOH at high temperature, it produces ethyl
benzene
APNI KAKSHA 7
Q.43 Which is not correct about C ?
(A) On treatment with NaBH4 it will produce a diol.
(B) On treatment with OH − (conc.) followed by acidification racemic mixture of a carboxylic
acid is obtained
(C) It gives Tollen's test
(D) It can take part in aldol condensation
Question No.44 to 48 (5 questions)

Compound 'C' was prepared in a three step sequence from ethyl
trifluoroacetate.
The first step in a sequence involved treating ethyl trifluoroacetate with NH3 to give a
compound A. A on treatment with reagent ' X ' (alongwith gentle heating) produces a
compound B (which on hydrolysis can produce an acid). B on treatment with an orango metallic,
' Y ', followed by hydrolysis produces C. Based on above passing attempt the following
questions:
Q.44 Structutre of 'A' would be
(A) (B)
(C) (D)
Q.45 Structure of B would be
(A) (B) CF3 − C ≡ N (C) CF3 − CH2 − CN (D) CF3 − CH2 − NH2
Q.46 'X' should be
(A) BaO2 (B) H2 O2 (C) P4 O10 (D) N2 O
Q.47 When 'C' is treated with perbenzoic acid it will produce
(A) (B)
(C) (D) (CH3 )3 C − OH
APNI KAKSHA 8
Q.48
(A) (B)
(C) (D)
(Question No. 49 & 50)

Questions given below consist of two statements each printed as Assertion (A) and Reason (R);
while answering these questions you are required to choose any one of the following four
responses:
(A) If both (A) and (R) are true and (R) is the correct explanation of (A)
(B) If both (A) and (R) are true but (R) is not correct explanation of (A)
(C) If (A) is true but (R) is false
(D) If (A) is false and (R) is true
Q.49 Assertion : Benzaldehyde with HCN gives two isomeric compounds
Reason : Both nitrile and isonitrile compounds are possible when HCN reacts with carbonyl
group.
Q.50 Assertion:
Reason: There are no α − H in this compound, so it can't give aldol.
APNI KAKSHA 9
EXERCISE # II
Q.1 Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by :
(A) I2 /NaOH (B) NaSO3 H (C) NaCN/HCl (D) 2,4-DNP
Q.2 An optically inactive alcohol (A) C6 H12 O is oxidized by MnO2 to produce optically inactive
carbonyl compound while reduction of (A) by H2 /Ni produces optically active compound.
Possible structure(s) of alcohol is/are
(A) Hex-2-ene-1-ol (B) Hex-3-ene-2-ol
(C) 2-Methyl pent-2 - ene-1-ol (D) 3-Methyl pent-2 - ene-1-ol
Q.3 Consider the structure of given alcohol:
This alcohol can be prepared from:
(A) (B)
(C) (D)
Q.4 Correct option(s) regarding following reaction sequence is/are :

HgSO4 Ba (OH )
CH3C  CH ⎯⎯⎯
H2SO4
→ P ⎯⎯⎯

2
→Q ⎯⎯⎯
NaOH
I2
→ R + S ⎯⎯
6Ag
→T
'x'
(A) T is homologue of ' X ' (B) R is sodium salt of
(C) P can produce S with NaOI (D) R is sodium salt of
Q.5 Which of the following compounds will not give aldol condensation:
(A) Acetaldehyde (B) Formaldehyde (C) Pivaldehyde (D) Crotonaldehyde
Q.6 (A)
In above reaction (A) and (B) will respectively be
(A) (B)
(C) (D)
Q.7 Stability of hydrates of carbonyl compounds depends on:

(A) Steric hindrance (B) Presence of -I group on gemdiol carbon
(C) Intramolecular hydrogen bonding (D) angle strain in carbonyl compound
APNI KAKSHA 10
Q.8 Which of the following can be used for protection of carbonyl group
(A) CH2 OH − CH2 OH/H ⊕ (B) CH2 OH − CH2 − CH2 OH/H ⊕
(C) HS − (CH2 )3 − SH (D) CH2 OH − CH2 − CHO
Q.9 Which of the following is/are example of 1,4-addition reaction
(A)
(B)
(C)
(D)
Q.10 Which of the following(s) will form stable hemiketal:
(A)
(B)
(C)
(D)
Q.11 Mixture of Ph − CHO&HCHO is treated with NaOH then Cannizzaro reaction involves:
(A) Oxidation of HCHO (B) Reduction of HCHO
(C) Oxidation of Ph − CHO (D) Reduction of Ph − CHO
Q.12 Final product in the given reaction sequence is:
(A) (B)
(C) (D)
APNI KAKSHA 11
Q.13 Consider the following reaction sequence.
The products (A) and (B) are, respectively,
(A) (B)
(C) (D)
Q.14 Consider the following sequence of reactions.
The products (A) and (B) are, respectively.
(A) (B)
(C) (D)
The major product (B) is:
(A) (B) (C) (D)
APNI KAKSHA 12
NaOH
(CH3 )2 CHNO2 + HCHO ⟶
the major product is
(A) (CH3 )2 CHCH2 ONO2 (B)
(C) (D)
The ketone (A) is:
(A) (B) (C) (D)
the product (X) is:
(A) (B)
(C) (D)
Q.19
End product (B) of above reaction is:
APNI KAKSHA 13
(A) (B)
(C) (D)
Q.20
Final Product ‘S’ is –

OH OH OH
OH
(A) (B)
HO
HO HO HO
OH
(C) (D)
Q.21 Which of the following reactions will give(s) 2∘ alcohol as a major product:
(A)
(B)
(C)
(D)
APNI KAKSHA 14
Q.22 Match list-I with list-II
List-I List-II
Θ
OH Θ
(A) C6 H5 CHO + HCHO ⟶ C6 H5 CH2 OH + HCOO (P) Cannizzaro reaction
(B) (Q) Aldol condensation
(C) (R) Soda-lime Decarboxylation
(D) (S) Benzil benzilic acid rearragement
Q.23 Match list-I with list-II

List – I List – II
NaBH4
(A) CH2 = CH − CHO ⎯⎯⎯ → (P) Acetal

(B) C6H5CHO + Ph − NH2 ⎯⎯
H
→ (Q) Schiff's base

(C) C6H5COCH3 + CH3 − CH2 − NH2 ⎯⎯
H
→ (R)

(D) RCHO + 2RCH2OH ⎯⎯
H
→ (S) Imine
APNI KAKSHA 15
EXERCISE # III
Q.1 Predict the product of the reaction of propanal with each of the following :
(a) Methylmagnesium iodide, followed by dilute acid.
(b) Sodium acetylide, followed by dilute acid
(c) Phenyllithium, followed by dilute acid.
(d) Methanol containing dissolved hydrogen chloride
(e) Ethylene glycol, p-toluenesulfonic acid, benzene
(f) Aniline (C6 H5 NH2 )
(g) Dimethylamine, p-toluenesulfonic acid, benzene
(h) Hydroxylamine
(i) Hydrazine
(j) Product of part (i) heated in triethylene glycol with sodium hydroxide
(k) p-Nitrophenylhydrazine
(l) Semicarbazide
(m) Sodium cyanide with addition of sulfuric acid
(n) Chromic acid
Q.2 Give structure for the products of the reaction when butanal is treated with each of the
following reagents
(a) [Ag(NH3 )2 ]OH then HOH/H ⊕
⊖
(b) O H/HOH, Δ
(c) NH2 OH/H ⊕
(d) C6 H5 Li then HOH
⊖
(e) C6 H5 CHO, O H, Δ
(f) CH ≡ CNa then HOH/H ⊕
(g) CH2 OH − CH2 OH, H ⊕
(h) SH − CH2 − CH2 − CH2 − SH then Raney Ni/H2
(i) CH3 MgBr then H2 O
(j) HCN
(k) NaBH4
(j)
APNI KAKSHA 16
Q.3 Column – I Column – II
(A) (P) Formation of six member ring takes place
(B) (Q) Final product is Ketone
(C) (R) Final product formed will give positive

Idoform test
(D) (S) Final product formed will react with 2,4-
DNP. (2,4-Di-nitrophenyl hydrazine)
Q.4 Arrange the following compounds in decreasing order of K eq. for hydrate formation.
(A) C6 H5 COCH3 (B)
(C) (D)
Paragraph for Q. 05 to 06
Two reactions which are example of nucleophilic attack are given as below.
Reaction-I:
Reaction-II:
Q.5 Value of x is:

(A) x ≤ 4.5 (B) x = 6 (C) x > 7 (D) Can't decide
Q.6 Value of y is:
(A) x = 4.5 (B) x = 1.5 (C) x = 7 (D) x = 9
Q.7 Some Grignard reagents react with ethyl orthoformate, followed by acidic hydrolysis, to give
aldehydes. Propose mechanisms for the two steps in this synthesis.
APNI KAKSHA 17
Q.8 A synthesis that begins with 3,3-dimethyl-2-butanone gives the epoxide shown. Suggest
reagents appropriate for each step in the synthesis.
Q.9 Predict the organic products:
Paragraph for Q.No.10 to 11

A (Hydrocarbon )(C ⇒ 88.24%) [Molecular weight of A = 68 ]
( ii ) n −propylbromide→ B ( C8H14 )
()i Na
A ⎯⎯⎯⎯⎯⎯
→C5H6O(C )
2+
A ⎯⎯⎯Hg
⎯
dil.H2SO4
KMnO4
A ⎯⎯⎯
H+
→ Carboxylic acid + Gas
Q.10 'A' can be:

(A) H3 C − H2 C − C ≡ C − CH3 (B) CH3 − CH2 − CH2 − C ≡ C − H
(C) CH3 —CH —C  CH (D)

|
CH3
Q.11 Correct statement reagarding C is.

(A) C reacts with fehling solution to give red ppt.
(B) C gives +ve iodoform test
(C) C give -ve 2, 4, D.N.P test
(D) C is aldehyde
Q.12
'B' is:
APNI KAKSHA 18
(A) (B)
(C) (D) CH3 − COONa
Q.13 Identify A to E:
Q.14 Show how you would accomplish the following syntheses efficiently and in good yield. You may
use any necessary reagents.
Identify the lettered compounds in the following reaction shceme. Compounds F, G and K are
isomers of molecular formula C13 H18 O. How could 1
H NMR spectroscopy distinguish these
three compounds from each other?
Q.15 Identify 'K' product?
(A) (B) (C) (D)
Q.16 Identify 'G' product?
(A) (B) (C) (D)
APNI KAKSHA 19
In given reaction sequence
17. Alkene A is:
(A) (B) (C) (D)
18.
(A) 1 (B) 2 (C) 3 (D) 4
APNI KAKSHA 20
EXERCISE # IV (MAINS)
Q.1 When CH2 = CH − COOH is reduced with LiAlH4 , the compound obtained will be –
[AIEEE-2003]
(A) CH3 − CH2 − CH2 OH (B) CH3 − CH2 − CHO
(C) CH3 − CH2 − COOH (D) CH2 = CH − CH2 OH
Q.2 Which one of the following undergoes reaction with 50% sodium hydroxide solution to give the
corresponding alcohol and acid ? [AIEEE-2004]
(A) Phenol (B) Benzaldehyde (C) Butanal (D) Benzoic acid
Q.3 Which one of the following is reduced with Zn − Hg/HCl to give the corresponding hydrocarbon
[AIEEE-2004]
(A) Butan-2-one (B) Acetic acid (C) Acetamide (D) Ethyl acetate
Q.4 On mixing ethyl acetate with aqueous sodium chloride, the composition of the resultant
solution is [AIEEE-2004]
(A) CH3 COOC2 H5 + NaCl (B) CH3 COONa + C2 H5 OH
(C) CH3 COCl + C2 H5 OH + NaOH (D) CH3 Cl + C2 H5 COONa
Q.5 The best reagent to convert pent-3-en-2-ol into pent -3 -en −2 − one is - [AIEEE-2005]
(A) Acidic dichromate (B) Acidic permanganate
(C) Pyridinium chloro-chromate (D) Chromic anhydride in glacial acetic acid
Q.6 Rate of the reaction-
is fastest when X is -
(A) NH2 (B) Cl (C) OCOR (D) OC2 H5
Q.7 Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH
is- [AIEEE-2006]
(A) CH3 CH2 CH(OH)CH2 CH3 (B) C6 H5 CH2 CH2 OH
(C) (D) PhCHOHCH3
P+ I2 H2O
Q.8 In the following sequence of reactions CH3CH2OH ⎯⎯→ A ⎯⎯⎯
Mg
Ether
→ B ⎯⎯⎯
HCHO
→C ⎯⎯ → D then
compound 'D' is – [AIEEE-2007]

(A) Butanal (B) n-Butyl alcohol (C) n-Propyl alcohol (D) Propanal
Q.9 In the following sequence of reactions, the alkene affords the compound 'B' :- [AIEEE-2008]
O3 H2O
CH3CH = CHCH3 ⎯⎯ → A ⎯⎯
Zn
→B
The compound B is
(A) CH3 CH2 CHO (B) CH3 COCH3 (C) CH3 CH2 COCH3 (D) CH3 CHO
APNI KAKSHA 21
Q.10 Bakelite is obtained from phenol by reacting with [AIEEE-2008]
(A) (CH2 OH)2 (B) CH3 CHO (C) CH3 COCH3 (D) HCHO
Q.11 Which of the following on heating with aqueous KOH, produces acetaldehyde ? [AIEEE-2009]
(A) CH2 ClCH2 Cl (B) CH3 CHCl2 (C) CH3 COCl (D) CH3 CH2 Cl
Q.12 In Cannizzaro reaction given below :- [AIEEE-2009]

2PhCHO ⎯⎯
:OH
→ PhCH2OH + PhCO2
the slowest step is :-
(A) The abstraction of proton from the carboxylic group
(B) The deprotonation of PhCH2 OH
⊖
(C) The attack of : OH at the carboxyl group
(D) The transfer of hydride to the carbonyl group
Q.13 One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a
molecular mass of 44u. The alkene is :- [AIEEE-2010]
(A) Ethene (B) Propene (C) 1-Butene (D) 2-Butene
Q.14 Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms
the presence of :- [AIEEE-2011]
(A) An isopropyl group (B) An acetylenic triple bond
(C) Two ethylenic double bonds (D) A vinyl grou
Q.15 Ozonolysis of an organic compound 'A' produces acetone and propionaldehyde in equimolar
mixture. Identify 'A' from the following compounds : - [AIEEE-2011]
(A) 2-Methyl - 1- pentene (B) 1-Pentene
(C) 2-Pentene (D) 2-Methyl-2-pentene
Q.16 Trichloroacetaldehyde was subjected to Cannizzaro's reaction by using NaOH. The mixture of
the products contains sodium trichloroacetate and another compound. The other compound is:
[AIEEE-2011]
(A) 2,2,2-Trichloropropanol (B) Chloroform
(C) 2,2,2-Trichloroethanol (D) Trichloromethanol
Q.17 Silver Mirror test is given by which one of the following compounds? [AIEEE-2011]
(A) Formaldehyde (B) Benzophenone (C) Acetaldehyde (D) Acetone
Q.18 In the given transformation, which of the following is the most appropriate reagent ?
[AIEEE-2012]
⊖
(A) NaBH4 (B) NH2 NH2 , O H (C) Zn − Hg/HCl (D) Na, Liq. NH3
APNI KAKSHA 22
Q.19 Iodoform can be prepared from all except :- [AIEEE-2012]
(A) Isobutyl alcohol (B) Ethyl methyl ketone
(C) Isopropyl alcohol (D) 3-Methyl-2-butanone
Q.20 A compound with molecular mass 180 is acylated with CH3 COCl to get a compound with
molecular mass 390. The number of amino groups present per molecule of the former
compound is :- [JEE(Main)-2013]
(A) 2 (B) 5 (C) 4 (D) 6
Q.21 The major organic compound formed by the reaction of 1,1,1-trichloroethane with silver
powder is :- [JEE(Main)-2014]
(A) 2-Butyne (B) 2-Butene (C) Acetylene (D) Ethene
Q.22 The most suitable reagent for the conversion of R − CH2 − OH → R − CHO is :-
[JEE(Main)-2014]
(A) CrO3 (B) PCC (Pyridinium chlorochromate)
(C) KMNO4 (D) K 2 Cr2 O7
Q.23 A compound A with molecular formula C10 H13 Cl gives a white precipitate on adding silver
nitrate solution. A on reacting with alcoholic KOH gives compound B as the main product. B on
ozonolysis gives C and D. C gives Cannizaro reaction but not aldol condensation. D gives aldol
condensation but not Cannizaro reaction. A is : [JEE(Main)-2015]
(A) (B)
(C) C6H5 − CH2 − CH2 − CH2 − CH2 − Cl (D) C6H5 − CH2 − CH2 − CH − CH3
|
Cl
Q.24 In the reaction sequence [JEE(Main)-2015]
the product B is:-

(A) CH3 − CH = CH − CHO (B) CH3 − CH2 − CH2 − CH3
(C) CH3 − CH2 − CH2 − CH2 − OH (D)

Q.25 Which compound would give 5-keto-2-methyl hexanal upon ozonolysis?
[JEE(Main) 2015]
(A) (B) (C) (D)
APNI KAKSHA 23
Q.26 The correct sequence of reagents for the following conversion will be: [JEE(Main) 2017]
(A) CH3 MgBr, [Ag(NH3 )2 ]+ OH − , H + /CH3 OH

(B) [Ag(NH3 )2 ]+ OH − , CH3 MgBr, H + /CH3 OH
(C) [Ag(NH3 )2 ]+ OH − , H + /CH3 OH, CH3 MgBr
(D) CH3 MgBr, H + /CH3 OH, [Ag(NH3 )2 ]+ OH −
Q.27 The major product formed in the following reaction is: [JEE MAIN-2019]
(A) (B)
(C) (D)
Q.28 In the following reaction [JEE MAIN-2019]
Aldehyde + alcohol ⎯⎯ → Acetal
HCl
Aldehyde Alcohol
HCHO tBuOH
CH3CHO MeOH
The best combinations is :
(A) CH3 CHO and t BuOH (B) HCHO and t BuOH
(C) CH3 CHO and MeOH (D) HCHO and MeOH
Q.29 cannot be prepared by : [JEE MAIN-2019]
(A) PhCOCH3 + CH3 CH2 MgX (B) PhCOCH2 CH3 + CH3 MgX
(C) HCHO + PhCH(CH3 )CH2 MgX (D) CH3 CH2 COCH3 + PhMgX
APNI KAKSHA 24
Q.30 In the following reactions, products A and B are: [JEE MAIN-2019]
(A)
(B)
(C)
(D)
Q.31 The increasing order of the reactivity of the following with LiAlH4 is: [JEE MAIN-2019]
(A) (A) < (B) < (C) < (D) (B) (A) < (B) < (D) < (C)
(C) (B) < (A) < (C) < (D) (D) (B) < (A) < (D) < (C)
Q.32 The aldehydes which will not form Grignard product with one equivalent Grignard reagents
are: [JEE MAIN-2019]
(A) (B), (C) (B) (B), (C), (D) (C) (C), (D) (D) (B), (D)
APNI KAKSHA 25
Q.33 Major products of the following reaction are: [JEE MAIN-2019]
(A) (B) CH3 OH and HCO2 H
(C) (D)
Q.34 But-2-ene on reaction with alkaline KMnO4 at elevated temperature followed by acidification
will give: [JEE MAIN-2019]
(A) one molecule of CH3 CHHOO and one molecule of CH3 COOH
(B) 2 molecules of CH3 CHO
(C) 2 molecules of CH3 COOH
(D) CH3 − CH − CH − CH3
| |
OH OH
Q.35 An organic compound neither reacts with neutral ferric chloride solution moor with Fehling
solution. It however, reacts with Grignard reagent and gives positive iodoform test. The
compound is : [JEE MAIN-2019]
(A) (B)
(C) (D)
Q.36 The major product of the following reaction is : [JEE MAIN-2019]
(A) (B) (C) (D)
APNI KAKSHA 26
Q.37 The major product obtained in the following reaction is : [JEE MAIN-2019]
(A) (B) (C) (D)
HCl
Q.38 In the following reaction carbonyl compound +MeOH ⇌ acetal. Rate of the reaction is the
highest for : [JEE MAIN-2019]
(A) Acetone as substrate and methanol in excess
(B) Acetone as substrate and methanol in stoichiometric amount
(C) Propanal as substrate and methanol in excess
(D) Propanal as substrate and methanol in stoichiometric amount.
( ) ( ) 3
1 NaBH ( ) ( ) 2
2 PBr ( )
3 Mg/Ether 4 CO 5 H
Q.39 Hex-3-ynal ⎯⎯⎯⎯ 4
→⎯⎯⎯ →⎯⎯⎯⎯ →⎯⎯⎯ →⎯⎯⎯ → (X), formed product X will be:
[JEE MAIN 2020]
(A) (B)
(C) (D)
Q.40
What will be the major product? [JEE MAIN 2020]
(A) (B)
(C) (D)
APNI KAKSHA 27
Q.41
Predict the compound (P) on the basis of above sequence of the reactions? [JEE MAIN 2020]
(A) (B)
(C) (D)
Q.42 The increasing order of the following compounds towards HCN addition is
[JEE MAIN 2020]
(i) (ii)
(iii) (iv)
(A) (iii) < (iv ) < (ii ) < ( i ) (B) (iii) < (i) < (iv) < (ii)
(C) (iii) < (iv ) < (i) < (ii) (D) (i) < (iii) < (iv) < (ii)
Q.43 The increasing order of the reactivity of the following compounds in nucleophilic addition
reaction is Propanal, Benzaldehyde, Propanone, Butanone [JEE MAIN 2020]
(A) Propanal < Propanone < Butanone < Benzaldehyde
(B) Benzaldehyde < Propanal < Propanone < Butanone
(C) Benzaldehyde < Butanone < Propanone < Propanal
(D) Butanone < Propanone < Benzaldehyde < Propanal
Q.44 The compound A in the following reactions is [JEE MAIN 2020]

( i) CH3MgBr/H2O ( i ) O3
A. ⎯⎯⎯⎯⎯⎯
→
( ii) Conc.H2SO4 / B. ⎯⎯⎯⎯
→C + D
( ii) Zn/H2O
C.
D.
(A) (B)
(C) (D)
APNI KAKSHA 28
Q.45 Consider the following reactions [JEE MAIN 2020]
'A' ⎯⎯⎯⎯
ozonolysis
→ 'B'+ 'C'
(C6H14 )
(A) (B)
(C) (D)
Q.46 Given below are two statements : [JEE MAIN 2021]

Statement I : The nucleophilic addition of sodium hydrogen sulphite to an aldehyde or a ketone
involves proton transfer to form a stable ion.
Statement II : The nucleophilic addition of hydrogen cyanide to an aldehyde or a ketone yields
amine as final product.
In the light of the above statements, choose the most appropriate answer from the options given
below :
(A) Both Statement I and Statement II are true.
(B) Statement I is true but Statement II is false.
(C) Statement I is false but Statement II is true.
(D) Both Statement I and Statement II are false.
Q.47 For the reaction given below : [JEE MAIN 2021]
The compound which is not formed as a product in the reaction is a :

(A) compound with both alcohol and acid functional groups
(B) monocarboxylic acid
(C) dicarboxylic acid
(D) diol
APNI KAKSHA 29
Q.48 The structures of A and B formed in the following reaction are: [JEE MAIN 2021]
[Ph = −C6 H5 ]
(A) (B)
(C) (D)
Q.49 The structure of the starting compound P used in the reaction given below is: [JEE MAIN 2021]
(A) (B) (C) (D)
Q.50
Which among the above compound/s does/do not form Silver mirror when treated with
Tollen's reagent? [JEE MAIN 2021]
(1) (I), (III) and (IV) only (2) Only (IV)
(3) Only (II) (4) (III) and (IV) only
APNI KAKSHA 30
Q.51 The major product (P) in the following reaction is : [JEE MAIN 2021]
(A) (B) (C) (D)
Q.52 [JEE MAIN 2021]
In the above chemical reaction, intermediate " X " and reagent/condition " A " are:
(A) (B)
(C) (D)
Q.53 Which of the following is least basic? [JEE MAIN 2021]

(A) (CH3 CO)N̈HC2 Hs (B) (C2 H5 )3 N̈
¨
(C) (CH3 CO)2 NH (D) (C2 H5 )2 N̈ H
Q.54 Hoffmann bromomide degradation of benzamide gives product A, which upon heating with
CHCl3 and NaOH gives product B. The structures of A and B are : [JEE MAIN 2021]
(A) (B)
(C) (D)
APNI KAKSHA 31
Q.55 Primary, secondary and tertiary amines can be separated using :- [JEE MAIN 2021]
(A) Para-Toluene sulphonyl chloride (B) Chloroform and KOH
(C) Benzene sulphonic acid (D) Acetyl amide
Q.56 C7 H7 N2 OCl + C2 H3 OH → [O + N2 + X + ′′ Y ′′
′′ ′′
(A) In the above reaction, the structural formula of [JEE MAIN 2021]
(A) (B)
(C) (D)
Q.57
Considering the above reaction, X and Y respectively are [JEE MAIN 2021]
(A)
(B)
(C)
(D)
APNI KAKSHA 32
Q.58
Consider the above chemical reaction and identify product "A" [JEE MAIN 2021]
(A) (B)
(C) (D)
Q.59 In the reaction of hypobromite with amide, the carbonyl carbon is lost as : [JEE MAIN 2021]
(1) CO2−
3 (2) HCO−
3 (3) CO2 (4) CO
Q.60 Which of the following is an example of Conjugated diketone? [JEE MAIN 2022]
(A) (B)
(C) (D)
Q.61
Consider the above reaction sequence and identify the product B. [JEE MAIN 2022]
(A) (B) (C) (D)
Q.62 Which will have the highest enol content? [JEE MAIN 2022]
(A) (B) (C) (D)
APNI KAKSHA 33
Q.63 The correct structure of product ' A ' formed in the following reaction. [JEE MAIN 2022]
(A) (B) (C) (D)

Q.64 ' R ' formed in the following sequence of reaction is: [JEE MAIN 2023]
(A) (B)
(C) (D)
Q.65 Number of compounds giving (i) red colouration with ceric ammonium nitrate and also (ii)
positive iodoform test from the following is _______. [JEE MAIN 2023]
APNI KAKSHA 34
Q.66 [JEE MAIN 2023]
List-I List-II
(Reaction) (Reagents)
(A) Hoffmann Degradation (I) Conc. KOH,
(B) Clemenson reduction (II) CHCl3,NaOH/H3O+
(C) Cannizaro reaction (III) Br2, NaOH
(D) Reimer-Tiemann (IV) Zn-Hg/HCl
reaction
(A) (A) − III, (B) − IV, (C) − II, (D) − I
(B) (A) − II, (B) − IV, (C) − I, (D) − III
(C) (A) − III, (B) − IV, (C) − I, (D) − II
(D) (A) − II, (B) − I, (C) − III, (D) − IV
Q.67 Which of the following compounds would give the following set of qualitative analysis ?
[JEE MAIN 2023]
(i) Fehling's Test : Positive
(ii) Na fusion extract upon treatment with sodium nitroprusside gives a blood red colour but
not
(A) (B)
(C) (D)
Q.68 Cyclohexylamine when treated with nitrous acid yields (P). On treating (P) with PCC results in
(Q). When (Q) is heated with dil. NaOH we get (R) The final product (R) is : [JEE MAIN 2023]
(A) (B)
(C) (D)
APNI KAKSHA 35
Q.69 The structures of major products A, B and C in the following reaction are sequence.
[JEE MAIN 2023]
(A) (B)
(C) (D)
APNI KAKSHA 36
EXERCISE-IV # (A) (OBJECTIVE QUESTIONS)
Q.1 The formation of cyanohydrin from a ketone is an example of: [IIT 1990]
(A) Electrophilic addition (B) Nucleophilic addition
(C) Nucleophilic substitution (D) Electrophilic substitution
Q.2 The enolic form of acetone contains: [IIT 1990]
(A) 9 sigma bonds, 1 pi bond and 2 lone pairs
(B) 8 sigma bonds, 2 pi bonds and 2 lone pairs
(C) 10 sigma bonds, 1 pi bond and 1 lone pair
(D) 9 sigma bonds, 2 pi bonds and 1 lone pair
Q.3 m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives:
[IIT 1991]
(A) Potassium m-chlorobenzoate and m-hydroxybenzaldehyde
(B) m-hydroxybenzaldehyde and m-chlorobenzyl alcohol
(C) m-chlorobenzyl and m-hydroxybenzyl alcohol
(D) Potassium m-chlorobenzoate and m-chlorobenzyl alcohol
Q.4 Hydrogenation of benzoyl chloride in the presence of Pdd and BaSO4 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
Q.5 An organic compound C3 H6 O does not give a precipitate with 2,4-Dinitrophenyl hydrazine
reagent and does not react with metallic sodium. It could be: [IIT 1993]
(A) CH3 CH2 CHO (B) CH3 COCH3
(C) CH2 = CH − CH2 OH (D) CH2 = CH − O − CH3
Q.6 Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
[IIT 1995]
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane
Q.7 In the Cannizzaro reaction given below, 2Ph − CHO 2 the slowest
Ph − CH2 OH + PhCO−
step is: [IIT 1996]
(A) The attack of OH − at the carbonyl group
(B) The transfer of hydride to the carbonyl group
(C) The abstraction of proton from the carboxylic acid
(D) The deprotonation of Ph − CH2 OH
Q.8 Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group
is : [IIT 1997]
(A) MeCOCl (B) MeCHO (C) MeCOOMe (D) MeCOOCOMe
APNI KAKSHA 37
Q.9 In a Cannizzaro reaction the intermediate which is the best hydride donor is: [IIT 1997]
(A) (B)
(C) (D)
Q.10 CH3 CHO + H2 NOH ⟶ CH3 − CH = N − OH. The above reaction occurs at: [IIT 1997]
(A) pH = 1 (B) pH = 4.5 (C) Any value of pH (D) pH = 12
Q.11 Among the following compounds, which will react acetone to give a product containing
>C=N− [IIT 1998]
(A) C6 H5 NH2 (B) (CH3 )3 N (C) C6 H5 NHC6 H5 (D) C6 H5 NHNH2
Q.12 The product obtained via oxymercuration (HgSO4 − H2 SO4 ) of 1-butyne would be
[IIT 1998]
(A) (B) CH3 CH2 CH2 CHO

(C) CH3 CH2 CHO + HCHO (D) CH3 CH2 COOH + HCOOH
Q.13 Which of the following will undergo aldol condensation: [IIT 1998]
(A) Acetaldehyde (B) Propanaldehyde
(C) Benzaldehyde (D) Trideutero acetaldehyde
Q.14 Which of the following will react with water: [IIT 1998]
(A) CHCl3 (B) Cl3 CCHO (C) CCl4 (D) ClCH2 CH2 Cl
Q.15 A new carbon-carbon bond formation is possible in [IIT 1998]
(A) Cannizzaro reaction (B) Friedel-Crafts alkylation
(C) Clemmensen reduction (D) Reimer-Tiemann reaction
Q.16 Which of the following has the most acidic hydrogen: [IIT 2000]
(A) 3-hexanone (B) 2,4-hexanedione
(C) 2,5-hexanedione (D) 2,3-hexandione
Q.17 A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
[IIT 2001]
(A) benzyl alcohol and sodium format
(B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium format
(D) benzyl alcohol and methyl alcohol
APNI KAKSHA 38
Q.18 1-propanol & 2-propanol can be best distinguished by : [IIT 2001]
(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acidic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2 SO4 followed by reaction with Fehling solution
Q.19 Compound A (molecular formula C3 H8 O ) is treated with acidified potassium dichromate to
form a product B (molecular formula C3 H6 O ). B forms a shining silver mirror on warming with
ammonical silver nitrate. B when treated with an aqueous solution of H2 NCONHNH2 . HCl and
sodium acetate gives a product C. Identify the structure of C. [IIT 2002]
(A) CH3 CH2 CH = NNHCONH2 (B)
(C) (D) CH3 CH2 CH = NCONHNH2
Q.20
any one of the products formed is :
(A) (B)
(C) (C)
Q.21 Products formed by P & Q can be differentiated by:
[IIT 2003]
(A) 2, 4 DNP (B) Lucas reagent (ZnCl2 ) conc. HCl
(C) NaHSO3 (D) Fehlings solution
APNI KAKSHA 39
Q.22 The order of reactivity of phenyl Magnesium Bromide with the following compounds is
[IIT 2004]
(A) II > III > I (B) I > III > II

(C) II > I > III (D) All react with the same rate
Q.23 [IIT 2004]

What is X ?
(A) CH3 COOH (B) BrCH2 , COOH (C) (CH3 CO)2 O (D) CHO − COOH
Q.24 The smallest ketone and its next homologue are reacted with NH2 OH to form oxime.
[IIT 2006]
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active
Q.25 Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E.
Compound E on further treatment with aqueous KOH yields compound F. Compound F is
[IIT 2007]
(A) (B) (C) (D)
Q.26 Statement-1 : Glucose gives a reddish-brown precipitate with Fehling's solution.

because
Statement-2 : Reaction of glucose with Fehling's solution gives CuO and gluconic acid.
[IIT 2007]
(A) Statement- 1 is True, Statement- 2 is True; Statement- 2 is a correct explanation for
Statement-1.
Statement-1.
(D) Statement-1 is False, Statement- 2 is True.
APNI KAKSHA 40
Q.27 Match the compounds/ion in column I with their properties/ reaction in Column II. Indicate
your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS.
[IIT 2007]
Column I Column II
(A) C6 H5 CHO (P) gives precipitate with 2,4-dinitrophenylhydrazine
(B) CH3 C ≡ CH (Q) gives precipitate with AgNO3
(C) CN − (R) is a nucleophile
(D) I − (S) is involved in cyanohydrin formation
Paragraph for Question No. 28 to 30

A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to
compounds J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound
L, whereas K on reaction with KOH gives only M.
Q.28 Compound H is formed by the reaction of [IIT 2008]
(A) (B)
(C) (D)
Q.29 The structure of compound 𝐈 is [IIT 2008]
(A) (B) (C) (D)
Q.30 The structures of compounds J, K and L, respectively, are [IIT 2008]

(A) PhCOCH3 , PhCH2 COCH3 and PhCH2 COO− K +
(B) PhCHO, PhCH2 CHO and PhCOO− K +
(C) PhCOCH3 , PhCH2 CHO and CH3 COO− K +
(D) PhCHO, PhCOCH3 and PhCOO− K +
APNI KAKSHA 41
Paragraph for Question Nos. 31 to 33
A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr
followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R,
which undergoes intramolecular aldol reaction to give predominantly S.
1.MeMgBr 1.O 1.OH−→ s

P ⎯⎯⎯⎯⎯→ Q ⎯⎯⎯⎯⎯3 → R ⎯⎯⎯⎯
2.H+ ,H O 2.Zn,H O
2
2.
2
3.H SO ,
2 4
Q.31 The structure of the carbonyl compound P is [IIT 2009]
(A) (B) (C) (D)
Q.32 The structure of the products Q and R, respectively, are [IIT 2009]
(A) (B)
, ,
(C) (D)
, ,
Q.33 The structure of the product 𝐒 is [IIT 2009]
(A) (B)
(C) (D)
APNI KAKSHA 42
Paragraph for Questions Nos. 34 to 35
An acyclic hydrocarbon P, having molecular formula C6 H10, gave acetone as the only organic
product through the following sequence of reactions, in the which Q is an intermediate organic
compound.
Q.34 The structure of compound P is - [IIT 2011]

(A) CH3 CH2 CH2 CH2 − C ≡ C − H (B) H3 CH2 C ≡ C − CH2 CH3
(C) (D)
Q.35 The structure of the compound Q is - [IIT 2011]
(A) (B)
(C) (D)
Q.36 The number of aldol reaction(s) that occurs in the given transformation is [IIT 2012]
(A) 1 (B) 2 (C) 3 (D) 4

Q.37 Among P, Q, R and S, the aromatic compound(s) is / are : [IIT 2013]
(A) P (B) Q (C) R (D) S
APNI KAKSHA 43
Q.38 After completion of the reactions (I and II), the organic compound(s) in the reaction mixtures
is(are) [IIT 2013]
(A) Reaction I: P and Reaction II : P

(B) Reaction I : U, acetone and Reaction II : Q acetone
(C) Reaction I : T, U, acetone and Reaction II : P
(D) Reaction I : R, acetone and Reaction II : S acetone
Q.39 The major product in the following reaction is [IIT 2014]
(A) (B)
(C) (D)
Q.40 The major product of the following reaction is - [IIT 2015]
(A) (B)
(C) (D)
APNI KAKSHA 44
Q.41 In the following reactions, the product S is - [IIT 2015]
(A) (B)
(C) (D)
Q.42 Positive Tollen's test is observed for: [IIT 2016]
(A) (B) (C) (D)

Q.43 The major product of the following reaction sequence is : [IIT 2016]
(A) (B)
(C) (D)
Q.44 Compound P and R upon ozonolysis produce Q and S, respectively. The molecular formula of Q
and S is C8 H8 O. Q undergoes Cannizzaro reaction but not haloform reaction, where S undergoes
haloform reaction but not Cannizzaro reaction. [IIT JEE 2017]
The option(s) with suitable combination of P and R, respectively, is (are)
APNI KAKSHA 45
(A)
(B)
(C)
(D)
Q.45 The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is (are) [IIT JEE 2018]
(A) (B)
(C) (D)
Q.46 The desired product X can be prepared by reacting the major product of the reactions in LIST-I
with one or more appropriate reagents in LIST-II.
(given, order of migratory aptitude: aryl > alkyl > hydrogen) [IIT JEE 2018]
APNI KAKSHA 46
List-I List-II
P. 1. I2 , NaOH
Q. 2. [Ag(NH3 )2 ]OH
R. 3. Fehling solution
S. 4. HCHO, NaOH
5. NaOBr
The correct option is
(A) P → 1; Q → 2,3; R → 1,4; S → 2,4 (B) P → 1,5; Q → 3,4; R → 4,5; S → 3
(C) P → 1,5; Q → 3,4; R → 5; S → 2,4 (D) P → 1,5; Q → 2,3; R → 1,5; S → 2,3
Q.47 Choose the correct option(s) for the following set of reactions [IIT JEE 2019]
(A) (B)
(C) (D)
APNI KAKSHA 47
Q.48 In the reaction scheme shown below, Q, R, and S are the major products. [IIT JEE 2020]
The correct structure of
Q.49 Correct option(s) for the following sequence of reactions is(are)
(A) Q = KNO2, W = LiAlH4 (B) R = benzenamine, V = KCN

(C) Q = AgNO2, R = phenylmethanamine (D) W = LiAlH4, V = AgCN
APNI KAKSHA 48
Q.50 In the following reactions, P, Q, R and S are the major products.
The correct statement(s) about 𝐏, 𝐐, 𝐑, and 𝐒 is(are)

(A) Both 𝐏 and 𝐐 have asymmetric carbon(s).
(B) Both 𝐐 and 𝐑 have asymmetric carbon(s).
(C) Both 𝐏 and 𝐑 have asymmetric carbon(s).
(D) 𝐏 has asymmetric carbon(s), 𝐒 does not have any asymmetric carbon.
APNI KAKSHA 49
EXERCISE-IV # (B) (SUBJECTIVE QUESTIONS)
Q.1 NaOC2H5 inabsolute
C6H5 − CHO + CH3 − COOC2H5 ⎯⎯⎯⎯⎯⎯
C2H5OHandheat
→(D) [IIT 1995]
Q.2 [IIT 1996]

Q.3 Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric
oximes. Write structures of the oximes. [IIT 1997]
Q.4 An aldehyde (A) (C11 H8 O), which does not undergo self aldol condensation, gives benzaldehyde
and two mole of (B) on ozonolysis. Compound (B), on oxidation with silver ion, gives oxalic acid.
Identify the compounds (A) and (B). [IIT 1998]
Q.5 [IIT 1998]

Q.6 What would be the major product in each of the following reaction? [IIT 2000]
Q.7 Identify (A), (B) and (C), and give their structures. [IIT 2000]
Q.8 Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8 H8 O2

were given for identification. Based on the following observations, give structure of the
compounds. [IIT 2002]
(i) Both A and B form a silver mirror with Tollen's reagent; also, B gives a positive test with
FeCl3 solution.
(ii) C gives positive iodoform test.
(iii) D is readily extracted in aqueous NaHCO3 solution.
(iv) E on acid hydrolysis gives 1,4-dihydroxybenzene.
Q.9
( A ) ⎯⎯⎯⎯
ozonolysis
→( F ) + (G ) ⎯⎯⎯
NaOH
→HCOONa + 1ºalcohol
(D) is isomer of A. E gives negative test with Fehling solution but gives iodoform test F and G
gives Tollen's test but do not give iodoform test. Identify A to G. [IIT 2003]
APNI KAKSHA 50
ANSWER KEY
EXERCISE # I
1. (A) 2. (B) 3. (C) 4. (D) 5. (C) 6. (B) 7. (C)
8. (C) 9. (D) 10. (C) 11. (A) 12. (C) 13. (C) 14. (C)
15. (C) 16. (D) 17. (A) 18. (C) 19. (D) 20. (C) 21. (C)
22. (B) 23. (D) 24. (B) 25. (C) 26. (D) 27. (B) 28. (A)
29. (B) 30. (C) 31. (D) 32. (D) 33. (B) 34. (C) 35. (C)
36. (D) 37. (B) 38. (C) 39. (B) 40. (A) 41. (D) 42. (C)
43. (D) 44. (B) 45. (B) 46. (C) 47. (A) 48. (C) 49. (C)
50. (D)
EXERCISE # II
1 (A,B) 2 (C,D) 3 (A,B,C)4 (A,B,C) 5 (B,C) 6 (A,B)
7 (A,B,C,D) 8 (A,B,C) 9 (A,C,D) 10 (B,C,D) 11 (A,D) 12 (D)
13 (C) 14 (C) 15 (D) 16 (B) 17 (B) 18 (C)
19 (B) 20 (B) 21 (A,B,C)22 (A) → P, (B) → Q, (C) → S, (D) → R
23 (A) R, (B) Q,S, (C) S, (D) P
EXERCISE # III
1. (a) (b)
(c) (d)
(e) (f) CH3 − CH2 − CH = NH − Ph
(g) (h) CH3 − CH2 − CH = N − OH

(i) CH3 − CH2 − CH = N − NH2 (j) CH3 − CH2 − CH2
(k) p-Nitro phenyl hydrazon (l) Semi carbazone
(m) (n) CH3 − CH2 − CO2 H
Q.2 (a) (b)
APNI KAKSHA 51
(c) C − C − C − C = N − OH (d)
(e) (f)
(g) (h) C − C − C − C
(i) 2∘ alcohol (j) Cyanohydrine (k) 1∘ alcohol
(l)
Q.3 Ans. (A)P,Q,S;(B)P,Q,S;(C)P,Q,S;(D)P,Q,S

Q.4 Ans. 3 > 2 > 1 > 4 Q.5 Ans.(C) Q.6 Ans. (A)
Q.7 Ans.
Q.8 Ans. H + /Br2 ; H2 /Ni; NaOH
Q.9 Ans. (a) (b)
(c)
Q.10 Ans. (B,C) Q.11 Ans. (B) Q.12 Ans. (B) Q.13
Q.14
(d) (i) H2 , Ni (e) NH2 NH2 /H2 O2 (f) NaBH4

Q.15 Ans. (A) Q.16 Ans. (D) Q 17. Ans. (B) Q.18 Ans. (D)
APNI KAKSHA 52
EXERCISE # IV (MAINS)
1. (4) 2. (2) 3. (1) 4. (2) 5. (4) 6. (2) 7. (4)
8. (3) 9. (4) 10. (4) 11. (2) 12. (4) 13. (4) 14. (4)
15. (4) 16. (3) 17. (1, 3) 18. (2) 19. (1) 20. (2) 21. (1)
22. (2) 23. (2) 24. (1) 25. (4) 26. (3) 27. (2) 28. (4)
29. (3) 30. (1) 31. (2) 32. (4) 33. (3) 34. (3) 35. (1)
36. (3) 37. (3) 38. (3) 39. (A) 40. (A) 41. (B) 42. (B)
43. (D) 44. (C) 45. (B) 46. (B) 47. (A) 48. (A) 49. (A)
50. (C) 51. (B) 52. (C) 53. (C) 54. (B) 55. (A) 56. (A)
57. (B) 58. (C) 59. (A) 60. (C) 61. (A) 62. (C) 63. (A)
64. (B) 65. (C) 66. (C) 67. (D) 68. (B) 69. (D)
EXERCISE # IV - A (OBJECTIVE QUESTIONS)

1 (B) 2 (A) 3 (D) 4 (B) 5 (D) 6 (D) 7 (B)
8 (A) 9 (D) 10 (B) 11 (A,D) 12 (A) 13 (A,B,D) 14 (B)
15 (B,D) 16 (B) 17 (A) 18 (C) 19 (A) 20 (C) 21 (D)
22 (C) 23 (C) 24 (B) 25 (A) 26 (C)
27 (A) P,S; (B) Q; (C) Q,R,S; (D) Q,R 28 (B) 29 (A) 30 (D) 31 (B)
32 (A) 33 (B) 34 (D) 35 (B) 36 (C) 37 (A,B,C,D) 38. (C)
39 (D) 40 (A) 41 (A) 42 (A,B,C) 43. (A) 44 (A, B) 45 (A, B,D)
46. (D) 47. (A,B) 48. (B, D) 49. (C,D) 50. (C,D)
49.
Therefore, correct options are
Q = AgNO2, R = phenylmethanamine
W = LiAlH4, V = AgCN
APNI KAKSHA 53
EXERCISE - IV # B (SUBJECTIVE QUESTIONS)
1. C6 H5 CH = CHCOOC2 H5 , CH3 − CH = CH − COOC2 H5
2.
3.
4.
5. 6.
7.
8.
9.
APNI KAKSHA 54
SOLUTION
EXERCISE (JEE-MAIN)
39.
40.
41.
42. Attack of nucleophile on carbonyl centre depends upon

(i) Steric factor (ii) Electronic factor
∴ Rate of reaction should follow the order
(ii) > (iv ) > (i) > (iii)
43. Increasing hindrence and electron relasing group (ERG) attached on carboxyl group decrease
the reactivity.
Correct order of nucleophilic addition reaction is
APNI KAKSHA 55
44.
45.
46. Statement I : Correct
Statement II :
APNI KAKSHA 56
47.
48.
49.
NaOCl is used in haloform reaction as reagent.
APNI KAKSHA 57
50. Aldehydes gives positive Tollen’s test (silver mirror)
51.
52.
53. For the given compounds:
(a)
; L.P. on Nitrogen is delocalised.
(b)
; L.P. on Nitrogen is delocalised.

(c)
; L.P. on Nitrogen is delocalised due to conjugation with both
(Hence least basic)

(d) CH3 − CH2 − N̈H − CH2 − CH3 ; L.P. on Nitrogen is localised.
APNI KAKSHA 58
54.
55. Primary amines react with Para Toluene sulfonyl chloride to form a precipitate that is soluble
in NaOH.Secondary amines reacts with para toluene sulfonyl chloride to give a precipitate that
is insoluble in NaOH. Tertiary amines do not react with para toluen.
56.
57.
APNI KAKSHA 59
58.
59.
60. is a conjugated diketone
61. Although Acetyl Acetone predominantly gives Acid base reaction with G.R due to Active
methylene group but according to given option ans should be based on nucleophilic addition
reaction (NAR).
APNI KAKSHA 60
62.
, Which is aromatic in nature.

63. PhCH = O + PhCH = O
PhCH2 OD + PhCO−
2
64.
65.
66. Reactions Reagent used

(A) Hoffmann degradation Br2 /NaOH
(B) Clemenson reduction Zn − Hg/HCl
(C) Cannizaro reaction conc. KOH/Δ
(D) Reimer-Tiemann reaction CHCl3 , NaOH/H3 O+
APNI KAKSHA 61
67. Aromatic aldehydes do not give Fehling's test.. Both nitrogen and sulfur must be present to
obtain blood red colour Sodium nitroprusside gives blood red colour with S & N.
68.
69.
APNI KAKSHA 62
(ORGANIC CHEMISTRY) REDUCTION OXIDATION
EXERCISE # I
1. Tollen's reagent is
(A) 𝐂𝐮𝟐 𝐎 (B) [𝐂𝐮(𝐎𝐇)𝟒 ]𝟐− (C) 𝐀𝐠𝐎𝐇 (D) [𝐀𝐠(𝐍𝐇𝟑 )𝟐 ]+
(A) (B)
(C) (D)
3. Baeyer's reagent decolourises when reacts with:
(A) Alkane (B) Alkene only
(C) Alkene and alkyne both (D) Alkyne only
4. The end products of the reaction are:
(A) (B)
(C) (D) Propane
5. X and Y in following reaction is:

KMnO4 / 
1 − Butyne ⎯⎯⎯⎯ →X + Y
(A) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇 + 𝐎𝟐 (B) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇
(C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇 + 𝐂𝐎𝟐 (D) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐂𝐇𝟑 + 𝐇𝐂𝐎𝐎𝐇
APNI KAKSHA 11
6. Major product of following reaction is/are:
(A) (B)
(C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐎𝐇 (D)

7. Bayer's reagent is:
(A) alkaline permanganate solution (B) acidified permanganate solution
(C) neutral permanganate solution (D) aqueous bromine solution
8. An alkyne 𝐂𝟕 𝐇𝟏𝟐 when reacted with alkaline 𝐊𝐌𝐧𝐎𝟒 followed by acidification by 𝐇𝐂𝐥, yielded a
mixture of &𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐎𝐎𝐇. The alkyne is –
(A) 3-hexyne (B) 2-methyl-2-hexyne

(C) 2-methyl-3-hexyne (D) 3-methyl-2-hexyne
9. 𝐑 𝟏 and 𝐑 𝟐 in following reaction respectively is :
(A) Cold alkaline 𝐊𝐌𝐧𝐎𝟒 , 𝐎𝐬𝐎𝟒 /𝐇𝟐 𝐎𝟐 (B) Cold alkaline 𝐊𝐌𝐧𝐎𝟒 , 𝐇𝐂𝐎𝟑 𝐇&𝐇𝟑 𝐎+
(C) Cold alkaline 𝐊𝐌𝐧𝐎𝟒 , 𝐂𝟔 𝐇𝟓 𝐂𝐎𝟑 𝐇 (D) 𝐂𝟔 𝐇𝟓 𝐂𝐎𝟑 𝐇, 𝐇𝐂𝐎𝟑 𝐇
10. Which of the following is/are hydrocarbon?
(A) 𝐏 (B) 𝐐 (C) 𝐑 (D) 𝐒

11. Glucose as well as fructose are oxidized by periodic acid. The number of moles of 𝐇𝐂𝐎𝐎𝐇
formed from each mole of glucose and fructose are
(A) 5 and 5 (B) 5 and 4 (C) 5 and 3 (D) 4 and 312
APNI KAKSHA 12
12. Major products of the given reaction will be:
(A) (B) (C) (D) Both (B) and (C)
13. Fehlings solution is

(A) 𝐀𝐠𝐍𝐎𝟑 solution +𝐍𝐚𝐎𝐇 solution +𝐍𝐇𝟒 𝐎𝐇
(B) Alkaline solution of Cupric ion complexed with citrate ion
(C) Copper sulphate + sodium potassium tartarate +𝐍𝐚𝐎𝐇
(D) Copper sulphate solution
14. Secondary alcohols on heating with copper at 𝟑𝟎𝟎∘ 𝐂 give
(A) Alkenes (B) Aldehydes (C) Ketones (D) tert-alcohols
15. The reagent which can react easily with both acetaldehyde and acetone is:
(A) Tollens reagent (B) Schiffs reagent (C) 𝐇𝟐 /𝐍𝐢 (D) Fehling's solution
16. Which of the following compounds is resistant to periodic acid oxidation?
(A) (B) (C) (D)

17. Identify (P) and (Q) respectively in the given reaction :
(A) (B)
(C) (D)
APNI KAKSHA 13
18. Which of the following sets of compounds cannot turn clear orange solution of 𝐂𝐫𝐎𝟑 / aq. 𝐇𝟐 𝐒𝐎𝟒
to greenish opaque solution
(A) I, IV (B) II, III (C) I, II (D) III, IV

19. Major product of following reaction is/are:
(A) 𝐑 − 𝐂𝐇𝐎 (B) 𝐑 − 𝐂𝐇𝟐 𝐎𝐇 (C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐎𝐇 (D) 𝐑 − 𝐂𝐎𝐎𝐇
20. Major product is :
(A) (B)
(C) (D)
21. The product which is not formed in the following reaction is:
(A) HCOOH (B) (C) (D)
APNI KAKSHA 14
22. The products of acid hydrolysis of 𝐏 and 𝐐 can be distinguished by:
(A) Lucas reagent (B) 2, 4-DNP (C) Fehling's solution (D) 𝐍𝐚𝐇𝐒𝐎𝟑
23. On catalytic reduction with 𝐇𝟐 /𝐏𝐭 how many alkenes will give 𝐧-butane ?
(A) 1 (B) 2 (C) 3 (D) 4
24. Major products of following reaction will be :
(A) Racemic mixture (B) Diastereomers

(C) Meso (D) Constitutional isomers
25. Alkene 𝐗 in following reaction is :
(A)
(B)
(C)
(D)
26. Which reagent will be used for the given conversion?
(A) 𝐍𝐚/ Liq. 𝐍𝐇𝟑 (B) 𝐇𝟐 , 𝐏𝐝 − 𝐂𝐚𝐂𝐎𝟑 (C) 𝐋𝐢, 𝐏𝐡 − 𝐍𝐇𝟐 (D) 𝐇𝟐 , 𝐏𝐭
APNI KAKSHA 15
27. In following reaction A and B respectively are:
(A)
(B)
(C)
(D)
28. Which of the following will decolorise alkaline 𝐊𝐌𝐧𝐎𝟒 solution?

(A) 𝐂𝟑 𝐇𝟖 (B) 𝐂𝐇𝟒 (C) 𝐂𝐂𝐥𝟒 (D) 𝐂𝟐 𝐇𝟒
29. Product 𝐁 and 𝐂 in given reaction are respectively:
OsO4 HIO4
2 − methylbut − 2 − ene ⎯⎯ ⎯
H2O2
→ A ⎯⎯→ B+C
(A)
(B)
(C)
(D)
30. If the following compound is treated with 𝐏𝐝 in excess of 𝐇𝟐 gas, how many stereoisomers of
the product will be obtained?
(A) 1 (B) 2 (C) 3 (D) 4

APNI KAKSHA 16
(A) (B)
(C) (D) All of these
32. Which of the following can not be obtained when alkenes are oxidised with 𝐊𝐌𝐧𝐎𝟒 and then
followed by acid hydrolysis?
(A) alkanoic acids (B) alkanols (C) alkanones (D) carbon dioxide
33. Which alkyne gives 3 -ethylhexane on catalytic hydrogenation?
(A) (B)
(C) (D)
34. The final major product (𝐁) in following reaction is :
(A) (B) (C) (D)

35. In following reaction if (𝐁) and (𝐂) both give + ve iodoform test then compound (𝐀) can be :
(A) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇 − 𝐎 − 𝐂𝐇𝟐 − 𝐂𝐇𝟑 (B)
(C) (D) 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐎 − 𝐂𝐇𝟐 − 𝐂𝐇𝟑
APNI KAKSHA 17
36. Which of the following can be selectively oxidised by 𝐌𝐧𝐎𝟐 /𝚫 :
(A) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇𝐎𝐇 − 𝐂𝐇𝟑 (B) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇
(C) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇𝟐 − 𝐎𝐇 (D) 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇
37. Which will give silver mirror test with Tollens reagent :
(A) 𝐂𝟔 𝐇𝟓 𝐂𝐇𝐎 (B) 𝐂𝐇𝟑 − 𝐂𝐇𝐎 (C) 𝐇𝐂𝐎𝐎𝐇 (D) 𝐂𝟔 𝐇𝟓 𝐂𝐇(𝐎𝐇)𝐂𝐎𝐂𝟔 𝐇𝟓
38. Fehling solution gives red precipitate with:
(A) Aromatic aldehyde (B) Aliphatic aldehyde
(C) Ketones (D)

39. Choose the major product of the follolwing reaction.
(A) (B)
(C) (D)
40. Silver mirror test with Tollens reagent is given by:

(A) 𝐂𝟔 𝐇𝟓 𝐂𝐇𝐎 (B) 𝐏𝐡 − 𝐍𝐇 − 𝐎𝐇
(C) (D) 𝐂𝐇𝟑 𝐂𝐇𝐎
(A) 𝐏𝐡 − 𝐂𝐇𝟐 𝐎𝐇 (B) 𝐍𝐇𝐌𝐞𝟐 (C) 𝐏𝐡 − 𝐂𝐇𝟐 − 𝐍𝐌𝐞𝟐 (D) 𝐏𝐡 − 𝐂𝐇𝐎
APNI KAKSHA 18
EXERCISE # II
1. In which of the following reactions reactant and product both can show stereoisomerism:
(A) (B)
(C) (D)
2. Which of the following is an example of oxidation reaction:

𝐏𝐂𝐥𝟑 𝐍𝐢/𝐇𝟐
(A) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐎𝐇 ⟶ (B) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇𝟐 ⟶
𝐁𝐫𝟐 𝐃𝐌𝐒𝐎/𝐍𝐚𝐇𝐂𝐎𝟑
(C) 𝐂𝐇𝟑 − 𝐂𝐇 = 𝐂𝐇𝟐 ⟶ (D) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐥 ⟶
𝐂𝐂𝐥𝟒
3. In following reaction sequence compound B is:
CHO
|
(A) CHO (B) 𝐂𝐇𝟑 − 𝐂𝐇𝐎 (C) 𝐂𝐇𝟑 − 𝐂𝐎𝐎𝐇 (D) 𝐇 − 𝐂𝐎𝐎𝐇
4. Major product of which reaction can show Stereoisomerism?

𝐏𝐂𝐂
(A) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇𝟐 − 𝐎𝐇 ⟶
(B)
(C) C6H5 − CH = CH − CH2 − CH − CH2 − OH ⎯⎯⎯⎯⎯

TsCl
DMSO,NaHCO3
→
|
CH3
(D)
APNI KAKSHA 19
5. Which of the following compound will give positive Tollens test
(A) Tartaric acid (B)
(C) CH3CH2CH2CH2CH − OCH3 (D)

|
OH
6. Which of the following reactions is/are correctly match with their major products?
(A) (B)
(C) (D)
7. Which one of the following alcohols are oxidised by 𝐌𝐧𝐎𝟐 ?
(A) 𝐂𝟔 𝐇𝟓 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇 (B)
(C) (D) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − 𝐎𝐇

8. Which will give the Tollen test.
(A) (B) (C) (D)
9. Major product and reactant of which reactions gives positive tollens test:
(A) (B)
HIO4
OHCCH2OH ⎯⎯→
(C) (D) 
APNI KAKSHA 20
10. In following reaction 𝐏 and 𝐐 are respectively.
(A) Acetone and Hexane-1,2,5,6-tetraol.

(B) Acetaldehyde and Acetone.
(C) Acetaldehyde and Hexane-1,2,5,6-tetraol.
(D) Acetone and Formaldehyde.
11. Choose the incorrect option(s) for following sequence.
(A) 𝐏 is a racemic compound (B) Q is terminal alkyne

(C) 𝐗&𝐑 are positional isomer (D) Formation of 𝐑 is redox reaction
12. Which of the following compounds will consume even number of periodic acid?
(A) HO − CH2 − CH2 − CH − CH2 − OH (B) CH2 — CH − CH − CH2
| | | | |
OH OH OH OH OH
(C) H2C — CH − CH − CH3 (D) Me − C − CH − Me
| | | || |
OH OH OH O NH2
13. Which of the following is correctly matched?
(A) (B)
(C) (D)
APNI KAKSHA 21
14.
Column-I (Conversion) Column-II
(Required
Reagent)
(A) (P) 𝐇𝟐 , 𝐏𝐝 − 𝐁𝐚𝐒𝐎𝟒
(B) (Q) Li, Liq. 𝐍𝐇𝟑
(C) 𝐇𝟑 𝐂 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇𝟑 ⟶ 𝐇𝟑 𝐂 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 − (R) 𝐍𝟐 𝐇𝟒 /𝐇𝟐 𝐎𝟐

𝐂𝐇𝟑
(D) (S) 𝐁𝟐 𝐇𝟔 , 𝐂𝐇𝟑 𝐂𝐎𝐎𝐇
15. Total number of alcohols obtained in following reaction is:
16. Total numbers of reagent that can be used for given conversion.
⊖
(a) 𝐙𝐧 − 𝐇𝐠/𝐇𝐂𝐥 (b) 𝐋𝐢𝐀𝐥𝐇𝟒 (c) 𝐋𝐢𝐁𝐇𝟒 (d) ( i )𝐍𝟐 𝐇𝟒 (ii) 𝐎𝐇, 𝚫
(e) 𝐋𝐢𝐀𝐥(𝐎𝐄𝐭)𝟑 𝐇 (f) 𝐑𝐞𝐝 𝐏/𝐇𝐈 (g) (i) (𝐂𝐇𝟐 𝐒𝐇)𝟐 (ii) 𝐇𝟐 , Raney 𝐍𝐢
COMPREHENSION TYPE Paragraph for Q. 17 to 21
17. The compound (𝐂) is:
(A) (B) (C) 𝐄𝐭−≡ −𝐄𝐭 (D) Both (A) and (B)
APNI KAKSHA 22
18. The compound (𝐅) is:
(A) (B) (C) 𝐄𝐭−≡ −𝐄𝐭 (D) Both (A) and (B)
19. The compound (𝐃) is:
(A) (B) (C) (D) Both (B) and (C)
20. The compound (𝐆) is:
(A) (B) (C) (D) None of these

21. The compound (𝐄) is:
(A) (B)
(C) One mole of (𝐀) and one mole of (𝐁) (D) No reaction.
22. Reaction of 2-butanol with 𝐂𝐮, 𝚫 involve
(A) dehydrogenation (B) elimination
(C) dehydration (D) oxidation
23. Which of the following will give syn addition?
(A) (B)
(C) (D)
SUBJECTIVE TYPE
24. Complete the following reactions:
(a) (b) (c)

APNI KAKSHA 23
25. Complete the following reactions:
26. How many alkene on catalytic reduction give normal butane as product.
𝐇𝟐 /𝐏𝐭 𝐇𝟐 /𝐏𝐭 𝐇𝟐 /𝐏𝐭
(i) (A) ⟶ n-butane (ii) (B) ⟶ Iso-pentane (iii) (C) ⟶ Neo-pentane
𝐇𝟐 /𝐏𝐭 𝐇𝟐
(iv) (D) ⟶ Cyclopentane (v) (E) ⟶
𝐏𝐭
27. Give the expected major product for each reaction, including stereochemistry where
applicable.
28. Give product in the following reactions
APNI KAKSHA 24
EXERCISE # III (MAIN & ADVANCE)
1. Hydrogenation of benzoyl chloride in the presence of 𝐏𝐝 and 𝐁𝐚𝐒𝐎𝟒 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
2. Draw the stereochemical structure of the product in the following reactions. [IIT 1994]
H2
R − C  C − R ⎯⎯⎯⎯⎯
Lindlarcatalyst
→
3. Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
[IIT 1995]
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane
4. In the reaction, 𝐏 is [IIT 1995]
(A) 𝐂𝐇𝟑 𝐂𝐎𝐂𝐇𝐎 (B) 𝐂𝐇𝟑 𝐂𝐎𝐎𝐂𝐇𝟑 (C) 𝐂𝐇𝟑 𝐂𝐎𝐂𝐇𝟐 𝐎𝐇 (D) None
5. Which one of the following alkenes will react fastest with 𝐇𝟐 under catalytic hydrogenation
condition [IIT 2000]
(A) (B) (C) (D)

6. The appropriate reagent for the following transformation: [IIT-2000]
(A) 𝐙𝐧(𝐇𝐠), 𝐇𝐂𝐥 (B) 𝐍𝐇𝟐 𝐍𝐇𝟐 , 𝐎𝐇 − (C) 𝐇𝟐 /𝐍𝐢 (D) 𝐍𝐚𝐁𝐇𝟒
7.
Hydrogenation of the above compound in the presence of poisoned paladium catalyst gives-
[IIT-2001]
(A) An optically active compound (B) An optically inactive compound
(C) Aracemic mixture (D) Adiastereomeric mixture
8. When 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐎𝐎𝐇 is reduced with 𝐋𝐢𝐀𝐥𝐇𝟒 , the compound obtained will be –
[AIEEE-2003]
(A) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝟐 𝐎𝐇 (B) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐇𝐎
(C) 𝐂𝐇𝟑 − 𝐂𝐇𝟐 − 𝐂𝐎𝐎𝐇 (D) 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐇𝟐 𝐎𝐇
APNI KAKSHA 25
9. 2-hexyne can be converted into trans-2-hexene by the action of: [IIT-2004]
(A) 𝐇𝟐 − 𝐏𝐝 − 𝐁𝐚𝐒𝐎𝟒 (B) 𝐋𝐢 in liq. 𝐍𝐇𝟑
(C) 𝐇𝟐 − 𝐏𝐭𝐎𝟐 (D) 𝐍𝐚𝐁𝐇𝟒
10. The best reagent to convert pent-3-en-2-ol into pent-3-en-2-one is [AIEEE 2005]
(A) Acidic dichromate (B) Acidic permanganate
(C) Pyridinium chloro-chromate (D) Chromic anhydride in glacial acetic acid
Paragraph for Question No. 11 to 13
In the following reaction sequence, products 𝐈, 𝐉 and 𝐋 are formed. 𝐊 represents a reagent.
11. The structure of the product 𝐈 is [JEE-2008]
(A) (B)
(C) (D)
12. The structures of compounds 𝐉 and 𝐊, respectively, are [JEE-2008]
(A) (B)
(C) (D)
13. The structure of product 𝐋 is [JEE-2008]
(A) (B)
(C) (D)
14. Which of the following will change the colour of acidic dichromate solution.
[JEE Mains-2013]
(A) (B)
(C) (D)
APNI KAKSHA 26
15. [JEE Mains-2013]
(A) (B)
(C) (D)
16. Major product of reaction is? [JEE Mains-2013]
(A) (B) (C) (D)
17. The most suitable reagent for the conversion of 𝐑 − 𝐂𝐇𝟐 − 𝐎𝐇 → 𝐑 − 𝐂𝐇𝐎 is
[JEE Mains 2014]
(A) 𝐂𝐫𝐎𝟑 (B) PCC (Pyridinium chlorochromate)
(C) 𝐊𝐌𝐍𝐎𝟒 (D) 𝐊 𝟐 𝐂𝐫𝟐 𝐎𝟕
18. Consider all possible isomeric ketones including stereoisomers of 𝐌𝐖 = 𝟏𝟎𝟎, All these isomers
are independently reacted with 𝐍𝐚𝐁𝐇𝟒 (NOTE : stereoisomers are also reacted separately) The
total number of ketones that give a racemic product(s) is/are. [JEE-2014]
19. In the reaction [JEE-2014]
𝐋𝐢𝐀𝐥𝐇𝟒 𝐏𝐂𝐥𝟓 𝐀𝐥𝐂𝐊𝐎𝐇
𝐂𝐇𝟑 𝐂𝐎𝐎𝐇 ⟶ 𝐀 ⟶ 𝐁 ⟶ 𝐂. Final Product 𝐂 is.
(A) 𝐇𝟐 / Lindlar Cat. (B) Cat. hydrogenation
(C) 𝐋𝐢𝐀𝐥𝐇𝟒 (D) 𝐋𝐢/𝐍𝐇𝟑
20. The reagent needed for converting is: [JEE-2014]
(A) 𝐇𝟐 / Lindlar Cat. (B) Cat. hydrogenation

(C) 𝐋𝐢𝐀𝐥𝐇𝟒 (D) 𝐋𝐢/𝐍𝐇𝟑
APNI KAKSHA 27
21. Reagent(s) which can be used to bring about the following transformation is(are): [JEE-2016]
(A) 𝐋𝐢𝐀𝐥𝐇𝟒 in (𝐂𝟐 𝐇𝟓 )𝟐 𝐎 (B) 𝐁𝐇𝟑 in 𝐓𝐇𝐅

(C) 𝐍𝐚𝐁𝐇𝟒 in 𝐂𝟐 𝐇𝟓 𝐎𝐇 (D) Raney 𝐍𝐢/𝐇𝟐 in THF
22. The major product obtained in the following reaction is: [JEE MAINS-2017]
(A) (B)
(C) (D)
(𝟏)𝐀𝐥𝐇(𝐢−𝐁𝐮𝟐 )
23. The major product of following reaction is : 𝐑 − 𝐂 ≡ 𝐍 ⟶ [JEE MAIN-2019]
(𝟐)𝐇𝟐 𝐎
(A) 𝐑𝐂𝐇𝐎 (B) 𝐑𝐂𝐎𝐎𝐇 (C) 𝐑𝐂𝐇𝟐 𝐍𝐇𝟐 (D) 𝐑𝐂𝐎𝐍𝐇𝟐

24. The major product ' 𝐗 ' formed in the following reaction is: [JEE MAIN-2019]
(A) (B)
(C) (D)
APNI KAKSHA 28
25. The product of the following reaction is: [JEE MAIN-2019]
(A) (B)
(C) (D)
(A) (B)
(C) (D)
27. The major product obtained in the following reaction is: [JEE MAIN-2019]
(A) (B)
(C) (D)
APNI KAKSHA 29
28. Which of the following compounds reacts with ethylmagnesium bromide and also
decolourizes bromine water solution [JEE MAIN-2019]
(A) (B)
(C) (D)
(A) (B) (C) (D)
(A) (B) (C) (D)
31. The major product(s) obtained in the following reaction is/are: [JEE MAIN-2019]
(A) (B)
(C) (D)
APNI KAKSHA 30
(A) (B)
(C) (D)
𝐋𝐢𝐀𝐥𝐇𝟒
𝐂𝐇𝟑 𝐂𝐇 = 𝐂𝐇𝐂𝐎𝟐 𝐂𝐇𝟑 ⟶
(A) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐇𝐎 (B) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐎𝟐 𝐂𝐇𝟑
(C) 𝐂𝐇𝟑 𝐂𝐇 = 𝐂𝐇𝐂𝐇𝟐 𝐎𝐇 (D) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐂𝐇𝟐 𝐎𝐇
34. Which of the following is NOT a correct method of the preparation of benzylamine from
cyanobenzene? [JEE MAIN-2019]
(A) 𝐇𝟐 /𝐍𝐢 (B) (i) 𝐇𝐂𝐥/𝐇𝟐 𝐎 (ii) 𝐍𝐚𝐁𝐇𝟒
(C) (i) 𝐋𝐢𝐀𝐥𝐇𝟒 (ii) 𝐇𝟑 𝐎 +
(D) (i) 𝐒𝐧𝐂𝐥𝟐 + 𝐇𝐂𝐥 (gas) (ii)𝐍𝐚𝐁𝐇𝟒
(1)NaBH (2)PBr (3)Mg/Ether (4)CO (5)H
35. Hex-3-ynal ⎯⎯⎯⎯
4
→⎯⎯⎯
3
→⎯⎯⎯⎯→⎯⎯⎯
2
→⎯⎯⎯
→ (𝐗), formed product 𝐗 will be:
[JEE MAIN 2020]
(A) (B)
(C) (D)
36. Consider the following reactions [JEE MAIN 2020]

'A' ⎯⎯⎯⎯
Ozonolysis
→ 'B'+ 'C'
(C6H14 )
APNI KAKSHA 31
(A) (B)
(C) (D)
`
37. Reagent used for the given conversion is: [JEE-MAIN 2020]
(A) 𝐇𝟐 , 𝐏𝐝 (B) 𝐁𝟐 𝐇𝟔 (C) 𝐍𝐚𝐁𝐇𝟒 (D) 𝐋𝐢𝐀𝐥𝐇𝟒
38. Three isomers 𝐀, 𝐁 and 𝐂( 𝐦𝐨𝐥. formula 𝐂𝟖 𝐇𝟏𝟏 𝐍) give the following results
[JEE-MAIN 2020]
Diazotization
𝐀 and 𝐂 ⟶
(𝐢𝐢)𝐎𝐱𝐢𝐝𝐚𝐭𝐢𝐨𝐧
(𝐢)𝐇𝐲𝐝𝐫𝐨𝐥𝐲𝐬𝐢𝐬 𝐑(𝐏𝐫𝐨𝐝𝐮𝐜𝐭𝐨𝐟𝐀)
(𝐊𝐌𝐧𝐎𝟒 +𝐇+ )
𝐏 + 𝐐→ +
𝐒(𝐏𝐫𝐨𝐝𝐮𝐜𝐭𝐨𝐟𝐂)
𝐑 has lower boiling point than 𝐒
𝐂𝟔 𝐇𝟓 𝐒𝐎𝟐 𝐂𝐥
𝐁 ⟶ alkali-insoluble product
𝐀, 𝐁 and 𝐂, respectively are
39. The most suitable reagent for the given conversion is: (JEE MAIN 2020)
(A) 𝐇𝟐 , 𝐏𝐝 (B) 𝐁𝟐 𝐇𝟔 (C) 𝐍𝐚𝐁𝐇𝟒 (D) 𝐋𝐢𝐀𝐥𝐇

40. In the reaction given below, the total number of atoms having sp2 hybridization in the major
product P is ______. [JEE Adv -2021]
APNI KAKSHA 32
41 The major products A and B in the following set of reactions are: [JEE-MAINS 2021]
(A) (B)
(C) (D)
42. If the reaction sequence given below is carried out with 15 moles of acetylene, the amount of the
product D formed (in 𝐠 ) is______. [JEE Adv -2022]
The yields of A,B,C and D are given in parentheses.

[Given: Atomic mass of H = 1, C = 12, O = 16, Cl = 35]
43. The number of −𝐂𝐇𝟐 - (methylene) groups in the product formed from the following reaction
sequence is_______. [JEE Adv -2022]
44. The major products obtained from the reactions in List-II are the reactants for the named
reactions mentioned in List-I. Match List-I with List-II and choose the correct option.
[JEE Adv-2023]
List-I List-II
𝐙𝐧−𝐇𝐠,𝐇𝐂𝐥
(P) Etard reaction (1) Acetophenone →
(i) 𝐊𝐌𝐧𝐎𝟒 ,𝐊𝐎𝐇,𝚫
(Q) Gattermann reaction (2) Toluene →
(ii) 𝐒𝐎𝐂𝐥𝟐
𝐂𝐇𝟑 𝐂𝐥
(R) Gattermann-Koch reaction (3) Benzene →
anhyd. 𝐀𝐥𝐂𝐥𝟑
𝐍𝐚𝐍𝐎𝟐 /𝐇𝐂𝐥
(S) Rosenmund reduction (4) Aniline →
273-278 K
𝐙𝐧,𝚫
(5) Phenol ⟶
(A) 𝐏 → 𝟐; 𝐐 → 𝟒; 𝐑 → 𝟏; 𝐒 → 𝟑 (B) 𝐏 → 𝟏; 𝐐 → 𝟑; 𝐑 → 𝟓; 𝐒 → 𝟐
(C) 𝐏 → 𝟑; 𝐐 → 𝟐; 𝐑 → 𝟏; 𝐒 → 𝟒 (D) 𝐏 → 𝟑; 𝐐 → 𝟒; 𝐑 → 𝟓; 𝐒 → 𝟐
APNI KAKSHA 33
ANSWER KEY
EXERCISE # I
1. D 2. A 3. C 4. D 5. C 6. AC 7. A
8. C 9. B 10. AC 11. C 12. C 13. C 14. C
15. C 16. B 17. C 18. D 19. AC 20. D 21. D
22. C 23. C 24. C 25. A 26. B 27. B 28. D
29. A 30. C 31. C 32. B 33. ABCD 34. B 35. BC
36. AC 37. ABCD 38. BD 39. D 40. ABCD 41. C
EXERCISE # II
1. C 2. CD 3. D 4. ACD 5. ABC 6. ABCD 7. C
8. ACD 9. D 10. A 11. ABC 12. C 13. AB
14. (A)→P,R,S; (B)→Q; (C)→R,S; (D)→Q
15. 4 16. 4 17. A 18. B 19. A 20. BC 21. A
22. ABD 23. ABC
24.
25. (a) 𝐏𝐡– 𝐂𝐇𝟐 – 𝐂𝐇𝐎; (b) (C)

26. (i) Cis & trans 2-butene & 1-butene;
(ii)
(iii) Zero (Neo-pentane cannot be prepared by catalytic hydrogenation of alkene);
(iv) One
(v) Including optical = 4 , Excluding optical = 3

27.
APNI KAKSHA 34
28.
1. A 2. 3. D 4. A 5. A 6. B
7. B 8. D 9. B 10. D 11. D 12. A
13. C 14. A 15. C 16. A 17. B 18. 5
19. A 20. D 21. CD 22. C 23. A 24. B
25. A 26. B 27. B 28. C 29. B 30. B
31. A 32. B 33. C 34. B 35. A 36. B
37. B 38. D 39. B 40. 12 41. 0 42. 136
43. 0 44.
APNI KAKSHA 35
SOLUTION
18. M. wt 100 of ketone
So m, formula = 𝐂𝟔 𝐇𝟏𝟐 𝐎
(1 : 2 : 3 : 6 : 7 )
19.
Reduction of 𝐂𝐇𝟑 𝐂𝐎𝐎𝐇 will produce 𝐂𝐇𝟑 – 𝐂𝐇𝟐 – 𝐎𝐇(𝐀) Now reaction of 𝐂𝐇𝟑 – 𝐂𝐇𝟐 – 𝐎𝐇(𝐀)
with 𝐏𝐂𝐥𝟓 will produce 𝐂𝐇𝟑 – 𝐂𝐇𝟐 – 𝐂𝐥(𝐁). Now alcoholic KOH with Et–Cl will produce
𝐂𝐇𝟐 = 𝐂𝐇𝟐 (𝐂) Ethylene by 𝐄𝟐 elemination. Thus Ans. is (𝟏) Ethylene.
APNI KAKSHA 36
35.
36.
37. 𝐁𝟐 𝐇𝟔 is very selective and usually used to reduce acid to alcohol

38.
APNI KAKSHA 37
39. 𝐁𝟐 𝐇𝟔 is very selective and usually used to reduce acid to alcohol.
40.
The total number of atoms having sp2 hybridization in the major product (P) = 12
This includes 4 C-atoms, 4 N-atoms and 4 O-atoms.
APNI KAKSHA 38
41.
42.
43.
APNI KAKSHA 39
(Organic Chemistry) Aldol Similar Name Reaction
HALOGENATION OF THE 𝛂-CARBON OF ALDEHYDES AND KETONES
(I) Acid-Catalyzed halogenation: -
When Br2 , Cl2 and I2 is added to an acidic solution of an aldehyde or a ketone, a halogen
replaces one of the α-hydrogens of the carbonyl compound. Halogenation takes place through
the slow formation of an enol followed by rapid reaction of the enol with the halogen.
Mechanism:
Step - I:
Step - II:
Step - III:
IInd Base-Catalyzed halogenation: - In the presence of excess base and excess halogen, a
methyl ketone is converted first into a trihalo-substituted ketone and then into a carboxylic
acid.
Mechanism:
APNI KAKSHA 1
Q.1 Identify the compounds which can show iodoform reaction and complete the reaction?
Q.2 Complete the following given reaction:
APNI KAKSHA 2
Q.3 Select the compound which does not show haloform reaction is/are:
(A) (B)
(C) Pyruvic acid (D)
Q.4
(𝐙) is:
(A) 𝐏𝐡 − 𝐂𝐇 = 𝐂𝐇 − 𝐂𝐇𝐎 (B)
(C) (D)
Q.5 Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by:
(A) I2 /NaOH (B) NaOH (C) NaCN/HCl (D) 2,4-DNP
Q.6 Which of the reagent is used to convert 2-Butanone into propanoic acid –
(A) NaOH, I2 /H + (B) Tollen's reagent (C) Fehling solution (D) NaOH, NaI/H +
Paragraph for Q.07 to Q.09
Q.7 Which one of the following reagent is best suitable for distinction between 𝑃1 and P2 –
(A) Braddy's reagent (2,4 DNP) (B) NaHSO3
(C) NaHCO3 (D) NaOH/I2
Q.8 Select the correct statement among the following -
(A) P1 will show aldol reaction & P2 will show cannizaro reaction
(B) P1 will show cannizaro reaction & P2 will show aldol reaction
(C) Both P1 &P2 will show cannizaro reaction
(D) Both P1 &P2 will show aldol reaction
APNI KAKSHA 3
Q.9 P2 ⎯⎯⎯⎯ ⎯
(i)conc.NaOH
( ii) H+
→ products
Select incorrect statement for the above reaction -

(A) It is a redox reaction
(B) It is a disproportion reaction
(C) Two products formed are alcohol & carboxylic acid
(D) It is an intramolecular reaction
Q.10 Which of the following will give yellow precipitate with NaOH/I2
(A) (B) CI3 CHO (C) (D) EtOH
Q.11
CaOCl2
W ⎯⎯⎯ →CHCl3 + Y
CaOCl2
X ⎯⎯⎯ →CHCl3 + Y
Y + Z ⎯⎯⎯⎯ Dry
Distillation
→Organicproduct ( s ) + CaCO3
Which of the following is major organic product
(A) CH3 − CHO (B) CH3 − CO − CH3
(C) CH3 − CH = CH − CH3 (D) HCHO
Q.12 Correct option regarding following reaction sequence.
(A) T is homologue of ' X ' (B) R is sodium salt of
(C) P can produce 𝐒 with NaOI (D) R is sodium salt of
Q.13 Which of the following compounds(s) give a sweet-smelling product having anesthetic use in
presence of Cl2 , NaOH, Δ.
(A) (B)
(C) (D)
APNI KAKSHA 4
Q.14 Reaction in which product can show positive haloform test :-
(A) CH3MgBr + PhCN ⎯⎯⎯
H O
→ (B) CH3 − CH2MgBr + Ph − COOEt ⎯⎯⎯
H O
→
3 3
(1 : 1)
(C) CH3MgBr + H − C − OMe ⎯⎯⎯ →

NH4Cl
(D) CH MgBr + H − C − OMe ⎯⎯⎯ →
(1:1) ||
3 NH4Cl
||
O O
Q.15 In which reaction haloform is obtained as one product: -

(A) Electrolysis of ethanolic aqueous solution of NaCl
(B) Isopropanol with bleaching powder
(C) Chlorination of methane in sun light
(D) Chloral is treated with NaOH
(2) ALDOL CONDENSATION
The 𝛂 − hydrogen of carbonyl compounds are acidic due to the fact that the anion (enolate ion)
is stabilized by resonance.
Base catalysed Aldol

In aqueous base, two acetaldehyde molecules react to form β-hydroxy aldehyde called aldol.
The reaction is called Aldol condensation. The enolate ion is the intermediate in the aldol
condensation of aldehyde and ketone. Acetaldehyde for instance, forms a dimeric product aldol
in presence of a dilute base (≈ 10%NaOH)
Mechanism:
APNI KAKSHA 5
Aldols are stable and may be isolated. They, however can be dehydrated easily by heating the
basic reaction mixture or by a separate acid catalyzed reaction. Thus if the above reaction is
heated the product is dehydrated to 2-butenal (crotonaldehyde).
Acid cataysed Aldol:
In acid catalysed aldol condensation enol form of carbonyl is the nucelophile in place of
enolate.
Mechanism:
Q.1 Write the product and mechanism for given reactions.
Q.2 Identify the intramolecular aldol product?
APNI KAKSHA 6
Q.3 Find out the total number of possible aldol products (including and excluding stereo products).
(I) C6H5 − CHO + CH3 − CHO ⎯⎯⎯⎯
NaOH/HOH
5ºC
→
(II) CH3 − CH = O + CH3 − CH2 − C − CH3 ⎯⎯⎯⎯

NaOH/HOH
5ºC
→
||
O
Q.4 Identify the structure of substrate?
Q.5 Complete reaction sequence:
Q.6 Complete the following reactions:
Q.7
(A) (B)
(C) (D)
APNI KAKSHA 7
Q.8 Consider following intramolecular aldol condensation reaction:
(A) (B)
(C) (D)
Q.9 Product 'E' is:
(A) (B)
(C) (D)
Q.10 Product '𝐘' formed in the given reaction is:
(A) (B) (C) (D)
Q.11 Product 'D' is:
(A) CH3 − CH2 − CH = CH2 (B) CH3 − CH2 − CH2 − CHO

(C) CH2 − CH2 − CH2 − COOH (D) CH2 = CH − CH = CH2
APNI KAKSHA 8
−

Q.12 CH3CH = CHCHO ⎯⎯→⎯⎯
OH
aldol
→ A, A is
(A) 𝐶𝐻3 (𝐶𝐻 = 𝐶𝐻)3 𝐶𝐻𝑂 (B) CH3 CH2 CH2 (CH = CH)2 CHO
(C) CH3 (CH2 CH2 )3 CH = CH − CHO (D) None is correct
Q.13 Which one of the following will undergo aldol reaction most readily.
(A) (B) (C) (D)
NaOH,  NaOH, 
Q.14 MeCHO ⎯⎯⎯ → A ⎯⎯⎯ → B; B is:
(A) Me(CH = CH)3 CHO (B) MeCH = CHCHO
(C) Me(CH = CH)2 − CHO (D) Me + (CH = CH)4 CHO
(3) CLAISEN CONDENSATION
Esters undergo SN AE Reaction. when attacked by a Nu− generated by the interaction of a base
(usually base related to the Alkoxy anion of ester) with one of the molecule of ester and this
Nu− attacks on another molecule. The reaction over all is considered as condensation of ester
known as claisen ester condensation.
Mechanism:
Sometimes, when two ester group are present within the molecule then the condensation
occurs intramolecule then cyclization caused thus is known as Dieckmann cyclization or
Dieckmann's condensation.
APNI KAKSHA 9
()i EtOK
Q.1 MeCOOEt ⎯⎯⎯⎯⎯
( ii ) Acidification→ A
()i MeOK
Q.2 EtCOOMe ⎯⎯⎯⎯⎯
( ii ) Acidification→ B
() i MeOK
Q.3 MeCOOMe + EtCOOMe ⎯⎯⎯⎯⎯
( ii ) Acidification→C
() 2 5 i C H ONa
Q.4 C6H5COOC2H5 + CH3COOC2H5 ⎯⎯⎯⎯⎯
( ii) Acidification→D + D'
Q.5
Q.6
Q.7
(4) PERKIN CONDENSATION

In Perkin reaction, condensation has been effected between aromatic aldehydes and aliphatic
acid anhydrides in the presence of sodium or potassium salt of corresponding acid of that
anhydride, to yield α, β - unsaturated aromatic acids.
APNI KAKSHA 10
Q.1
Q.2
Q.3
Q.4
(5) KNOEVENAGEL REACTION

Reaction of active methylene group with aldehyde & Ketones is known as knoevenagel
reaction.
High reactivity of the methylene group of the active methylene compound prevents self-
condensation of the aldehyde.
APNI KAKSHA 11
Q.1
Q.2
Q.3
Q.4
Q.5
Q.6
Q.7
Q.8
(6) MICHAEL ADDITION

Michael Addition: α − β unsaturated carbonyl compound undergo michael reaction with
compounds having active methylene. Many different nuclephile can add to α − β
unsaturated carbonyl compound. When the nucleophile is an enolate the addition reaction has
a special name MICHAEL REACTON.
APNI KAKSHA 12
Mechanism:
Q.1
Q.2
Q.3
Q.4
Q.5
(7) REFORMATSKY REACTION

α-halo esters when treated with Zn in gives organometallic halo ester which provides the
attacking Nu− for the another reactant, which is a carbonyl compound. When Nu− attacks on
carbonyl compound it gives an intermediate which upon acidic hydrolysis followed by heating,
results in formation of α, β - unsaturated acid. The overall reaction is known as Reformatsky
reaction.
APNI KAKSHA 13
Q.1 C6H5COCH3 + BrCH2COOEt ⎯⎯⎯1.Zn

⎯
2.H O ,
→A
3
Q.2
Q.3
Q.4
Q.5
Q.6
APNI KAKSHA 14
Q.7
Q.8 Matrix Match:

Match the column-
Column – I Column – II
(A) (P) Perkin's reaction.
(B) (Q) Reformatskii reaction.
( ) 31 CH COONa/ 
(C) Ph − CHO + CH3COOCOCH3 ⎯⎯⎯⎯⎯
(2) H O / 
→ (R) Product is a carboxylic acid with
3
aromatic ring within the same

molecule.
(D) (S) Double bond equivalent of the
product formed is less than or equal to

8.
(T) The major product cannot show
optical isomerism
(8) CANNIZARO REACTION
This reaction is given by aldehyde having no α - hydrogen in the presence of conc. NaOH/Δ or
KOH/Δ.
Mechanism:
In the presence of a very strong concentration of alkali, aldehyde first forms a doubly charged
anion (I) from which a hydride anion is transferred to the second milecule of the aldehyde to
form acid and an alkoxide ion. Subsequently, the alkoxide ion acquires a proton from the
solvent.
APNI KAKSHA 15
Q.1 Which of following will not undergo Cannizaro reaction
(A) (B)
(C) (D) Cl3 C − CHO
Q.2
Product (C) & (D) are:

(A) Ph − CO2 H, Ph − OH (B) Ph − CO−
2 , HCO2
−
(C) Ph − CH2 OH, H − CO2− (D) Ph − CO−

2 , CH3 OH
Q.3
(A) H2 C = CH − CO2 H (B)
(C) (D) H2 C = C = O
APNI KAKSHA 16
Q.4 (i) HCHO ⎯⎯⎯
NaOD

→ (ii) DCHO ⎯⎯⎯
NaOD

→
 18 
Q.5 (i) Ph − CHO ⎯⎯⎯→
OD/DOD

(ii) Ph − CHO ⎯⎯⎯
OH

→
Q.6 (i) Ph − CHO + HCHO ⎯⎯

KOH

→ (ii)
Q.7 (i) MeCH2 − CHO ⎯⎯

KOH

→ (ii) Me2CH − CHO ⎯⎯⎯⎯
conc.KOH

→
Q.8 (i) Me − NO2 + HCHO ⎯⎯→
KOH
(ii) MeCHO − HCHO ⎯⎯→
KOH
( excess ) ( excess )
+
Q.9 PhCOCHBr2 ⎯⎯⎯
Aq.OH
→ A ⎯⎯⎯
Conc.OH
→ B ⎯⎯
H
→ ;the compound ' 𝐂 ' is:
(A) PhCH(OH)CHO (B) PhCH(OH)COOH
(C) PhCOOH (D) None of these
Q.10 Matrix Match:
Match the column-
Column – I Column – II
(A) HCHO + NaOD (conc.) (P) DCOO− + CDH2 OH
(B) DCHO + NaOH (conc.) (Q) DCOO− + CD2 OH
(C) DCDO + NaOH (conc.) (R) DCOO− + CDH2 OD
(D) DCHO + NaOD (conc.) (S) HCOO− + CH3 OD
Q.11
(A) (B) (C) (D)
Q.12
(A) (B) (C) (D)
Q.13 The Cannizaro reaction of PhCOCHO forms the product(s)

(A) PhCOCH2 OH + PhCOCO2− (B)
(C) PhCO2− + PhCOCH2 OH (D) Both (A) and (C)
APNI KAKSHA 17
Q.14 Product is:
(A) (B)
(C) (D)
Q.15
True about this reaction is / are

(A) Cannizaro name is associated with this reaction
(B) It is a disproportion reaction
(C) It is a bimolecular reaction in r.d.s.
(D) All of these
Q.16
End product (B) of above reaction is:
(A) (B) (C) (D)
Q.17 The major product pair of the following reaction will be:
(A) (B)
(C) (D)
APNI KAKSHA 18
Q.18 Reactant 'X' will be:
(A) (B)
(C) (D)
(9) BENZIL-BENZILIC REARRANGEMENT OR BENZILIC ACID REARRANGEMENT

The base catalysed reaction of 1,2-diketones to a salt of -2-hydroxy carboxylic acid is known as
Benzilic acid rearrangement, this reaction is mainly applicable when aryl group is present on
both carbonyl carbons.
Mechanism:
Q.1
Q.2
APNI KAKSHA 19
Q.3
Q.4
Q.5
Q.6 Ph − CHO ⎯⎯
KCN

→P1 ⎯⎯⎯
Fenton's
Reagent
→P2 ⎯⎯⎯
NaOH
(2)H+
→P3
(10) TISCHENKO REACTION /CONDENSATION

(1) This reaction takes place between two molecules of aldehydes.
(2) Reaction is catalysed by aluminimum ethoxide.
(3) This is a two-step reaction, i.e., redox reaction followed by ester formation. Thus, this
reaction is extension of Cannizzaro reaction.
Mechanism:
(C H O) Al
Q.1 CH3 − CHO ⎯⎯⎯⎯
2 5 3

→?
(C H O) Al
Q.2 CH3 − CH2 − CHO ⎯⎯⎯⎯
2 5 3

→?
(C H O) Al
Q.3 OHC − CH2 − CH2 − CH2 − CHO ⎯⎯⎯⎯
2 5 3

→?
( C H O) Al
Q.4 CH3CHO + CH3 − CH2 − CHO ⎯⎯⎯⎯
2 5 3

→?
(11) COREY HOUSE SYNTHESIS
Reaction of Gilman's reagent with alkyl halide gives alkane as one of the product which is
known as Corey House synthesis,
APNI KAKSHA 20
To obtained good yield of alkane, the alkyl halide R′ − X must be either a methyl halide, a
primary alkyl halide, or a secondary cycloalkyl halide. (Best CH3 X, if possible) Preparation of
Gilman reagent:
→R2Cu LI
Cu − X,  
R − X ⎯⎯→
2Li
− LiX
RLi ⎯⎯⎯ − LiX
(2mole) Gilmanreagent
(alkylLithium)
Complete the following reaction sequence:
Q.1 CH3 − I ⎯⎯Li

Et2O
→( A ) ⎯⎯
Cul

→(B) ⎯⎯⎯⎯⎯⎯ 
→(C)
CH3CH2CH2CH2CH2I
CH3CH2CH2CH2Br ⎯⎯Li
Et2O
→(D) ⎯⎯
Cul

→(E) ⎯⎯⎯⎯⎯⎯
CH3CH2CH2CH2CH2Br

→(F )
Q.2 ( A ) ⎯⎯
Cl
2
h
→ ( B) ; ( B) ⎯⎯→(C)
Li
CH3Cl
(C) ⎯⎯ → ( D)
CuCl

; ( D) CH3 − CH − CH2 − CH3
 |
CH3
( ii ) CuBr,→ ( A ) ⎯⎯⎯ → ( B)
() i Li CH3 −Cl
Q.3 CH3 − CH2 − Br ⎯⎯⎯⎯ 
Q.4
Q.5
Q.6 How can you prepare following compounds using corey house synthesis.
(i) (ii) CH2 = CH − CH2 − CH3 (iii)

14
Q.7 (CH3 )2 CuLi + CH2 = CH − C H2 − Cl →
Q.8
Q.9
Q.10
APNI KAKSHA 21
Q.11 Which of the combination of Gilman's reagent & alkylhalide will be most suitable for
preparation of following compounds.
(i) CH3 − CH2 − CH3 (ii) (iii)
(iv) (v)
Q.12 Identify the product of following reactions:
(a) (b)
(12) BENZOIN CONDENSATION

The Benzoin Condensation is a coupling reaction between two aldehyades that allows the
preparation of 𝜶-hydroxyketones.
Mechanism of Benzoin Condensation
A strong base is now able to deprotonate at the former carbonyl C-atom.
A second equivalent of aldehyde reacts with this carbanion, elimination of the catalyst
regenerates the carbonyl compound at the end of the reaction
APNI KAKSHA 22
ANSWER KEY
(1) HALOGENATION OF THE 𝜶-CARBON OF ALDEHYDES AND KETONES
Q.1 (1,2,5,7,9,11)
Q.2 (i) (ii) CH3 − COO− + CHI3
(iii) (iv)
Q.3 (A, B)
Q.4 (C)
X: PhCH2 CH2 OH Y: PhCH2 CHO
Q.5 (A) Q.6 (A)
Q.7 (B)
(A) Both ketone & aldehyde react with braddy's reagent
2, 4 dinitrophenyl hydrazine.
(B) With NaHSO3 only aldehyde give crystalline bisulphite adduct whereas hindered ketone is
unable react.
(C) NaHCO3 will not react any of them.
(D) Both P1 &P2 are unable to form idoform with NaOH/I2
Q.8 (A)
For aldol 𝛼H should be present i.e. 𝑃1 where as 𝑃2
Will give cannizaro's as there is no. 𝛼H in P2.

Q.9 (D)
The above reaction is intermolecular redox reaction. In which desprotionation is taking place
as a result of which 2 different products are formed from singlet reactant.
APNI KAKSHA 23
Q.10 (A,B,C,D)
Q.11
Q.12 (A, B, C)
Q.13 (A, B, D)
Q.14 (A, B, C, D)
Q.15 (A, B, C, D)
(2) ALDOL CONDENSATION
Q.1
APNI KAKSHA 24
Q.2
Q.3
Q.4
Q.5
Q.6
APNI KAKSHA 25
Q.7 (C)
Intramolecular aldol condensation the 1,4-additon and finally clemmesion reduction.
Q.8 (D)
Q.9 (D)
Q.10 (B)
Ozonolysis followed by intramolecular aldol.
Q.11 (C)
Q.12 (A)
Q.13 (A)
Q.14 (A)
(3) CLAISEN CONDENSATION
Q.1
Q.2
APNI KAKSHA 26
Q.3 4 products
Q.4
Q.5
Q.6
(4) PERKIN CONDENSATION
Q.1
Q.2
Q.3
Q.4 CH3 COOCOCH3

(5) KNOEVENAGEL REACTION
Q.1 Q.2
Q.3 HOOC − CH = CH − COOH Q.4
Q.5 Ph − CH = CH − NO2 Q.6
APNI KAKSHA 27
Q.7
Q.8
(6) MICHAEL ADDITION
Q.1 Q.2
Q.3 Q.4
Q.5
(7) REFORMATSKY REACTION
Q.1 Q.2
Q.3 Q.4
APNI KAKSHA 28
Q.5 Q.6
Q.7
Q.8 (A)-RST, (B) -Q,R,S,T (C)-P,R,S,T (D) R,T
(8) CANNIZARO REACTION

Q.1 (D) As Cl3 C − CHO given chloroform
Q.2 (C) In cross cannizzaro reaction move reactive carbonyl compound is oxidised & less in
reduced.
Q.3 (B) Intramolecular cannizzaro followed by heating effect
Q.4 (i) CH3 OD + HCOONa (ii) DCH2 OD + DCOONa
Q.5 (i) PhCH2 OD + PhCOONa (ii) Ph − CH2 OH + PhCOONa
Q.6 (i) Ph − CH2 OH + HCOOK (ii)
Q.7 (i) (ii) Me2 CH − CH2 OH + Me2 CHCOOK
Q.8 (i) (ii)
Q.9 (B)
Q.10 (A) → S; (B) → P; (C) → Q; (D) → R

Q.11 (A)
APNI KAKSHA 29
Q.12 (D)
Q.13 (B)
Q.14 (C)
Q.15 (A)
option A is correct.
Q.16 (B)
Q.17 (B) Cross cannizaro reaction

Q.18 (A)
(9) BENZIL-BENZILIC REARRANGEMENT OR BENZILIC ACID REARRANGEMENT
Q.1 Q.2
Q.3
APNI KAKSHA 30
Q.4 Q.5
Q.6
(10) TISCHENKO REACTION/CONDENSATION
Q.1 Q.2
Q.3 Q.4 4 products
(11) COREY HOUSE SYNTHESIS

Q.1 (A) CH3 Li, (B) (CH3 )2 CuLi,
(C) CH3 − CH2 CH2 CH2 CH2 CH3 , (D) CH3 CH2 CH2 CH2 Li,
(E) (CH3 CH2 CH2 CH2 )2 CuLi, (F) CH3 CH2 CH2 CH2 − CH2 CH2 CH2 CH2 CH3
Q.2
Q.3 (A) [CH3 CH2 ]⊖

2 CuLi
⊕
(B) CH3 − CH2 − CH3
Q.4
Q.5
APNI KAKSHA 31
Q.6
14
Q.7 CH3 − CH2 − CH = CH2
Q.8 not available
Q.9
Q.10
Q.11
Q.12
APNI KAKSHA 32
(Organic Chemistry) AROMATIC COMPOUNDS
EXERCISE # I
Q.1 Which of the following is not an aromatic compound:
(A) (B) (C) (D)
Q.2 Which of the following group is divalent:

(A) Benzoyl (B) Benzyl (C) Benzal (D) p-Tolyl
Q.3 Benzene is a resonance hybrid mainly of two Kekule structures. Hence:
(A) Half of the molecules correspond to one structure, and half of the second structure
(B) At low temperatures benzene can be separated into two structures
(C) Two structures make equal contribution to resonance hybrid
(D) An individual benzene molecule changes back and forth between two structures
Q.4 How many 𝜋 electron are there in the following species:
(A) 2 (B) 4 (C) 6 (D) 8

Q.5 The number of benzylic hydrogen atoms in ethylbenzene is:
(A) 3 (B) 5 (C) 2 (D) 7
Q.6 Which one of the following is the most basic compound in water :
(A) C6 H5 − NH2 (B) C6 H5 − NHCH3 (C) C6 H5 − N(CH3 )2 (D) C6 H5 N(C2 H5 )2
Q.7
(A) (B)
(C) (D) None is correct
Q.8 In the sulphonation, acetylation and formylation of benzene the group of effective electrophiles
would be :
+ + + +
(A) SO+
3 , CH3 C ≡ O, HO (B) SO3 , CH3 − C ≡ O, HO
(C) SO3 , CH3 CHO, CO + HCl (D) HSO3 , CH3 CO, HCO
APNI KAKSHA 69
Q.9 o/p ratio in highest for nitration of which of the following compound?
(A) Ethyl benzene (B) Toluene (C) Isopropyl benzene (D) Tertiarybutyl benzene
Q.10 Which can be used to generate NO+
2 in nitration of benzene ring
(A) HNO3 + H2 SO4 (B) HNO3 + HClO4 (C) N2 O5 (D) All

Q.11 Product obtained when benzoyl acetic acid is heated with soda-lime is:
(A) (B) (C) (D)
Q.12 For the electrophilic substitution reaction involving nitration, which of the following sequence
regarding the rate of reaction is true?
(A) k C6H6 > k C6D6 > k C6 T6 (B) k C6H6 < k C6 D6 < k C6 T6
(C) k C6H6 = k C6 D6 = k C6 T6 (D) k C6H6 > k C6 D6 < k C6 T6
Q.13 For the electrophilic substitution reaction involving sulphonation, which of the following sequence
regarding the rate of reaction is true?
(A) k C6H6 > k C6D6 > k C6 T6 (B) k C6H6 < k C6 D6 < k C6 T6
(C) k C6H6 = k C6 D6 = k C6 T6 (D) k C6H6 > k C6 D6 < k C6 T6
CH3COCl Zn−Hg
Q.14 C6H6 ⎯⎯⎯
AlCl3
→ A ⎯⎯⎯
HCl
→B
The end product in the above sequence is:

(A) Toluene (B) Ethyl benzene (C) Both the above (D) None
Q.15 p-Nitrotoluene on further nitration gives:
(A) (B) (C) (D)
Q.16 Reaction of SO3 is easier in:

(A) Benzene (B) Toluene (C) Nitrobenzene (D) chlorobenzene
Q.17 Which order is correct for the decreasing reactivity to ring monobromination of the following
compounds:
(I) C6 H5 CH3 (II) C6 H5 COOH (III) C6 H6 (IV) C6 H5 NO2
(A) I > II > III > IV (B) I > III > II > IV (C) II > III > IV > I (D) III > I > II > IV
Q.18 The highest yield of m-product is possible by the electrophilic substitution of the following:
(A) C6 H5 CH3 (B) C6 H5 CH2 COOC2 H5
(C) C6 H5 CH(COOC2 H5 )2 (D) C6 H5 C(COOC2 H5 )3
APNI KAKSHA 70
Q.19 Which of the following will undergo sulphonation at fastest rate?
(A) (B) (C) (D)
Q.20 Aniline under acidic medium, when chlorinated, produces:

(A) o-Chloro aniline (B) m-Chloro aniline
(C) p-Chloro aniline (D) Mixture of ortho and para-chloro aniline
Q.21 When sulphonilic acid (p − H2 NC6 H4 SO3 H) is treated with excess of bromine water, the product is:
(A) Tribromo product (B) Dibromo product
(C) Monobromo product (D) Tetrebromo product
Q.22 In a reaction of C6 H5 Y, the major product (> 60%) is m-isomer, so the group Y is:
(A) −COOH (B) −Cl (C) −OH (D) −NH2
Q.23 An aromatic compound of molecular formula C6 H4 Br2 was nitrated then three isomers of formula
C6 H3 Br2 NO2 were obtained. The original compound is:
(A) o-Dibromobenzene (B) m-Dibromobenzene
(C) p-Dibromobenzene (D) Both A & C
Q.24 Which of the following substituted benzene derivatives would furnish only three isomers in
significant amount when one more substituent is introduced:
(A) (B) (C) (D)
Q.25 Which of the following is most reactive towards sulphonation?

(A) m-Xylene (B) o-Xylene (C) Toluene (D) p-Xylene
Q.26 Ring nitration of dimethyl benzene results in the formation of only one nitro dimethyl benzene.
The dimethyl benzene is:
(A) (B) (C) (D) None of these
APNI KAKSHA 71
Q.27 If meta-nitroaniline is chlorinated, the major product is:
(A) (B)
(C) (D)
Q.28 If p-methoxy toluene is nitrated, the major product is:
(A) (B) (C) (D) No reaction
CrO2 H2O
Q.29 C6H5CH3 ⎯⎯→ A ⎯⎯ →B
The functional group present in B and name of the reaction would be
(A) - CHO, Gattermann aldehyde synthesis
(B) - CHO, Etard reaction
(C) −COCH3 , Friedel Crafts reaction
(D) -CHO, Oxo reaction
Q.30 Etard reaction in the following is:
(A) Oxidation of toluene to benzaldehyde by chromylchloride
(B) Oxidation of toluene to benzaldehyde by alkaline KMnO4
(C) Dry distillation of calcium benzoate
(D) Reaction of benzene with Cl2 in the presence of UV light
Q.31
Compound A and B respectively are:

(A) o-Bromostyrene, benzoic acid (B) p-Bromostyrene, benzaldehyde
(C) m-Bromostyrene, benzaldehyde (D) Styrene dibromide, benzoic acid
APNI KAKSHA 72
Q.32 If the mixture of the following four aromatic compounds on oxidation by strong oxidising agent
gives:
(A) Mixture of C6 H5 CH2 OH + C6 H5 COOH (B) Mixture of C6 H5 CHO + C6 H5 COOH

(C) Only C6 H5 COOH (D) None of the above
Q.33 Methyl group attached to benzene can be oxidised to carboxyl group by reacting with:
(A) Fe2 O3 (B) AgNO3 (C) KMnO4 (D) CrO3
Q.34 Which of the following is/are produced when a mixture of benzene vapour and oxygen is passed
over V2 O5 catalyst at 775 K ?
(A) Oxalic acid (B) Glyoxal (C) Fumaric acid (D) Maleic anhydride
Q.35 Benzene on reaction with 'A' forms which on reaction with 'B' forms
'A' and 'B' are:
(A) Zn(Hg) + conc. HCl, (B)
(C) (D)
Q.36 Which chloroderivative of benzene among the following would undergo-hydrolysis most readily
with aq. NaOH to furnish the corresponding hydroxy derivative.
(A) (B) (C) (D)
Q.37 Major product of this reaction will be :
(A) o-Xylene (B) p-Xylene (C) Both (D) m-Xylene
APNI KAKSHA 73
Q.38 For preparing monoalkyl benzene, acylation process is preferred than direct alkylation because
(A) In alkylation, a poisonous gas is evolved
(B) In alkylation, large amount of heat is evolved
(C) In alkylation, polyalkylated product is formed
(D) Alkylation is very costly
Q.39 Phenol and ethanol are distinguished by the reaction with
(A) Red litmus (B) NaHCO3 (C) FeCl3 (D) Na
Q.40 An aromatic compound ' A C7 H6 Cl2 , gives AgCl on bonding with alcoholic AgNO3 solution, and
′
yields C7 H7 OCl on treatment with sodium hydroxide. 'A' on oxidation gives a mono chlorobenzoic
acid which affords only one mononitro derivative. The compound A is:
(A) (B) (C) (D)
Q.41 (A). Which of the following can be isolated as the product of this
(A) (B) (C) (D)
Q.42 Chloral + product. The product is:
(A) Lindane (B) DDT (C) Teflon (D) Ethaneperchlorate

Indicator (D) ; C & D are
+
HCO3H H3O
Q.43 Acetophenone ⎯⎯⎯ →A ⎯⎯ ⎯→B + C ⎯⎯⎯⎯⎯→
PthalicAnhydride
H+
(A) (B)
(C) (D)
APNI KAKSHA 74
Q.44 Select the reaction giving correct major product:
(A) (B)
(C) (D)
()i NaHCO +
H /H2O Al2O3
Q.45 Phenol ⎯⎯⎯⎯
( ii ) Me−I → A ⎯⎯⎯→ B ⎯⎯⎯⎯
3
CH3COOH,
→C
In this reaction, the end product C is:

(A) Salicylaldehyde (B) Salicylic acid (C) Phenyl acetate (D) Aspirin
Q.46 Major Product is:
(A) (B)
(C) (D)
Q.47
(A) (B) (C) (D) No reaction
Q.48 m-Aminophenol on treatment with NaOH and CO2 gives which of the following as major product?
(A) (B) (C) (D)
APNI KAKSHA 75
Q.49 Stability order of following singlet halocarbene is
(A) CF2 > CCl2 > CBr2 > CI2 (B) CI2 > CBr2 > CCl2 > CF2
(C) CCl2 > CF2 > CBr2 > CI2 (D) CF2 > CI2 > CCl2 > CBr2
CHCl3 /KOH
Q.50 Trans-Butene- 2 ⎯⎯⎯⎯
Solvent
→ Product
(A) (B) (C) (D) Both (A) & (B)
Q.51
(A) (B) (C) (D)
APNI KAKSHA 76
EXERCISE # II
Q.1 In which of the following reaction t-butylbenzene is formed:
BF3 .HF
(A) Benzene + iso-butyl chloride, AlCl3 (B) Benzene +(CH3 )2 C = CH2 ⎯⎯⎯ →
H2SO4 AlCl3
(C) Benzene + t-butyl alcohol ⎯⎯⎯2
→ (D) Benzene +(CH3 )2 C = CH2 ⎯⎯ ⎯→
Q.2 The replacement of a hydrogen atom in benzene by alkyl group can be brought about with the
following reagents :
(A) Alkyl chloride and AlCl3 (B) Alkene and AlCl3
(C) Alkanol and alkali (D) Alkanol and acid
Q.3 Benzene reacts with n-propyl chloride in the presence of anhydrous AlCl3 to give predominantly:
(A) n-Propylbenzene (B) Isopropylbenzene
(C) 3-Propyl-1-chlorobenzene (D) Cumene
Q.4 The structure of the compound that gives a tribromo derivative on treatment with bromine water
is:
(A) (B) (C) (D)
Q.5 Electrophilic attack of NO⊕

2 at meta position is observed in:
(A) (B) (C) (D)
Q.6 Which of the following will undergo nitration faster than benzene?
(A) (B) (C) (D)
Q.7 The good method for converting benzene into n-propyl benzene is:
(A) C6 H6 + CH3 CH2 CH2 Cl + Anhyd. AlCl3
(B) C6 H6 + CH3 CH2 COCl + Anhyd. AlCl3 and then treatment with Zn/Hg/HCl
(C) C6 H6 + CH3 CH2 COCl + Anhyd. AlCl3 and then treatment with H2 Ni
(D) C6 H6 + Anhyd. AlCl3 + cyclopropane
APNI KAKSHA 77
Q.8 Which of the following can be used as reagent in Friedel Crafts reaction?
(A) (B) CH2 = CH − Cl (C) CH3 CH2 Cl (D) CH2 = CH − CH2 − Cl
Q.9 Of the species PhSR, the meta-substituted product is obtained from
(A) PhSR (B) (C) (D)
Q.10 Amongst the following, the moderately activating group is
(A) −NHR (B) −NHCOCH3 (C) (D)−CH3

Q.11 False statement is / are :
(A) Although benzene contains three double bonds, normally it does not undergo addition reaction.
(B) m-Chlorobromobenzene is an isomer of m-bromochlorobenzene.
(C) In benzene, carbon uses all the three p orbitals for hybridization.
(D) An electron donating substitutent in benzene orients the incoming electrophilic group to the
meta position.
Q.12 Benzoic acid may be prepared by the oxidation of:
(A) (B) (C) (D)
Q.13 Identify reactions give ketone product?
(A) (B)
H3 O +
(C) PhMgBr + Me − C ≡ N ⟶ (D)
APNI KAKSHA 78
Q.14 Which of the following reaction(s) will give aromatic product?
(A) (B)
(C) (D)
Q.15 Which of the following statements is/are not true?

(A) All ortho-para directing groups activates the ring towards electrophilic substitution.
(B) Halobenzene is ortho para directing but deactivating in nature
(C) All meta-directing groups have π-bond on the atom directly attached to the ring
(D) All meta directing groups are deactivating.
Q.16 Which of the following is not an ortho-para directing group?
(A) CF3 (B) CCl3 (C) −CH = CH − COOH (D) −N ≐ C
Q.17 Which of the following does not gives Fridel-Crafts reaction?
(A) (B) (C) (D)
Q.18 Which of the following reactions of benzene proves the presence of three carbon-carbon double
bonds in it :
(A) Formation of a triozonide
(B) Hydrogenation of benzene to cyclohexane
(C) Formation of C6 H6 Cl6 by addition of chlorine
(D) Formation of nitrobenzene on heating benzene with a mixture of concentrated nitric acid and
sulphuric acid
Q.19 Which of the following are classified as aromatic ?
(A) 1,2,3-Triphenylcyclopropenium cation (B) Cyclooctatetraenyl dianion
(C) Azulene (D) Annulene [10]
Q.20 Which of the following is/are name of 1,2,3,4,5,6 - hexachloro cyclohexane :
(A) Lindane (B) Gammexane (C) 666 (D) BHC
APNI KAKSHA 79
Q.21 Among the following reaction sequences identify incorrect step :
(A) I-a ; II - b ; III −c; IV −d (B) I-b; II - a ; III −d; IV −d

(C) I-a; II - a ; III - b ; IV – d (D) I-b ; II - a ; III - d ; IV – c
Q.22 How many of following compounds are less reactive than benzene for sulphonation by conc.
H2 SO4 :
(A) 2 (B) 4 (C) 6 (D) 8

Q.23 Decide the correct order of reactivity of following compounds towards halogenation with
(Cl2 + AlCl3 ).
(A) I > II > III > IV (B) II > III > IV > I (C) III > II > IV > I (D) II > III > I > IV
APNI KAKSHA 80
Q.24 Which of the following method(s) is/are not used to prepare p-bromo aniline as major product :
(A) (B)
(C) (D)
Q.25 X is/are -
(A) CHCl3 (B) CCl4 (C) CO2 (D) HCOOH

Q.26 Which product is/are not obtained in following reaction.
(A) (B) (C) (D)
Q.27 E is:
APNI KAKSHA 81
(A) (B) (C) (D)
Q.28
Identify correct statement:

(A) Product C is phenophthalein indicater
(B) Product B gives CO2 effervescence with NaHCO3
(C) Product A formation involves carbocation intermediate
(D) Product B gives no colour with neutral FeCl3
Paragraph for Q.29 to Q.30

Identify reagent used and intermediate products in following conversion.
APNI KAKSHA 82
Q.29 Identify II product –
(A) (B) (C) (D)
Q.30 (III) major product is?
(A) (B)
(C) (D)
Q.31 Match the following:

Column-I (Properties) Column-II (Compound)
(A) CO2 ↑ is evolved from NaHCO3 (P)
(B) Gives libermann nitroso test (Q)
(C) Gives yellow oily liquid with NaNO2 + HCl (R)
(D) Evolve a colourless gas with active metals (S)
APNI KAKSHA 83
Column-I Column-II
(Compound) (Properties)
(A) (P) Group attached with phenyl ring is +M.
(B) (Q) Rate of electrophilic aromatic substitution is less than benzene ring
(C) (R) Group attached with phenyl ring will show (+H) (Hyperconjugation)
(S) Group attached with phenyl ring will show (-H) effect (Hyperconjugation)

Column-I (Compound) Column-II (Properties)
(A) (P) o-p directing
(B) (Q) m-directing
(C) (R) Activating towards electrophile
(D) (S) Deactivating towards electrophile
APNI KAKSHA 84
Column-I (Reaction) Column-II (Product & its property)
(A) (P) Tropylium ion
(B) (Q) Benzaldehyde
(C) (R) Product can oxidise by KMnO4 /H +
AlCl3
(D) C6H6 + CO + HCl ⎯⎯ ⎯→? (S) Aromatic product obtained

Column-I (Reactions) Column-II (Intermediate formed or type of reaction)
(A) (P) Product obtained as racemic mixture
(B) (Q) Substitution reaction
(C) (R) Nu⊖ Addition takes place during reaction
(D) (S) Carbocation intermediate
(T) Carbanion intermediate
APNI KAKSHA 85
EXERCISE #III
Q.1 Write the most stable resonating structure for the cyclohexadienyl anion formed by reaction of
methoxide ion with o-fluoronitrobenzene.
Q.2 Write the principal organic product in each of the following reactions:
Q.3
Q.4
Q.5 Reaction of 1,2,3-tribromo-5-nitrobenzene with sodium ethoxide in ethanol gave a single product,
C8 H7 Br2 NO3 , in quantitative yield. Suggest a reasonable structure for this compound.
Q.6 Offer an explanation for the observation that 4-chloropyridine is more reactive toward nucleophiles
than 3-chloropyridine.
Q.7 The dichlorocarbene reacts with phenol in base where as it doesn't reacts with benzene explain.
APNI KAKSHA 86
Q.8 Find out the products in given reaction sequence:
Q.9
Q.10 Compare the given characteristics of aniline and cyclohexanamine :

(i) Both are primary amine
(ii) Both can be acylated by RCOCl
(iii) Both reacts with CHCl3 /KOH
(iv) Both reacts with NaNO2 + HCl at 0 − 5∘ C
(v) Both reacts with PhSO2 Cl to give a compound which is soluble in KOH
(vi) Both gives coupling reaction with phenol
(vii)Both gives electrophilic substitution reaction
How many of the given characteristics are correct?
Q. 11 Number of compounds which can show faster rate of nucleophilic substitution of halogen than
Q.12 Number of possible monochlorinated isomer of R.
APNI KAKSHA 87
Q.13 Identify total number of reactions incorrectly match with its product?
APNI KAKSHA 88
For given reaction sequence molecular formula for compound ' U ' is C7 H6 O2 & P gives negative
Fehling test.
Q.14 Compound which is not a hydrocarbon

(A) W (B) R (C) T (D) V
Q.15 Compound S is:
(A) CH3 − CH = O (B) Ph − CH = O (C) (D)
APNI KAKSHA 89
EXERCISE # IV (MAIN)
Q.1 Reaction - [AIEEE-2002]
Primary amine +CHCl3 + KOH → product, here product will be -
(A) Cyanide (B) Isocyanide (C) Amine (D) Alcohol
Q.2 The compound formed in the positive test for nitrogen with the Lassaigne solution of an organic
compound is - [AIEEE-2004]
(A) Fe4 [Fe(CN)6 ]3 (B) Na3 [Fe(CN)6 ] (C) Fe(CN)3 (D) Na4 [Fe(CN)5 )NOS]
Q.3 Which one of the following methods is neither meant for the synthesis nor for separation of
amines [AIEEE-2005]
(A) Hofmann method (B) Hinsberg method
(C) Curtius reaction (D) Wurtz reaction
Q.4
The electrophile involved in the above reaction is [AIEEE-2006]
Θ ⊕
(A) dichlorocarbene (CHCl2 ) (B) trichloromethyl anion (CHCl2 )
⊕
(C) formyl cation (: CHCl2 ) (D) dichloromethyl cation (CHO)
Q.5 In the chemical reaction, CH3 CH2 NH2 + CHCl3 + 3KOH → (A) + (B) + 3H2 O, the compounds (A)
and (B) are respectively - [AIEEE-2007]
(A) C2 H5 CN and 3KCl (B) CH3 CH2 CONH2 and 3KCl
(C) C2 H5 NC and K 2 CO3 (D) C2 H5 NC and 3KCl
Q.6 The electrophile, E ⊕ attacks the benzene ring to generate the intermediate 𝜎-complex. Of the
following, which 𝜎-complex is of lowest energy? [AIEEE-2008]
(A) (B) (C) (D)
Q.7 In the chemical reactions, [AIEEE-2010]
the compounds 'A' and 'B' respectively are :-

(A) Nitrobenzene and chlorobenzene (B) Nitrobenzene and fluorobenzene
(C) Phenol and benzene (D) Benzene diazonium chloride and fluorobenzene
APNI KAKSHA 90
Q.8 In the chemical reactions
the compounds A and B respectively are: [AIEEE-2011]
(A) Fluorobenzene and phenol (B) Benzene diazonium chloride and benzonitrile
(C) Nitrobenzene and chlorobenzene (D) Phenol and bromobenzene
Q.9 An organic compound A upon reacting with NH3 gives B. On heating, B gives C. C in presence of
KOH reacts with Br2 to give CH3 CH2 NH2 . A is:- [JEE(Main)-2013]
(A) CH3 COOH (B) CH3 CH2 CH2 COOH
(C) (C) CH3 CH2 COOH
Q.10 The gas leaked from a storage tank of the Union Carbide plant in Bhopal gas tragedy was:
[JEE(Main)-2013]
(A) Methylisocyanate (B) Methylamine
(C) Ammonia (D) Phosgene

Q.11 On heating an aliphatic primary amine with chloroform and ethanolic potassium hydroxide, the
organic compound formed is :- [JEE(Main)-2014]
(A) An alkyl cyanide (B) An alkyl isocyanide

(C) An alkanol (C) An alkanediol
Q.12 Sodium phenoxide when heated with CO2 under pressure at 125∘ C yields a product which on
acetylation produces C. [JEE(Main)-2014]
the product E is:-
(A) (B) (C) (D)
APNI KAKSHA 91
Q.13 In the reaction [JEE(Main)-2015]
the product E is:-
(A) (B)
(C) (D)
Q.14 In the following sequence of reactions: [JEE(Main)-2015]

KMnO4 SOCl2 H2 /Pd
Toluene ⎯⎯⎯ → A ⎯⎯⎯ →B ⎯⎯⎯
BaSO4
→C the product C is:-
(A) C6 H5 CH2 OH (B) C6 H5 CHO (C) C6 H5 COOH (D) C6 H5 CH3

Q.15 Which of the following compounds will significant amont of meta product during mono-nitration
reaction? [JEE(Main)-2017]
(A) (B) (C) (D)
Q.16 Phenol react with methyl chloroformate in the presence of NaOH to form product A. A reacts with
Br2 to form product B. A and B are respectively. IIT 2018
(A) (B)
(C) (D)
APNI KAKSHA 92
Q.17 Phenol on treatment with CO2 in the presence of NaOH followed by acidification produces
compound X as the major product. X on treatment with (CH3 CO)2 O in the presence of catalytic
amount of H2 SO4 produces IIT 2018
(A) (B) (C) (D)
Q.18 The major product of the following reaction is : [JEE MAIN-2019]
(A) (B) (C) (D)

Q.19 The compounds A and B in the following reaction are, respectively: [JEE MAIN-2019]
(A) A = Benzyl alcohol, B = Benzyl isocyanide

(B) A = Benzyl alcohol, B = Benzyl cyanide
(C) A = Benzyl chloride, B = Benzyl cyanide
(D) A = Benzyl chloride, B = Benzyl isocyanide
Q.20 The major product of the following reaction is: [JEE MAIN-2019]
(A) (B) (C) (D)
APNI KAKSHA 93
Q.21 The products formed in the reaction of cumene with 𝑂2 followed by treatment with dil. HCl are:
[JEE MAIN-2019]
(A) (B)
(C) (D)
Q.22 The major product obtained in the following reaction is: [JEE MAIN-2019]
(A) (B)
(C) (D)
(A) (B)
(C) (D)
APNI KAKSHA 94
Q.24 What will be the major product in the following mononitration reaction? [JEE MAIN-2019]
(A) (B)
(C) (D)
(A) (B) (C) (D)
(A) (B)
(C) (D)
APNI KAKSHA 95
(A) (B)
(C) (D)
Q.28 Among the following four aromatic compounds, which one will have the lowest melting point?
[JEE MAIN-2019]
(A) (B) (C) (D)
(A) (B)
(C) (D)
(A) (B) (C) (D)
APNI KAKSHA 96
31. The increasing order of the reactivity of the following compounds towards electrophilic
aromatic substitution reactions is: [JEE MAIN-2019]
(A) III < II < I (B) I < III < II (C) II < I < III (D) III < I < II
32. The major product obtained in the given reaction is: [JEE MAIN-2019]
(A) (B)
(C) (D)
33. The major product ' Y ' in the following reaction is: [JEE MAIN-2019]
(A) (B) (C) (D)
34. The major product of the following reactions is: [JEE MAIN-2019]
APNI KAKSHA 97
(A) (B) (C) (D)
35. The major products of the following reaction are: [JEE MAIN-2019]
(A) and Methanol (B) and Methanol
(C) and Formic acid (D) and Formic acid
36. Benzene diazonium chloride on reaction with aniline in the presence of dilute hydrochloric acid
gives: [JEE MAIN-2019]
(A) (B)
(C) (D)
37. Coupling of benzene diazonium chloride with 1-naphthol in alkaline medium will give:
[JEE MAIN-2019]
(A) (B) (C) (D)
APNI KAKSHA 98
38. The major product of the following reaction is:
(A) (B)
(C) (D)
39. Polysubstitution is a major drawback in: [JEE MAIN-2019]

(A) Friedel Craft's alkylation (B) Friedel Craft's acylation
(C) Acetylation of aniline (D) Reimer Tiemann reaction
(A) (B)
(C) (D)
41. The major product obtained in the following reaction is: [JEE MAIN-2019]
(A) (B) (C) (D)
APNI KAKSHA 99
(A) (B) (C) (D)
43. Aniline dissolved in dilute HC1 is reacted with sodium nitrite at 0∘ C. This solution was added
dropwise to a solution containing equimolar mixture of aniline and phenol in dil. HCl. The
structure of the major product is: [JEE MAIN-2019]
(A) (B)
(C) (D)
44. The increasing order of reactivity of the following compounds towards aromatic electrophilic
substitution reaction is: [JEE MAIN-2019]
(a) (b) (c) (d)
(A) a < b < c < d (B) d < b < a < c (C) d < a < c < b (D) b < c < a < d
(A) (B) (C) (D)
APNI KAKSHA 100

46. p-Hydroxybenzophenone upon reaction with bromine in carbon tetrachloride gives:
[JEE MAIN-2019]
(A) (B)
(C) (D)
47. The major product of the following reaction is: [JEE-MAIN 2019]
(A) (B) (C) (D)
(A) (B)
(C) (D)
APNI KAKSHA 101

49. The major product of the following reaction is : [JEE-MAIN 2019]
(A) (B) (C) (D)
50. Among the following four aromatic compounds, which one will have the lowest melting point?
[JEE-MAIN 2019]
(A) (B)
(C) (D)
APNI KAKSHA 102

(A) and Methanol (B) and Methanol
(C) and Formic acid (D) and Formic acid
53.
Mixture of above three organic compound was subjected to aq NaHCO3 and followed by dil NaOH.
compounds which will be soluble in given solvent will be: [JEE-MAIN 2020]
(A) x in aq NaHCO3 and y in dil. NaOH. (B) x in aq NaHCO3 and z in dil. NaOH.
(C) y in aq NaHCO3 and x in dil. NaOH. (D) y is aq NaHCO3 and z in dil. NaOH.
54. Which of the following reactions are possible? [JEE-MAIN 2020]
(A)
(B)
APNI KAKSHA 103

(C)
(D)
(A) A, B, C (B) B, D (C) A, C, D (D) A, C

55. Reagent used for the given conversion is: [JEE-MAIN 2020]
(A) H2 , Pd (B) B2 H6 (C) NaBH4 (D) LiAlH4

56. How many atoms lie in the same plane in the major product (C)? [JEE-MAIN 2020]
CH3Cl(1eq.)
A ⎯⎯⎯
Cutube
→B ⎯⎯⎯⎯AlCl3
→C
(Where A is the alkyne of lowest molecular mass)

(A) (B)
(C) (D)
APNI KAKSHA 104

58. Three isomers A, B and C ( mol. formula C8 H11 N) give the following results [JEE-MAIN 2020]
A and C ⎯⎯⎯⎯→
Diazotization
(ii)Oxidation
(i)Hydrolysis R(ProductofA)
(KMnO4 +H+ )
P + Q→ +
S(ProductofC)
R has lower boiling point than S
C6H5SO2Cl
B ⎯⎯⎯⎯ → alkali-insoluble product
A, B and C, respectively are
(A)
(B)
(C)
(D)
59. In the following reaction sequence, [C] is [JEE-MAIN 2020]
(A)
(B)
APNI KAKSHA 105

(C)
(D)
60. Which of the following reactions are possible? [JEE-MAIN 2020]
(A)
(B)
(C)
(D)
(A) A, B, C (B) B, D (C) A, C, D (D) A, C

61. Which of these will produce the highest yield in Friedel Craft reaction? [JEE-MAIN 2020]
(A) (B) (C) (D)
62. In the following reaction the reason why meta-nitro product also formed is: [JEE-MAIN 2021]
APNI KAKSHA 106

(A) Formation of anilinium ion

(B) −NO2 substitution always takes place at meta-position
(C) low temperature
(D) −NH2 group is highly meta-directive
63. The correct order of the following compounds showing increasing tendency towards nucleophilic
substitution reaction is : [JEE-MAIN 2021]
(A) (iv)<(i)<(iii)<(ii) (B) (iv) < (i) < (ii) < (iii)
(C) (i)<(ii)<(iii)<(iv) (D) (iv) < (iii) < (ii) < (i)
(A) (B)
(C) (D)
APNI KAKSHA 107

EXERCISE # IV A (ADVANCE)
Q.1 The chlorination of toluene in presence of ferric chloride gives predominatly: [JEE 1986]
(A) Benzyl chloride (B) m-Chlorotoluene
(C) Benzal chloride (D) o-and p-Chlorotoluene
Q.2 Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl
halide due to [JEE 1990]
(A) The formation of less stable carbonium ion
(B) Resonance stabilization
(C) Longer carbon-halogen bond
(D) The inductive effect
Q.3 The most basic compound among the following is: [JEE 1990]
(A) Benzylamine (B) Aniline (C) Acetaniline (D) p-Nitro aniline
Q.4 Chlorination of toluene in the presence of light and heat followed by treatment with aqueous
NaOH gives: [JEE 1990]
(A) o-Cresol (B) p-Cresol
(C) 2,4-Dihydroxytoluene (D) Benzoic acid
Q.5 When nitrobenzene is treated with Br2 in presence of FeBr3 the major product formed is m-
bromonitrobenzene. Correct statements are : [JEE 1992]
(A) The electron density on meta carbon is more than on ortho and para position.
(B) The intermediate carbonium ion formed after initial attack of Br + attack the meta position
is least destabilized.
(C) Loss of aromaticity when Br + attacks at the ortho and para positions and not at meta
position
(D) Easier loss of H + to regain aromaticity form the meta position than from ortho and para
position.
Q.6 Reaction of R-CO- NH2 with a mixture of Br2 and KOH gives R − NH2 as the main product. The
intermediates involved in this reaction are: [JEE 1992]
(A) R − CO − NHBr (B) RNHBr (C) R − N = C = O (D) R.CO.NBr
Q.7 Choose the correct statement from the ones given below for two aniline in: [JEE 1993]
APNI KAKSHA 108

(A) II is not an acceptable canonical structure because carbonium ions are less stable than
ammonium ions
(B) II is not an acceptable canonical structure because it is non aromatic
(C) II is not an acceptable canonical structure because the nitrogen has 10 valence electrons
(D) II is an acceptable canonical structure
Q.8 Most stable carbonium ion is: [JEE 1995]
(A) p − NO2 − C6 H4 − + CH2 (B) C6 H5 + CH2
(C) p − Cl − C6 H4 + + CH2 (D) p − CH3 O − C6 H4 − +
CH2
Q.9 Arrange in order of decreasing trend towards 𝑆𝐸 reactions: [JEE 1995]
(I) Chlorobenzene (II) Benzene (III) Anilinium chloride (IV) Toluene
(A) II > I > III > IV (B) III > I > II > IV (C) IV > II > I > III (D) I > II > III > IV
Q.10 Among the following statements on the nitration of aromatic compounds, the false one is:
[JEE 1997]
(A) The rate of benzene is almost the same as that of hexadeuterobenzene
(B) The rate of nitration of toluene is greater than that of benzene.
(C) The rate of nitration of benzene is greater than that of hexadeuterobenzene
(D) Nitration is an electrophilic substitution reaction
Q.11 Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO3 and conc. H2 SO4 . In
the nitrating mixture HNO3 acts as a: [JEE 1997]
(A) Base (B) Acid (C) Reducing agent (D) Catalyst
Q.12 Benzyl chloride (C6 H5 CH2 Cl) can be prepared from toluene by chlorination with: [JEE 1998]
(A) SO2 Cl2 hv (B) SOCl2 (C) Cl2 hv (D) NaOCl
Q.13 The most unlikely representation of resonance structure of p-nitrophenoxide ion is: [JEE 1998]
(A) (B) (C) (D)
Q.14 Benzenediazonium chloride on reaction with phenol in weakly basic medium gives: [JEE 1998]
(A) Diphenyl ether (B) p-hydrooxyazobenzene
(C) Chlorobenzene (D) Benzene
APNI KAKSHA 109

Q.15 A solution of (+) -1-chloro-1-phenylethane in toluene racemises slowly in the presence of small
amount of SbCl5 , due to the formation of: [JEE 1999]
(A) Carbanion (B) Carbene (C) Free-radical (D) Carbocation
Q.16 Toluene, when treated with Br2 /Fe, gives p-bromotoluene as the major product, because the
CH3 group: [JEE 1999]
(A) is para directing (B) is meta directing
(C) activates the ring by hyperconjugation (D) deactivates the ring
Q.17 Amongst the following the strongest base is: [JEE 2000]
(A) C6 H5 NH2 (B) p − O2 NC6 H4 NH2
(C) m − O2 NC6 H4 NH2 (D) C6 H5 CH2 NH2
Q.18 Identify the correct order of reactivity in electrophilic substitution reactions of the following
compounds: [JEE 2002]
(I) (II) (III) (IV)
(A) I > II > III > IV (B) IV > III > II > I (C) II > I > III > IV (D) II > III > I > IV
Q.19 [JEE 2003]
(A) (B)
(C) (D)
Q.20 [JEE 2004]
Major product of above reaction is:
(A) (B) (C) (D)
APNI KAKSHA 110

Q.21 Which of the following is obtained when 4-Methylbenzenesulphonic acid is hydrolysed with
excess of sodium acetate? [JEE 2005]
(A) (B)
(C) (D)
Q.22 CH3 NH2 + CHCl3 + KOH → Nitrogen containing compound +KCl + H2 O. Nitrogen containing
compound is [JEE 2006]
+ +
(A) CH3 − C ≡ N ̅≡C
(B) CH3 − NH − CH3 (C) CH3 − N (D) CH3 N ≡ C̅
Q.23 [JEE 2006]
The major products P and Q are
(A) (B)
(C) (D)
Question No. 24 to 26 ( 3 questions)

Comprehension I
RCONH2 is converted into RNH2 by means of Hofmann bromamide degradation.
In this reaction, RCONHBr is formed from which this reaction has derived its name. Electron
donating group at phenyl activates the reaction. Hofmann degradation reaction is an
intramolecular reaction.
Q.24 How can the conversion of (i) to (ii) be brought about? [JEE 2006]
(A) KBr (B) KBr + CH3 Ona (C) KBr + KOH (D) Br2 + KOH
APNI KAKSHA 111

Q.25 Which is the rate determining step in Hofmann bromamide degradation? [JEE 2006]
(A) Formation of (i) (B) Formation of (ii)
(C) Formation of (iii) (D) Formation of (iv)
Q.26 What are the constituent amines formed when the mixture of (i) and (ii) undergoes Hofmann
bromamide degradation? [JEE 2006]
(A)
(B)
(C)
(D)
Paragraph for Question Nos. 27 to 30 (4 questions)

Riemer-Tiemann reaction introduces an aldehyde group, on to the aromatic ring of phenol, ortho
to the hydroxyl group. This reaction involves electrophilic aromatic substitution. This is a general
method for the synthesis of substituted salicylaldehydes as depicted below.
Q.27 Which one of the following reagents is used in the above reaction? [JEE 2007]
(A) aq. NaOH + CH3 Cl (B) aq. NaOH + CH2 Cl2
(C) aq. NaOH + CHCl3 (D) aq. NaOH + CCl4
Q.28 The electrophile in this reaction is [JEE 2007]
(A) : CHCl (B) +
CHCl2 (C) : CCl2 (D) ⋅ CCl3
APNI KAKSHA 112

Q.29 The structure of the intermediate I is [JEE 2007]
(A) (B) (C) (D)
Q.30 In the following reaction, [JEE 2007]
the structure of the major product ' X ' is
(A) (B)
(C) (D)
Q.31 Statement - 1: Bromobenzene upon reaction with Br2 /Fe gives 1, 4-dibromobenzene as the major
product. [JEE 2008]
Statement-2: In bromobenzene, the inductive effect of the bromo group is more dominant than
the mesomeric effect in directing the incoming electrophile.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1
Statement 1
(C) Statement-1 is True, Statement-2 is False
(D) Statement- 1 is False, Statement- 2 is True
Q.32 Statement-1 : Aniline on reaction with NaNO2 /HCl at 0∘ C followed by coupling with 𝛽-naphthol
gives a dark blue coloured precipitate.
Statement-2 : The colour of the compound formed in the reaction of aniline with NaNO2 /HCl at 0∘
followed by coupling with 𝛽-naphthol is due to the extended conjugation.
(A) Statement-1 is True, Statement-2 is True ; Statement-2 is a correct explanation for Statement-1
(B) Statement-1 is True, Statement-2 is True ; Statement-2 is NOT a correct explanation for
Statement 1
(C) Statement-1 is True, Statement-2 is False
(D) Statement-1 is False, Statement-2 is True [JEE 2008]
APNI KAKSHA 113

Q.33 In the reaction the intermediate(s) is(are)- [JEE 2009]
(A) (B) (C) (D)
Q.34 The compounds P, Q and S [JEE 2009]
were separately subjected to nitration using HNO3 /H2 SO4 mixture. The product formed in each
case respectively, is
(A)
(B)
(C)
(D)
Q.35 The correct acidity order of the following is: [JEE 2009]
(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)
APNI KAKSHA 114

Q.36 In the following carbocation, H/CH3 that is most likely to migrate to the positively charged carbon
is: [JEE 2009]
(A) CH3 at C − 4 (B) H at C − 4 (C) CH3 at C − 2 (D) H at C − 2

Q.37 Match the reactions in Column-I with appropriate options in Column-II. [IIT-JEE-2010]
Column-I Column-II
(A) (P) Racemic mixture
(B) (Q) Addition reaction
(C) (R) Substitution reaction
(D) (S) Coupling reaction
(T) Carbocation intermediate
The structure of the Product T is: [JEE 2010]
(A) (B)
(C) (D)
Q.39 Among the following compounds, the most acidic is [JEE 2011]
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid
APNI KAKSHA 115
Q.40 Match the reactions in Column-I with appropriate types of step/reactive intermediate involved
in these reactions as given in Column-II [IIT-JEE-2012]
Column-I Column-II
(A) (P) Nucleophilic substitution
(B) (Q) Electrophilic substitution
(C) (R) Dehydration
(D) (S) Nucleophilic addition
(R) Carbanion
Q.41 Among P, Q, R and S, the aromatic compound(s) is / are: [JEE 2013]
(A) P (B) Q (C) R (D) S

Q.42 The major product(s) of the following reaction is (are) - [JEE 2013]
(A) P (B) Q (C) R (D) S

APNI KAKSHA 116
Q.43 In the following reaction, the product (s) formed is (are) [JEE 2013]
(A) P (major) (B) Q (minor) (C) R (minor) (D) S (major)

Paragraph for Question 44 and 45
P&Q are isomers of dicarboxylic acid C4 H4 O4 . Both decolourize Br2 /H2 O, On heating P forms
the cyclic anhydride.
Upon treatment with dilute alkaline KMnO4 , P as well as Q could produce one or more than one
from S, T and U. [JEE 2013]
Q.44 In the following reaction sequences V and W are, respectively -
(A) (B)
(C) (D)
APNI KAKSHA 117

Q.45 Compounds formed from P and Q are respectively
(A) Optically active S and optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S
Q.46 In the reaction shown below, the major product(s) formed is / are: [JEE 2014]
(A) (B)
(C) (D)
Q.47 The reactivity of compound Z with different halogens under appropriate conditions is given
below: [JEE 2014]
The observed pattern of electrop hilic substitution can be explained by -

(A) The steric effect of the halogen
(B) The steric effect of the tert-butyl group
(C) The electronic effect of the phenolic group
(D) The electronic effect of the turt-butyl group
APNI KAKSHA 118

Q.48 Match the four starting materials (P, Q, R, S) given in List I with the corresponding reaction
scheme (I, II, III, IV) provided in List - II and select the correct answer using the code given below
in lists. [JEE 2014]
Code :
P Q R S
(A) 1 4 2 3
(B) 3 1 4 2
(C) 3 4 2 1
(D) 4 1 3 2
APNI KAKSHA 119

Q.49 The major product 𝑈 in the following reactions is: [IIT 2015]
(A) (B)
(C) (D)
Q.50 In the following reactions, the major product W is: [IIT 2015]
(A) (B)
(C) (D)
APNI KAKSHA 120

Q.51 Among the following the number of reaction(s) that produce(s) benzaldehyde is: [IIT 2015]
I. II.
III. IV.
Q.52 The correct statements(s) about of the following reaction sequence is(are) [IIT 2016]
(A) R is steam volatile

(B) Q gives dark violet coloration with 1% aqueous FeCl3 solution
(C) S gives yellow precipitate with 2, 4, -dinitrophenylhydrazine
(D) S gives dark violet coloration with 1% aqueous FeCl3 solution
Q.53 The product(s) of the following reaction sequence is(are) [IIT 2016]
(A) (B) (C) (D)
Q.54 Among the following reaction(s) which gives (give) tert-butyl benzene as the major product
is(are) [IIT 2016]
(A) (B)
(C) (D)
APNI KAKSHA 121

Q.55 The major product of the following reaction is [IIT 2017]
(A) (B) (C) (D)
Answer Q.56, Q.57 and Q.58 by appropriately matching the information given in the three
columns of the following table. [IIT 2017]
Column-1, 2 and 3 contain starting materials, reactions conditions, and type of
Column-1 Column-2 Column-3
(I) Toluene (i) NaOH/Br2 (P) Condensation
(II) Acetophenone (ii) Br2 /hv (Q) Carboxylation
(III) Benzaldehyde (iii) (CH3 CO)2 O/CH3 COOK (R) Substitution
(IV) Phenol (iv) NaOH/CO2 (S) Haloform
Q.56 For the synthesis of benzoic acid, the only CORRECT combination is
(A) (III) (iv) (R) (B) (IV) (ii) (P) (C) (I) (iv) (Q) (D) (II) (i) (S)
Q.57 The only CORRECT combination in which the reaction proceeds through radical mechanism is
(A) (I) (ii) (R) (B) (II) (iii) (R) (C) (III) (ii) (P) (D) (IV) (i) (Q)
Q.58 The only CORRECT combination that give two different carboxylic acids is
(A) (IV) (iii) (Q) (B) (III) (iii) (P) (C) (II) (iv) (R) (D) (I) (i) (S)
The reaction of compound P with CH3 MgBr (excess) in (C2 H5 )2 O followed by addition of H2 O
gives Q. The compound Q on treatment with H2 SO4 at 0∘ C gives R. The reaction of R with
CH3 COCl in the presence of anhydrous AlCl3 in CH2 Cl2 followed by treatment with H2 O
produces compound S. [Et in compound P is ethyl group] [IIT 2017]
APNI KAKSHA 122

Q.59 The reactions, Q to R and R to S, are
(A) Dehydration and Friedel-Crafts acylation
(B) Friedel-Crafts alkylation, dehydration and Friedel-Crafts acylation
(C) Aromatic sulfonation and friedel-Crafts acylation
(D) Friedel-Crafts alkylation and Friedel-Crafts acylation
Q.60 The product 𝐒 is
(A) (B)
(C) (D)
PARAGRAPH Q.61 to Q.62

Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3 /CuCl followed by reaction
with Ac2 O/NaOAc gives compound X as the major product. Compound 𝐗 upon reaction with Br2 /
Na2 CO3 , followed by heating at 473 K with moist KOH furnishes 𝐘 as the major product. Reaction of
𝐗 with H2 /Pd − C, followed by H3 PO4 treatment gives Z as the major product. [IIT 2018]
Q.61 The compound 𝐘 is
(A) (B)
(C) (D)
Q.62 The compound 𝐘 is
(A) (B) (C) (D)
APNI KAKSHA 123

Q.63 Aniline reacts with mixed acid (conc. HNO3 and conc. H2 SO4 ) at 288 K to give 𝐏(51%), 𝐐(47%)
and 𝐑(2%). The major product(s) of the following reaction sequence is (are) [IIT 2018]
(A) (B) (C) (D)
Q.64 In the following reaction sequence, the amount of 𝐃 (in g ) formed from 10 moles of
acetophenone is
(Atomic weights in gmol−1 : H = 1, C = 12, N = 14, O = 16, Br = 80. The yield (%)
corresponding to the product in each step is given in the parenthesis) [IIT 2018]
Q.65 Schemes 1 and 2 describe the conversion of 𝑃 to 𝑄 and 𝑅 to 𝑆, respectively. Scheme 3 describes
the synthesis of T from Q and S. The total number of Br atoms in a molecule of T is [IIT 2019]
Scheme 1:
Scheme 2:
Scheme 3:
()i NaOH
S ⎯⎯⎯
( ii) Q → T
( major )
APNI KAKSHA 124

Q.66 Choose the correct option(s) for the following reaction sequence [IIT 2019]
Consider Q, R and S as major products
(A) (B)
(C) (D)
Q.67 Choose the correct option(s) that gives(s) an aromatic compound as the major product [IIT 2019]
(A) (B)
(C) (D)
Q.68 Considering the following reaction sequence,
APNI KAKSHA 125

Q.69 Considering the following reaction sequence, the correct statement(s) is (are)
(A) Compounds P and Q are carboxylic acids.

(B) Compounds S decolorizes bromine water.
(C) Compounds P and S react with hydroxylamine to give the corresponding oximes.
(C) Compound R reacts with dialkylcadmium to give the corresponding tertiary alcohol.
Q.70 In the following reactions, P, Q, R and S are the major products.
The correct statement(s) about P, Q, R, and S is(are)

(A) P and Q are monomers of polymers dacron and glyptal, respectively.
(B) P, Q, and R are dicarboxylic acids.
(C) Compounds Q and R are the same.
(D) R does not undergo aldol condensation and S does not undergo Cannizzaro reaction.
APNI KAKSHA 126

EXERCISE # IV B (ADVANCE)
Q.1 [JEE 1992]
() 2
i Br ,Heat ,Light
Q.2 C6H5C2H5 ⎯⎯⎯⎯⎯→
( ii ) NaCN [JEE 1994]
Q.3 An organic compound (A). C8 H6 on treatment with dilute sulphuric acid containing mercuric
sulphate gives a compound (B), which can also be obtained from a reaction of benzene with an
acid chloride in the presence of anhydrous aluminium chloride. The compound (B), when treated
with iodine in aqueous KOH, yields (C) and a yellow compound (D). Identify (A), (B), (C) and (D)
with justification. Show how (B) is formed from (A) ? [JEE 1994]
Q.4 Toluene reacts with bromine in the presence of light to give benzyl bromine while in presence
of FeBr3 it gives p-bromotoluene. Give explanation for the above observations. [JEE 1996]
Q.5 Show the steps to carry out the following transformations: [JEE 1998]
(a) Ethylbenzene ⟶ benzene (b) Ethylbenzene ⟶ 2-phenylpropionic acid
alcoholic KOH, heat
Q.6 C6 H5 CH2 CHClC6 H5 ⟶ (A) + (B) [JEE 1998]
(Cis and trans forms)
Q.7 Normally, benzene gives electrophilic substitution reaction rather than thus electrophilic
addition reaction although it has double bonds. [JEE 2000]
Q.8 How would you synthesis 4 methoxyphenol from bromobenzene in NOT more than five steps?
State clearly the reagents used in each step and show the structures of the intermediate
compounds in your synthetic scheme. [JEE 2001]
Q.9 Carry out following conversions in 3 or less steps. [JEE 2003]
Q.10 A compound C9 H7 O2 Cl exists in keto form A and enolic form B. Enolic form B predominates at
equilibrium. On oxidation with KMnO4 it gives m-chlorobenzoic acid. Give structures of A andB.
[JEE 2003]
Q.11 7-bromo-1, 3, 5-cycloheptatriene is ionic compound, whereas 5-bromo-1,3-cyclopentadiene
can't ionise even in the presence of Ag ⊕ , Explain why? [JEE 2004]
APNI KAKSHA 127

Q.12 Give reasons: [JEE 2005]
(a)
(b)
(c)
(d)
Q.13
Find A, B, C and D. Also write equations 𝐴 to 𝐵 and 𝐴 to 𝐶. [JEE 2005]

Q.14 The maximum number of isomers (including stereoisomers) that are possible on mono-
chlorination of the following compounds, is [JEE 2011]
Q.15 In the following reaction, compound Q is obtained from compound P via an ionic intermediate.
What is the degree of unsaturation of Q?

Q.16 The weight percentage of hydrogen in Q, formed in the following reaction sequence, is
[Given: Atomic mass of H = 1, C = 12, N = 14, O = 16, S = 32, Cl = 35]

APNI KAKSHA 128
ANSWER KEY
EXERCISE-I
1. B 2. C 3. C 4. C 5. C 6. B 7. D
8. B 9. B 10. D 11. A 12. C 13. A 14. B
15. A 16. B 17. B 18. D 19. B 20. B 21. A
22. A 23. B 24. C 25. A 26. C 27. B 28. B
29. B 30. A 31. D 32. C 33. C 34. D 35. D
36. A 37. D 38. C 39. C 40. A 41. A 42. B
43. C 44. A 45. D 46. A 47. A 48. C 49. A
50. B 51. C
EXERCISE-II
1. ABCD 2. ABD 3. BD 4. BCD 5. ABC 6. ABD 7. BD
8. CD 9. CD 10. BC 11. BCD 12. AB 13. ABCD 14. ABC
15. AC 16. ABD 17. BCD 18. ABC 19. ABC 20. ABCD 21. C
22. B 23. A 24. ACD 25. BC 26. ABD 27. A 28. A
29. B 30. A 31. A→Q; B→PRS; C→RS; D→PQRS
32. A→Q; B→P; C→R; 33. A→PS; B→PR; C→QS; D→PR
34. A→QRS; B→PRS; C→RS; D→QRS; 35. A→RT; B→RS; C→QS; D→PR;
APNI KAKSHA 129

EXERCISE-III
Q.1
Q.2
Q.3
Q.4
Q.5
Q.7 Due to more electron density

Q.8
Q.9
Q.10 5 Q.11 3 Q.12 4 Q.13 7 Q.14 B Q.15 C
APNI KAKSHA 130

EXERCISE-IV (JEE-MAIN)
1. 2 2. 1 3. 4 4. 1 5. 4
6. 2 7. 4 8. 2 9. 4 10. 1
11. 2 12. 3 13. 1 14. 2 15. 3
16. 4 17. 2 18. 2 19. 4 20. 3
21. 1 22. 2 23. 1 24. 2 25. 4
26. 2 27. 3 28. 1 29. 4 30. 4
31. 4 32. 4 33. 1 34. 2 35. 3
36. 1 37. 2 38. 2 39. 1 40. 4
41. 2 42. 2 43. 3 44. 3 45. 3
46. 3 47. (C) 48. (B) 49. (A) 50. (4)
51. (1) 52. (D) 53. (A) 54. (B) 55. (B)
56. (13.00) 57. (B) 58. (D) 59. (B) 60. (B)
61. (C) 62. (A) 63. (C) 64. (D)
EXERCISE-IV- A (JEE-ADVANCE)
1. D 2. B 3. A 4. D 5. AB
6. C 7. C 8. D 9. C 10. C
11. A 12. AC 13. C 14. B 15. D
16. AC 17. D 18. C 19. B 20. D
21. C 22. D 23. C 24. D 25. D
26. B 27. C 28. C 29. B 30. B
31. C 32. D 33. ABC 34. C 35. A
36. D 37. A-RS; B-T; C-PQ; D-R; 38. C 39. C
40. A-RST; B-PS; C-RS; D-QR; 41. ABCD 42. B 43. BD
44. A 45. B 46. A 47. ABC 48. C
49. B 50. A 51. 4 52. BC 53. B
54. BCD 55. C 56. D 57. A 58. B
59. D 60. B 61. C 62. A 63. D
64. 495 65. 4.00 66. 1AB 67. CD 68. (A,B,C)
69. (A, C) 70. (C, D)
APNI KAKSHA 131

68. Sol.
69. Sol.
Opt: - A * Compound P and Q are carboxylic acid

* Compound S do not decolourise bromine water due to absence of (C = C) bond.
* Compound P and S react with hydroxylamine to give the corresponding oximes due
to presence of ketone group.
APNI KAKSHA 132

EXERCISE-IV- B (SUBJECTIVE)
1.
2.
3. (A) (B) (C)
4. In presence of FeBr3 , Br2 produces Br + (an electrophile) which attacks the benzene ring at o-,p-
position to give p-bromotoluene. In presence of light, side chain is attacked to produce benzyl
bromide.
5. (b)
( )
KOH alc.
6. C6H5CH2CHClC6H5 ⎯⎯⎯

⎯→C6H5CH = CHC6H5
(Cisandtransforms)
7. Benzene has resonance stabilization due to delocalisation of 𝜋-electrons. Also during

electrophilic addition reactions, it loses its aromaticity. In electrophilic substitution reaction
aromaticity is retained.
8.
APNI KAKSHA 133

9.
10.
Enol form is more stable due to extended conjugation
11. On ionization 7-bromo-1,3,4-cycloheptatriene gives tropolium ion which is aromatic with 6𝜋

electrons.
5-bromo-1,3-cyclopentadiene can't ionise as it will in that case give highly unstable antiaromatic
cation with 4𝜋 electrons.
12. (a)(i) ;(ii) no reaction due to partial double bond character
(b)(i) +F − is liberated; (ii) Bimomecular mechanism is not possible in (ii) case
(c) (i) Due to presence of lone pair of nitrogen atom NO group is electron donating and ortho,
para directing
(ii) NO2 group is electron withdrawing and meta directing
(d) Due to reduction of central ring, three four membered antiaromatic rings become stable
while on recuction of terminal ring only one antiaromatic ring can be stabilized.
APNI KAKSHA 134

13. (A) H2 SO4 , (B) Br2 , (C) NO⊕
2 , (D)
14. (8)
15. (18)
The total degree of unsaturation =18
16. 1.31⊕⊝
APNI KAKSHA 135

SOLUTION
JEE-MAIN
47.
48.
49.
50. The force of attraction between the molecules affects the melting point of a compound. Polarity
increases the intermolecular force of attraction and as a result increases the melting point.
APNI KAKSHA 136

51.
52.
53.
54. Vinyl halides and aryl halides do not give Friedel craft's reaction.
55. B2 H6 is very selective and usually used to reduce acid to alcohol
APNI KAKSHA 137

56.
57.
Position of electrophilic attack is directed by the electron donating group present in ring.
58.
APNI KAKSHA 138

59.
60. Vinyl halides and aryl halides do not give Friedel craft's reaction.
61. Aniline and phenol form complex with lewis acid so most reactive among the given compounds for
Friedel Craft reaction is chlrobenzene.
62.
63.
64.
APNI KAKSHA 139

(Organic Chemistry) BIOMOLECULES
EXERCISE-I
Q.1 Iso-electric point of alanine is (pH = 6). At which pH, maximum concentration of zwitter ion of
alanine will be present?
(A) pH > 6 (B) pH < 6 (C) pH = 6 (D) pH = 7
Q.2 At iso-electric point :
(A) Concentration of cation is equal to concentration of anion
(B) Net charge is zero
(C) Maximum conc. of di-pole ion (Zwitter ion) will be present
(D) All of the above
Q.3 Which of following amino acid has lowest iso-electric point ?
(A) Glycine (B) Alanine (C) Aspartic acid (D) Lysine
→ ( A ) ⎯⎯⎯⎯→
( ) 3
( B) ; Product (B) of given reaction is :
HgSO4 1 NH + HCN
Q.4 H — C  C — H ⎯⎯⎯
H2SO4 ( 2) H O+
3
(A) Glycine (B) Alanine (C) Valine (D) Leucine

Q.5 Which amino acid does not contain chiral centre?
(A) Valine (B) Leucine (C) Glycine (D) Iso-leucine
Q.6 Which of the following is Sanger reagent ?
(A) 2,4-Di-nitro flurobenzene (B) Phenyl isocyanane
(C) 2,4-Di-nitro chlororbenzene (D) 12,4-Di-nitro-iodobenzene
Q.7 A D-carbohydrate is :
(A) Always dextrorotatory
(B) Always laevorotatrory
(C) Always the mirror of the corresponding L-carbohydrate
(D) None of these
Q.8 The given osazone can be obtained by :
(A) D-glucose (B) D-mannose (C) D-Idose (D) Both (A) & (B)
Q.9 Which of the following pair gives same phenyl osazone?
(A) D-Glucose and D-Allose (B) D-Glucose and D-Altrose
(C) D-Glucose and D-Mannose (D) D-Glucose and D-Talose
APNI KAKSHA 44
Q.10 Which of the following represents the anomer of the compound shown?
(A) (B)
Q.11 For the complex conversion of D-glucose into the corresponding osazone, the minimum number
of equivalents of phenyl hydrzine required is :
(A) Two (B) Three (C) Four (D) Five
Q.12 Which of the following structure is L-arabinose?
(A) (B)
(C) (D)
APNI KAKSHA 45
Q.13 Which one of the statements concerning the equilibrium shown is true?
(A) The two structures are enantiomers of each other. They have equal but oppostie optical
rotations and recemize slowly at room temperature
(B) The two structures are enantiomers of each other. They racemize too rapidly at room
temperature for their optical rotations to be measured
(C) The two structures are diastereomers of each other. Their interconversion is called
mutarotation
(D) The two structures are diastereomers of each other. Their interconversion does not require
breaking and making bonds, only a change in conformation
Q.14 Major product of following reaction is :
(A)
(B)
(C)
(D)
APNI KAKSHA 46
Q.15 What is the structure of L-glucose ?
(A) (B)
Q.16 What is the structure of L-glyceraldehyde?
(A) (B)
(C) (D) Both (A) and (B)
Q.17 the given is enol form of :
(A) D-glucose (B) D-mannose (C) D-fructose (D) All of these

Q.18 D-glucose & D-fructose can be differentiated by :
(A) Fehling solution (B) Tollen's reagent (C) Benedict test (D) Br2 /H2 O
Q.19 D-Glucose exist in x different forms. The value of x (stereoisomer) is :
(A) 2 (B) 3 (C) 4 (D) 5
Q.20
Product (A) of above reaction is :
(A) D-glucose (B) D-fructose (C) D-talose (D) D-idose
Q.21 Which of the following statement is not correct for maltose.
(A) It is a disaccharide (B) It undergoes mutarotation
(C) It is a reducing sugar (D) It does not have hemiacetal group.
APNI KAKSHA 47
Q.22 A compound which does not react with Brady's reagent but decolourise Br2 /H2 O solution is :
(A) (B) (C) (D)

Q.23 Maltose is made up of to two sugars-
(A) Glucose (B) Fructose (C) Glucose & galactose (D) Glucose & fructose
Q.24 D-Ribose when treated with dilute HNO3 forms.
(A) (B)
(C) (D)
Q.25 Consider the given process
and identify the incorrect statement.

(A) Configuration at C − 2 is lost on enolization
(B) I and III are epimers
(C) Proton transfer from water to C − 1 converts ene diol to an aldose.
(D) D-glucose can isomerise to D-fructose through enol intermediate.
Q.26 When methyl D-glucopyranoside is treated with HIO4 its number of mole consumed per mole of
the sugare is -
(A) 2 (B) 3 (C) 4 (D) 5
Q.27 α - amino acid when heated with NaOH/CaO forms -
(A) α, β - unsaturated acid (B) α, β - unsaturated amine
(C) Carboxylic acid (D) Amine
APNI KAKSHA 48
Q.28 The configuration of the C − 2 epimer of D-glucose is-
(A) 2R, 3 S, 4R, 5 S (B) 2 S, 3 S, 4R, 5R (C) 2 S, 3R, 4 S, 5R (D) 2R, 3 S, 4R, 5R
Q.29 Mutarotation involve-
(A) Racemisation (B) Diastereomerisation
(C) Optical resolution (D) Conformational inversion
Q.30 Consider the reaction sequence -
+
PhNHNH2 H3O
Glucose ⎯⎯⎯⎯
excess
→ P ⎯⎯
⎯
→ Q ⎯⎯⎯
Zn
AcOH
→R
The product R is -
(A) Arbinose (B) Sorbitol (C) Fructose (D) Mannose
Q.31 The pH of the solution containing following zwitter ion species is
(A) 4 (B) 5 (C) 7 (D) 9

Q.32 Peptide linkage is –
(A) (B) (C) (D)

Q.33 Same osazone derivative is obtained in case of D-glucose, D-Mannose and D-Fructose due to
(A) The same configuration at C − 5
(B) The same constitution.
(C) The same constitution at C − 1 and C − 2
(D) The same constitution and acid configuration at C-3, C-4, C-5 and C-6 but different
constitution and configuration at C − 1 and C − 2 which becomes identical by osazone
formation.
Q.34 D( − ) − Erythrose ⎯⎯⎯
NaBH4
→( P )
D( − ) − Threose ⎯⎯⎯
NaBH4
→(R )
Which of the following statement is correct about P and R ?
(A) Both are optically active
(B) Both are optically inactive
(C) P is optically inactive and R is optically active
(D) Neither P nor R has asymmetric carbon.
Q.35 The monomer of nucleic acids are held together by
(A) Phosphodiester linkage (B) Amide linkage
(C) Glycosidic linkage (D) Ester linkage
APNI KAKSHA 49
Q.36 Select the incorrect statement about Nylon 2-nylon-6.
(A) It is a copolymer.
(B) It is biodegradable.
(C) It is an alternating polyamide.
(D) It is made up of and H2 N(CH2 )5 COOH.
Q.37 The monomer that can undergo radical, cationic and anionic polymerisation with equal case-
(A) (B) Ph − CH = CH2
(C) CH2 = CH2 (D) CH2 = CH − CN

Q.38 Consider the reaction-
Mixture of A and B can be best separated by -

(A) Steam distillation (B) Vacuum distillation
(C) Fractional distillation (D) Crystallisation
Q.39 Which of the following statements are incorrect :
(A) Copolymer of 1,3-butandiene & acrylonitrile is Buna-S
(B) HDPE is obtained by Ziegler-Natta polymerization
(C) Polymer dacron can be polyester fabric
(D) Phenol & formaldehyde resin is called novolac
Q.40 A segment (X) of cellulose obtained on partial hydrolysis has molecular mass 1476gm . On
complete acidic hydrolysis, mass of the product obtained is 1620gm. Find out the number of
glycosidic linkage(s) present in segment (X) :
(A) 8 (B) 6 (C) 4 (D) 10
Q.41 When solidum extract is treated with FeCl3 solution a blood red coloured is obtained due to the
presence of -
(A) (B)
(C) (D)
Q.42 The monomer that undergo radical polymerisation most easily is
(A) CH2 = CH2 (B) C6 H5 CH = CH2 (C) (D) CH3 − CH = CH2
APNI KAKSHA 50
EXERCISE # II
Q.1 Carbohydrates may be:
(A) Sugars (B) Starch
(C) Polyhydroxy aldehyde/ketones (D) Compounds that can be hydrolysed to sugar
Q.2 Select the correct statement :
(A) Glycosides do not undergo mutarotation
(B) All OH groups of a cyclic monosaccharides are converted to ethers by treatment with base
and an alkyl halide
(C) α-D glucose reacts with Ag 2 O and excess CH3 I to form tetramethyl ether
(D) D-glucose upon treatment with warm HNO3 forms D-glucaric acid
Q.3 "Aspartame" is roughly 100 times as sweet as cane sugar. On complete hydrolysis of aspartame,
products obtained is/are :
(A) (B) (C) CH3 OH (D)
Q.4 Starch molecules are polymer with repeating glucose units. Select the correct statement(s).
(A) Glucose units are joined through α-glycosidic linkage
(B) The branches of amylopectin are linked to the chain with α − 1, 6′ -glycosidic linkages
(C) The linear linkages of amylopectin are formed by α − 1,6-glycosidic bond
(D) Amylose has an unbranched skeleton of glucose molecules with α − 1,4 '-glycosidic linkages
Q.5 Select the correct option.
(A) Isoelectric point is the pH at which an amino acid exists primarily in its neutral form.
(B) Isoelectric point is the average of pK a values of α − COOH amino α − NH3+ groups [ valid only
for neutral amino acid]
(C) Glycine is characterised by two pK a values
(D) For neutral amino acid the concentration of zwitter ion is maximum at its isoelectric point
Q.6 Amino acids are synthesised from
(A) α-Halo acids by reaction with NH3
(B) Aldehydes by reaction with NH3 and cyanide ion followed by hydrolysis
(C) Pyruvic acid is treated with NH3 followed by addition of H2 (Ni)
(D) Alcohols by reaction with NH3 and CN− ion followed by hydroysis.
APNI KAKSHA 51
Q.7 Which of the following carbohydrates developes blue colour on treatment with iodine solution?
(A) Glucose (B) Amylose (C) Starch (D) Fructose
Q.8 Select the correct statement
(A) High density polythene is a linear polymer.
(B) Low density polythene is a branched chain polymer.
(C) Chain growth polymers are also known as addition polymer.
(D) Step growth polymer is also known condensation polymer.
Q.9 Select the correct statement.
(A) Elastomers have the weakest intermolecular forces
(B) Buna-N is example of synthetic copolymer
(C) Some fibres have crystalline nature
(D) Thermoplastic polymers have stronger intermolecular forces than fibres
Q.10 Which of the following options are correct :
(A)
+ AgNO3
(B) Na extract of sample containing chlorobenzene ⎯⎯⎯ → white ppt. of AgCl
(C) Na extract of sample containing chlorobenzene ⎯⎯⎯
+ AgNO3
→ No ppt. of AgCl
(D)
Q.11
Before isolating (P) unreacted Ph − CHO is removed first. Select the correct statement.
(A) P is cinnamaldehyde (B) P is crotonic acid
(C) Removal is done by simple distillation (D) P is cinnamic acid.
Q.12 If on a strand of DNA the base sequence is ATTGACGCAT then the sequence transcription on RNA
would be -
(A)UAACUGCGUA (B) AUUCUGCGUA (C) UAACTGCGUA (D) TAACTGCGTA
Q.13 Select the correct statement among following
(A) Number of chiral atom in α-D-glucose is less than D-glucose
(B) D-glucose and D-fructose give same product with HIO4
(C) D-glucose and D-fructose give same product with H2 NOH
(D) D-glucose and D-fructose form same product with H2 N − NH − Ph
APNI KAKSHA 52
Q.14 The N-base which differenciate DNA with RNA is :
(A) Cytosine (B) Uracil (C) Adenine (D) Guanine
Q.15 Correct statement
(A) Nylon-66 is example of addition polymer
(B) Alanin having pH9 at isoelectric point
(C) Fructose when reacts with fehling solution reddish brown ppt. formed
(D) All of these
Q.16 Match the column :
Column I Column II
(A) Sucrose (P) Two acetals
(B) Maltose (Q) No hemiacetal
(C) Lactose (R) β − 1,4 '-glycosidic bond
(D) Cellulose (S) One of the hydrolysis product is glucose
Q.17 Match the column
Column I Column II
(Component of mixture) (Reagent)
(A) Crystalline Na2 CO3 + (P) Fehling solution
Sodium citrate +CuSO4 (aq. sol.)
(B) CuSO4 + Rochelle Salt +NaOH (Aq. sol.) (Q) Nesseler's Reagent
(C) 10%α - naphthol in alcohol (R) Bennedict's solution
(D) HgCl + KI + KOH (aq. sol.) (S) Molisch's Reagent
APNI KAKSHA 53
EXERCISE # III
Assertion Reason
Q.1 Statement 1 : Furanose ring, like pyranose rings are not planar.
Statement 2 : The most stable conformation of furanose is envelope form.
statement- 1 .
(B) Statement- 1 is true, statement- 2 is true and statement- 2 is NOT the correct explanation for
statement- 1 .
(C) Statement-1 is true, statement- 2 is false.
Q.2 Statement 1 : Bromine water changes glucose to gluconic acid.
Statement 2 : Bromine water acts as oxidising agent.
statement- 1 .
statement-1.
(C) Statement- 1 is true, statement- 2 is false.
Q.3 Statement 1 : All monosaccharide ketoses are reducing sugars.
Statement 2 : Monosaccharide ketose give positive Tollen's and Fehling's test.
statement- 1 .
statement- 1 .
(C) Statement-1 is true, statement- 2 is false.
Comprehension (Q.4 to Q.6)
Consider the following reversible process for a reaction of D-glucose.
APNI KAKSHA 54
Q.4 The structure of intermediate [X] is
(A) (B)
(C) (D)
Q.5 Select the correct option.
(A) (B)
(C) (D)
Q.6 Select the correct statement.

(A) Y is more stable than Z due to H-bond
(B) Y is less stable than Z due to anomeric effect.
(C) Y is more stable than Z due to anomeric effect
(D) Y is less stable than Z due to H-bond.
Comprehension (Q.7 to Q.9)
The monomer (G = Me or Cl) when treated with Zieglar - Natta catalyst undergo
polymerisation in the manner given below –
Q.7 The Zieglar-Natta catalyst is

(A) TiCl4 (B) R 3 Al (C) R 3 Al/TiCl4 (D) R 3 B/TiCl4
Q.8 The polymer obtained when monomeric unit used is

(A) Neoprene (B) Stilbene (C) Styrene (D) Chloropicrin
APNI KAKSHA 55
Q.9 Which of the following statement is not true considering the process given above.
(A) The general class of polymer formed is known as homopolymer
(B) The polymer obtained is stereoregular
(C) Buna- N can be prepared using above process
(D) Synthetic rubber can be formed by above process using 1,3- butadiene.
Match the Column
Q.10 Match the compounds given below existing in equilbrium mixture with their percentage given
in the right hand side.
Column I Column II
(A) (P) 36%
(B) (Q) 63.8%
(C) (R) 99.9%
(D) (S) 0.2%
Q.11 Match the column:

Column I Column II
(Carbohydrate) (Properties)
(A) Starch (P) Mutarotation
(B) Sucrose (Q) Non reducing sugar
(C) Lactose (R) β-glycosidic bond
(D) Maltose (S) α-glycosidic bond
(T) Reducing sugar
(U) Hemiacetal
APNI KAKSHA 56
Column I Column II
(A) (P) α-glycoside bonds
(B) (Q) Reducing sugar
(C) (R) Forms enediol intermediate
(D) (S) β-glycoside bond

Column I Column II
(Functional group) (Test used or complex formed during confirmatory test)
(A) Aldehydic (P) [(C6 H5 O)6 Fe]−3 (violet)
(B) Phenolic (Q)
(C) Alcohol (R)
(D) α-D- Glucopyranose (S) (ROH)2 Ce(NO3 )4 (Red)

(T) Molisch's Test
APNI KAKSHA 57
Column I Column II
(A) Addition polymer (P) Buna-S
(B) Condensation polymer (Q) Buna-N
(C) Homopolymer (R) Polythene
(D) Copolymers (S) Nylon 6,6
Presence of the element in Complex formed in one Colour of the complex
Na – extract of the test
(A) N (P) Na4 [Fe(CN)5 NOS] (W) Prussian Blue
(B) S (Q) Fe(CNS)3 (X) Black
(C) N and S together (R) PbS (Y) Violet
(S) Fe4 [Fe(CN)6 ] (Z) Blood Red
Subjective Type:
Q.16 The pKa values for the three acidic group P, Q, R are 4.3,9.7 and 2.2 respectively
Calculate the isoelectric point of the amino acid?

Q.17 How will you separate?
(a) Ethane & Ethyne (b) 1-Butyne & 2-Butyne (c) Phenol & Propanol
(d) 2-Propanol & Propanone (e) CH3 COOH&HCOOCH3 (f) PhOH&PhCOOH
(g) C2 H4 &C2 H2 (h) EtNH2 &Me2 NH (i) EtOH&Et − O − Et
Q.18 How will you differentiate?
(a) Propane & Propene (b) 1,1-Dichloroethane & 1,2-Dichloroethane
(c) Chloroethane & Chloroethene (d) Pure & Oxidized CHCl3
(e) p-chlorotoluene & benzylchloride (f) n-propylchloride & isopropylchloride
(g) Methanol & ethanol (h) Isobutanol & tert-butanol
(i) 2-Pentanol & 3-pentanol (j) O-cresol & benzylalcohol
(k) Ethanol & Propanol (l) Propanone & Ethanol
(m) HCHO&PhCHO (n) Glucose & Fructose
(o) HCOOH&CH3 COOH (p) HCOOH&HCHO
(q) MeNH2 &Me2 NH (R)
APNI KAKSHA 58
Q.19 (a) What is the structure of nylon-6, made by alkaline polymerisation of caprolactum.
(b) Suggest mechanism for the process. Is polymerisation of the chain reaction or step reaction
type.
Q.20 Compound (A) C5 H10 O5 give a tetra-acetate with Ac2 O & oxidation of A with Br2 /H2 O gives an
acid C5 H10 O6 . Reduction of A with HI&RedP. Give 2-methyl butane. What is structure of ' A '
Q.21 (i) Sulphanilic acid although has acidic as well as basic group. It is soluble in alkali but insoluble
in mineral acid. Explain.
(ii) Explain why sulphonic acid is not soluble in organic solvents.
Q.22 Account for the fact that 2-amino ethanoic acid (glucine) exist as a dipolar ion as does p-
aminobenzene sulphonic acid but p-amino benzoic acid does not.
Q.23 For given compound
(a) Which glycosidic linkage is present (b) Name of the compound

(c) Products obtained on hydrolysis (d) Is it reducing sugar
(e) Number of moles of HIO4 consumed (f) Is mutarotation possible
(g) Number of moles of CH3 COCl consumed per mole of compound.
Q.24 For given compound
(i) Number of possible isomers

(ii) Number of possible D-configuration isomers
(iii) Number of possible L-configuration isomers
APNI KAKSHA 59
Q.25 Number of possible isomers of α-D-gluco pyronose configuration.
Q.26 Calculate isoelectric point of following amino acid
APNI KAKSHA 60
EXERCISE # IV (JEE-MAIN)
Q.1 Which of the following pairs give positive Tollen's test? [JEE-Main-2004]
(1) Glucose, sucrose (2) Glucose, fructose
(3) Hexanal, Acetophenone (4) Fructose, sucrose
Q.2 Two forms of D-glucopyranose, are called. [JEE-Main-2005]
(1) Enantiomers (2) Anomers (3) Epimers (4) Diastereomers
Q.3 When benzene sulfonic acid and p-nitrophenol are treated with NaHCO3 , the gases released
respectively are [JEE-Main-2006]
(1) SO2 , NO2 (2) SO2 , NO (3) SO2 , CO2 (4) CO2 , CO2
Q.4 Statement-1 : Glucose gives a reddish-brown precipitate with Fehling's solution. because
[JEE-Main-2007]
Statement-2 : Reaction of glucose with Fehling's solution gives CuO and gluconic acid.
(1) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(2) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(3) Statement-1 is True, Statement-2 is False.
(4) Statement-1 is False, Statement-2 is True.
Q.5 Which one of the following bases is not present in DNA ? [JEE-Main-2014]
(1) Cytosine (2) Thymine (3) Quinoline (4) Adenine
Q.6 Which one is classified as a condensation polymer? [JEE-Main- 2014]
(1) Teflon (2) Acrylonitrile (3) Dacron (4) Neoprene
Q.7 Which of the vitamins given below is water soluble? [JEE-Main- 2015]
(1) Vitamin E (2) Vitamin K (3) Vitamin C (4) Vitamin D
Q.8 Which of the following compounds is not an antacid? [JEE-Main- 2015]
(1) Phenelzine (2) Ranitidine
(3) Aluminium hydroxide (4) Cimetidine
Q.9 is used as: [JEE-Main-2015]
(1) Insecticide (2) Antacid (3) Antihistamine (4) Analgesic

Q.10 Thiol group is present in : [JEE-Main-2016]
(1) Methionine (2) Cytosine (3) Cystine (4) Cysteine
Q.11 The distillation technique most suited for separating glycerol from spent-lye in the soap industry
is [JEE-Main-2016]
(1) Distillation under reduced pressure (2) Simple distillation
(3) Fractional distillation (4) Steam distillation
APNI KAKSHA 61
Q.12 Which of the following statements about low density polythene is FALSE? [JEE-Main-2016]
(1) It is used in the manufacture of buckets, dust-bins etc
(2) Its synthesis requires high pressure
(3) It is a poor conductor of electricity
(4) Its synthesis requires dioxygen or a peroxide initiator as a catalyst.
Q.13 Which of the following is an anionic detergent? [JEE-Main-2016]
(1) Glyceryl oleate (2) Sodium stearate
(3) Sodium lauryl sulphate (4) Cetyltrimethyl ammonium bromide
Q.14 The formation of which of the following polymers involves hydrolysis reaction?
[JEE-Main-2017]
(1) Nylon 6 (2) Bakelite (3) Nylon 6,6 (4) Terylenes
Q.15 Which of the following compounds will behave as a reducing sugar in an aqueous KOH solution?
[JEE-Main-2017]
(A) (B)
(C) (D)
Q.16 Glucose on prolonged heating with HI gives : [JEE-Main-2018]

(1) 6-iodohexanal (2) n-Hexane (3) 1-Hexene (4) Hexanoic acid
Q.17 The increasing order of pKa of the following amino acids in aqueous solution is : Gly Asp Lys Arg
[JEE-MAIN2019]
(1) Asp < Gly < Arg < Lys (2) Arg < Lys < Gly < Asp
(3) Gly < Asp < Arg < Lys (4) Asp < Gly < Lys < Arg
Q.18 The correct sequence of amino acids present in the tripeptide given below is :
[JEE MAIN-2019]
(1) Val - Ser – Thr (2) Leu - Ser – Thr (3) Thr - Ser- Leu (4) Thr - Ser – Val
APNI KAKSHA 62
Q.19 The correct structure of product ' P ' in the following reaction is : [JEE MAIN-2019]
(A)
(B)
(C)
(D)
20. Among the following compound which one is found in RNA ? [JEE MAIN-2019]
(A) (B) (C) (D)
21. The correct match between Item I and Item II is :-

[JEE MAIN-2019]
Item I Item II
(A) Ester test (P) Tyr
(B) Carbylamine test (Q) Asp
(C) Phthalein dye test (R) Ser
(S) Lys
APNI KAKSHA 63
(1) (A)→(R); (B)→(S); (C)→(Q) (2) (A)→(R); (B)→(Q); (C)→(P)
(3) (A)→(Q); (B)→(S); (C)→(R) (4) (A)→(Q); (B)→(S); (C)→(P)
22. Among the following compounds most basic amino acid is : [JEE MAIN-2019]
(1) Lysine (2) Asparagine (3) Serine (4) Histidine
23. The correct structure of histidine in a strongly acidic solution (pH = 2) is [JEE MAIN-2019]
(1) (2)
(3) (4)
24. Amylopection is composed of : [JEE MAIN-2019]

(1) α-D-glucose, C1 − C2 and C1 − C6 linkages
(2) β-D-glucose, C1 − C4 and C1 − C6 linkages
(3) β-D-glucose, C1 − C4 and C2 − C6 linkages
(4) α-D-glucose, C1 − C4 and C2 − C6 linkages
25. Number of stereo centers present in linear and cyclic structures of glucose are respectively :
[JEE MAIN-2019]
(1) 4 & 4 (2) 4 & 5 (3) 5 & 5 (4) 5 & 4
26. Glucose and Galactose are having identical configuration in all the positions except position.
(1) C − 5 (2) C − 3 (3) C − 2 (4) C − 4
27. Which of the following statements is not true about RNA? [JEE MAIN-2019]
(1) It has always double stranded α-helix structure
(2) It usually does not replicate
(3) It is present in the nucleus of the cell
(4) It controls the synthesis of protein
28. Which of the given statements is INCORRECT about glycogen? [JEE MAIN-2019]
(1) Only α-linkages are present in the molecule.
(2) It is present in animal cells.
(3) It is present in some yeast and fungi.
(4) It is a straight chain polymer similar to amylose.
APNI KAKSHA 64
29. Maltose on treatment with dilute HCl gives : [JEE MAIN-2019]
(1) D-Glucose (2) D-Fructose
(3) D-Glucose and D-Fructose (4) D-Galactose
30. The major product in the following reaction is : [JEE MAIN-2019]
(1) (2) (3) (4)
31. Fructose and glucose can be distinguished by : [JEE MAIN-2019]

(1) Fehling's test (2) Benedict's test (3) Seliwanoff's test (4) Barfoed's test
32. Which of the following statements is not true about sucrose ? [JEE MAIN-2019]
(1) It is also named as invert sugar
(2) On hydrolysis, it produces glucose and fructose
(3) The glycosidic linkage is present between C1 of α-glucose and C1 of β-fructose
(4) It is a non reducing sugar
33. The peptide that gives positive ceric ammonium nitrate and carbylamine tests is :
[JEE MAIN-2019]
(1) Asp-Gln (2) Ser-Lys (3) Lys-Asp (4) Gln-Asp
34. The correct sequence of amino acids presents in the [JEE MAIN-2019]
(1) Val - Ser - Thr (2) Thr - Ser - Val (3) Leu - Ser - Val (4) Thr - Ser – Leu
35. The inereasing order of pKa of the following amino acids in aqueous solution is:
[JEE MAIN-2019]
Gly Asp Lys Arg
(1) Asp < Gly < Arg < Lys (2) Gly < Asp < Arg < Lys
(3) Asp < Gly < Lys < Arg (4) Arg < Lys < Gly < Asp
APNI KAKSHA 65
36. The correct structure of product ' P ' in the following reaglion is: [JEE MAIN-2019]
Asn − ser + ( CH3CO )2 O ⎯⎯→

NEt 3
P
( excess )
(1) (2)
(3) (4)
37. The correct match between Item I and Item II is: [JEE MAIN-2019]
Item I Item II
(I) Ester test (P) Tyr
(II) Carbylamine test (Q) AsP
(III) Phthalein dye test (R) Ser
(S) Lys
(1) (I) → (Q, R); (II) → (S); (III) → (P) (2) (I) → (R); (II) → (Q); (III) → (P)
(3) (I) → (R); (II) → (S); (III) → (Q) (4) (I) → (Q); (IV) → (S); (III) → (R)
38. fonsider the following rections: [JEE MAIN-2020]
dry HCI x eq. of
(i) Glucose +ROH → Acetal (CH acetyl derivative
3 CO)2 O
Ni/H2 y eq. of
(ii) Glucose → A (CH acetyl derivative
3 CO)2 O
z eq. of
(iii) Glucose (CH acetyl derivative
3 CO)2 O
' x ', ' y ' and ' z ' in these reactions are respectively.
(A) 4,5&5 (B) 4,6&5 (C) 5,4&5 (D) 5,6&5
39. The correct observation in the following reactions is [JEE MAIN-2020]
(A) Gives no colour (B) Formation of red colour

(C) Formation of violet colour (D) Formation of blue colour
APNI KAKSHA 66
40. Which one of the following statements is not true? [JEE MAIN-2020]
(A) Lactose contains α-glycosidic linkage between C1 of galactose and C4 of glucose
(B) Lactose is a reducing sugar and it gives Fehling's test
(C) On acid hydrolysis, lactose gives one molecule of D(+) -glucose and one molecule of
D(+) galactose
(D) Lactose (C11 H22 O11 ) is a disaccharide and it contains 8 hydroxyl groups
41. A, B and C are three biomolecules. The results of the tests performed on them are given below:
A, B and C are respectively: [JEE MAIN-2020]
Molisch's's Test Barfored Test Biuret Test
A Positive Negative Negative
B Positive Positive Negative
C Negative Negative Positive
(A) A = Lactose, B = Glucose, C = Alanine (B) A = Glucose, B = Fructose, C = Albumin
(C) A = Lactose, B = Glucose, C = Albumin (D) A = Lactose, B = Fructose, C = Alanine
42. A peptide synthesized by the regetions of one molecule each of Glycine, Leucine, Aspartic
acid and Histidine will have _____ peptide linkages. [JEE MAIN-2021]
43. Hydrolysis of sucrose gives : [JEE MAIN-2021]
(1) α-D-(-)-Glucose and β-D- (-)-Fructose
(2) α-D-(+)-Glucose and α − D − (−)-Fructose
(3) α-D-(-)-Glucose and α-D-(+)-Fructose
(4) α-D-(+)-Glucose and β − D − (−)-Fructose
44. The warter soluble protein is [JEE MAIN-2021]
(1) Fibrin (2) Albumin (3) Myosin (4) Collagen
45. Which one of the lollowing is correct structure for cytosine? [JEE MAIN-2021]
(1) (2) (3) (4)
46. Match List I with List II. [JEE MAIN-2022]

List-I List -II
Enzyme Conversion of
P. Invertase I. Starch into maltose
Q. Zymase II. Maltose into glucose
R. Diastase III. Glucose into ethanol
S. Maltase IV. Cane sugar into glucose
Choose the most appropriate answer from the options given below :
(1) P-III, Q-IV. R-II. S-I (2) P-III. Q-II. R-I. S-IV
(3) P-IV, Q-IIL R-I. S-II (4) P-IV, Q-II. R-III. S-I
APNI KAKSHA 67
47. Given below are two statements. [JEE MAIN-2022]
Statements I: Maltose has two α-D-glucose units linked at C1 and C4 and is a reducing sugar.
Statement II: Maltose has two monesaccharides: α-D-glucose and β-D-glucose linked at C1 and
C6 and it is a non-reducing sugar.
In the light of the above statements, choose the correct answer from the options given
below.
(A) Both Statement I and Statement II are true
(B) Both Statement I and Statement II are false
(C) Statement I is true but Statement II is false
(D) Statement I is false but Statement II is true
48. Stability of α-Helix structure ofproteins depends upon [JEE MAIN-2022]
(A) dipolar interaction (B) H-bonding interaction
(C) van der Waals forces (D) π-stacking interaction
49. C6H12O6 ⎯⎯⎯
Zymase
→ A ⎯⎯→
NaOl

B + CHI3
The number of carbon atoms present in the product B is [JEE MAIN-2022]

50. Uracil is base present in RNA with the following structure. % of N in uracil is
Given:
Molar mass N = 14 g mol−1 ; O = 16 g mol−1 ; C = 12 g mol−1 ; H = 1 g mol−1; [JEE MAIN-2023]
APNI KAKSHA 68
EXERCISE # V (A) (JEE-ADVANCE) (OBJECTIVE)
Q.1 Statement-1 : p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid.
Because [JEE 2007]
Statement-2 : o-Hydroxybenzoic acid has intramolecular hydrogen bonding.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1.
(D) Statement-1 is False, Statement-2 is True.
Q.2 Match the chemical substances in Column I with type of polymers / type of bonds in Column II.
Indicate your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the
ORS. [JEE 2007]
Column I Column II
(A) Cellulose (P) Natural polymer
(B) Nylon-6, 6 (Q) Synthetic polymer
(C) Protein (R) amide linkage
(D) Sucrose (S) Glycoside linkage
Q.3 Match the compounds/ion in column I with their properties/ reaction in Column II. Indicate
your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS.
[JEE 2007]
Column I Column II
(A) C6 H5 CHO (P) gives precipitate with 2,4-
dinitrophenylhydrazine
(B) CH3 C ≡ CH (Q) gives precipitate with AgNO3
(C) CN − (R) is a nucleophile
(D) I −
(S) is involved in cyanohydrin formation
Q.4 Cellulose upon acetylation with excess acetic anhydride / H2SO4 (catalytic) gives cellulose
triacetate whose structure is [JEE 2008]
(A) (B)
(C) (D)
APNI KAKSHA 69
Q.5 Match the compounds in Column I with their characteristic test(s)/reaction(s) given in Column
II. Indicate your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the
ORS. [JEE 2008]
Column-I Column II
⊕ ⊖
(A) H2 N − NH3 Cl (P) Sodium fusion extract of the compound
gives Prussian blue colour with FeSO4
(B) (Q) Gives positive FeCl3 test
(C) (R) Gives white precipitate with AgNO3
(D) (S) Reacts with aldehydes to form the
corresponding Hydrazone derivative

Q.6 The correct statement(s) about the following sugars X and Y is(are) [JEE 2009]
(A) X is a reducing sugar and Y is a non-reducing sugar

(B) X is a non-reducing sugar and Y is a reducing sugar
(C) The glucosidic linkages in X and Y are α and β, respectively.
(D) The glucosidic linkages in X and Y are β and α, respectively
Q.7 Among cellulose, poly (vinyl chloride), nylon and natural rubber, the polymer in which the
intermolecular force of attraction is weakest is [JEE 2009]
(A) Nylon (B) Poly (vinyl chloride)
(C) Cellulose (D) Natural Rubber
Q.8 The following carbohydrate is [JEE 2011]
(A) a ketohexose (B) an aldohexose (C) an α-furanose (D) an α-pyranose

APNI KAKSHA 70
Q.9 The major product of the following reaction is
(A) a hemiacetal (B) an acetal (C) an ether (D) an ester

Q.10 Amongst the compounds given, the one that would form a brilliant coloured dye on treatment
with NaNO2 in dil. HCl followed by addition to an alkaline solution of β-naphthol is–[JEE 2011]
(A) (B) (C) (D)
Q.11 The correct functional group X and the reagent/reaction conditions Y in the following scheme
are [JEE 2011]
(A) X = COOCH3 , Y = H2 /Ni/ heat (B) X = CONH2 , Y = H2 /Ni/ heat

(C) X = CONH2 , Y = Br2 /NaOH (D) X = CN, Y = H2 /Ni/ heat
Q.12 The structure of D-(+)-glucose is [IIT 2011]
The structure of L(−)-glucose is
(A) (B) (C) (D)
Q.13 For 'invert sugar', the correct statement(s) is (are) : [JEE 2016]
(Given : specific rotations of (+)-sucrose, (+)-maltose, L-(-)-glucose and L-(+)-fructose in
aqueous solution are +66∘ , +140∘ , −52∘ and +92∘ , respectively)
(A) 'invert sugar' is prepared by acid catalyzed hydrolysis of maltose
(B) 'invert sugar' is an equimolar mixture of D − (+) glucose and D − (−)-fructose
(C) specific rotation of 'invert surgar' is −20∘
(D) on reaction with Br2 water, 'invert sugar' forms saccharic acid as one of the products
APNI KAKSHA 71
Comprehension : Q.No. 14 to 15
Treatment of compound O with KMnO4 /H + gave P, which on heating with ammonia
gave Q . The compound Q on treatment with Br2 /NaOH produced R . On strong
heating, Q gave S, which on further treatmenet with ethyl 2-bromopropanoate in the
presence of KOH following by acidification, gave a compound T.
Q.14 The compound R is: [JEE 2016]
(A) (B) (C) (D)
Q.15 The compound 𝐓 is: [JEE 2016]

(A) Glycine (B) Alanine (C) Valine (D) Serine
Q.16 The Fischer presentation of D-glucose is given below. [JEE 2018]
The correct structure(s) of β-L-glucopyranose is (are)
(A) (B) (C) (D)
17. Which of the following statement(s) is(are) true? [JEE 2019]

(A) The two six-membered cyclic hemiacetal forms of D − (+)-glucose are called anomers
(B) Monosaccharides cannot be hydrolysed to give polyhydroxy aldehydes and ketones
(C) Oxidation of glucose with bromine water gives glutamic acid
(D) Hydrolysis of sucrose gives dextrorotatory glucose and laevorotatory fructose
18. Given: [JEE-2021]
APNI KAKSHA 72
The compound(s), which on reaction with HNO3 will give the product having a degree of
rotation, [α]D = –52.7º is(are);
(A) (B) (C) (D)
19. Treatment of D-glucose with aqueous NaOH resuts in a mixture of monosaccharides, which are
[JEE- 2022]
(A)
(B)
(C)
(D)
20. In the given reaction scheme, 𝐏 is a phenyl alkyl ether, 𝐐 is an aromatic compound; 𝐑 and 𝐒 are
the major products. [JEE-2023]
( i) NaOH
(ii)CO2 ( i )(CH CO) O
P ⎯⎯
→Q ⎯⎯⎯→R ⎯⎯⎯⎯→
Hl 3
( iii ) H3O+
( ii )H O+
2
S
3
The correct statement about 𝐒 is

(A) It primarily inhibits noradrenaline degrading enzymes.
(B) It inhibits the synthesis of prostaglandin.
(C) It is a narcotic drug.
(D) It is ortho-acetyl benzoic acid.
APNI KAKSHA 73
EXERCISE # V (B) (JEE-ADVANCE) (SUBJECTIVE)
Q.1 Give the structures of the products in each of the following reactions. [JEE 2000]
+
(i) Sucrose ⎯⎯
H
→A + B (ii)
Q.2 Aspartame, an artifical sweetener, is a peptide and has the following structure: [JEE 2001]
(i) Identify the four functional groups.

(ii) Write the zwitterionic structure.
(iii) Write the structures of the amino acids obtained from the hydrolysis of aspartame.
(iv) Which of the two amino acids is more hydrophobic?
Q.3 Following two amino acids lysine and glutamine form dipeptide linkage. What are two possible
dipeptides? [JEE 2003]
Q.4 The structure of D-Glucose is as follows- [JEE 2004]

(a) Draw the structure of L-Glucose
(b) Give the reaction of L - Glucose with Tollens reagent.
Q.5 Monomer A of a polymer on ozonolysis yields two moles of HCHO and one mole of CH3 COCHO.
[JEE 2005]
(a) Deduce the structure of A.
(b) Write the structure of "all cis" - form of polymer of compound A.
Q.6 A decapeptide (Mol. Wt. 796) on complete hydrolysis gives glycine (Mol. Wt. 75), alanine and
phenylalanine. Glycine contributes 47.0% to the total weight of the hydrolysed products. The
number of glycine units present in the decapeptide is [JEE 2011]
APNI KAKSHA 74
Q.7 The substitutes R1 and R 2 for nine peptides are listed in the table given below. How many of
these peptides are positively charged at pH = 7.0 ? [JEE 2012]
Peptide 𝐑1 𝐑2
I H H
II H CH3
III CH2 COOH H
IV CH2 CONH (CH2 )4 NH2
V CH2 CONH2 CH2 CONH2
VI (CH2 )4 NH2 (CH2 )4 NH2
VII CH2 COOH CH2 CONH2
VIII CH2 OH (CH2 )4 NH2
IX (CH2 )4 NH2 CH3
Q.8 When the following aldohexose exists in its d-configuration, the total number of stereoisomers
in its pyranose form is – [JEE 2012]
Q.9 A tetrapeptide has −COOH group on alanine. This produces glycine (Gly), valine (Val), phenyl
alanine (Phe) and alanine (Ala), on complete hydrolysis. For this tetrapeptide, the number of
possible sequences (Primary structures) with −NH2 group attached to a chiral center is
[JEE 2013]
Q.10. The total number of lone-pairs of electrons in melamine is: [JEE 2013]
Q.11 The total number of distinct naturally occurring amino acids obtained by complete acidic
hydrolysis of the peptide shown below is [JEE 2014]
APNI KAKSHA 75
Q.12 A disaccharide 𝐗 cannot be oxidised by bromine water. The acid hydrolysis of 𝐗 leads to a
laevorotatory solution. The disaccharide 𝐗 is [JEE ADV. 2023]
(A)
(B)
(C)
(D)
APNI KAKSHA 76
ANSWER KEY
EXERCISE-I
1. C 2. D 3. C 4. B 5. C 6. A 7. C
8. D 9. C 10. B 11. B 12. C 13. C 14. A
15. A 16. D 17. D 18. D 19. B 20. B 21. D
22. B 23. A 24. A 25. C 26. A 27. D 28. B
29. B 30. C 31. C 32. C 33. D 34. C 35. A
36. D 37. B 38. C 39. A 40. A 41. B 42. B
EXERCISE-II
1. ABCD 2. ABD 3. ABC 4. ABD 5. ABD 6. ABC 7. BC
8. ABCD 9. ABC 10. BD 11. D 12. A 13. D 14. B
15. C
16. (A)→ PQS; (B)→S; (C)→RS; (D)→QRS;
17. (A)→R; (B)→P; (C)→; (D)→Q;
EXERCISE-III
1. A 2. A 3. A 4. A 5. D 6. B 7. C
8. A 9. C
10. (A)→S; (B)→Q; (C)→P; (D)→R;
11. (A)→QS; (B)→QRS; (C)→PRTU; (D)→PSTU;
12. (A)→PQR; (B)→P; (C)→PS ; (D)→PQR;
13. (A)→QR; (B)→P; (C)→S; (D)→T;
14. (A)→PQR; (B)→S; (C)→R; (D)→PQS;
15. (A)→S-W; (B)→P-Y; R-X (C)→Q-Z
16. 3.25
1. 2 2. 2 3. 4 4. 3 5. 3 6. 3 7. 3
8. 1 9. 4 10. 4 11. 1 12. 1 13. 3 14. 1
15. 1 16. 2 17. 4 18. 1 19. 1 20. 3 21. 4
22. 4 23. 4 24. 4 25. 2 26. 4 27. 1 28. 4
29. 1 30. Bonus 31. 3 32. 3 33. 2 34. C 35. A
36. B 37. A 38. D 39. B 40. A 41. C 42. 3
43. D 44. B 45. C 46. C 47. C 48. B 49. 1
50. 25
EXERCISE # V(A) (JEE-ADVANCE) OBJECTIVE
1. D
2. (A)→PS; (B)→QR; (C)→PR; (D)→S;
3. (A)→PS; (B)→Q; (C)→QRS; (D)→QR;
4. A
5. (A)→RS; (B)→PQ; (C)→PQR; (D)→PS
6. BC
7. D 8. B 9. B 10. C 11. ABCD 12. A 13. BC
14. A 15. B 16. D 17. AD 18. C,D 19. C 20. B
APNI KAKSHA 77
18.
The enantiomer of (P) will have –52.7º rotation. So the reactant must be an isomer of D-
glucose which can given the mirror image of (P)
19.
APNI KAKSHA 78
EXERCISE # V(B) (JEE-ADVANCE) SUBJECTIVE
Q.2 (i) Amine, carboxylic acid, Amide, Ester
Q.4
Q.5
Q.6 6 Q.7 4 Q.8 8 Q.9 4 Q.10 6 Q.11 1 Q.12 (A)
APNI KAKSHA 79
SOLUTION
34. Structure of the given α-amino acids are:
Here, aspartic acid is an acidic and glycine is a neutral amino acid while lysine and arginine are
basic amino acids. Also, arginine is more basic due to the stronger basic functional groups.
∴ The order of pKa value is directly proportional to the basic strength of amino acids, i.e. Arg >
Lys > Gly > Asp.
35.
36.
37.
Name Abrevation Functional group Test
(P) Tyrosine Tyr Phthalein dye test (C)
(Q) Aspartic acid Asp (–CH2COOH) Ester test (A)

(R) Serine Ser (–CH2OH) Ester test (A)
(S) Lysine Lys (–(CH2)4–NH2) Carbylamine test (B)
APNI KAKSHA 80
38. 5 eq. of (CH3 CO)2 O is used in (i) reaction. 6 eq. of (CH3 CO)2 O is used in (ii) reaction
5 eq. of (CH3 CO)2 O is used in (iii) reaction
39.
Ketose with seliwanoff's reagent gives red colour. It is a specific test for ketose.
40. Lactose contains β-glycosidic linkage between C1 of galactose and C4 of glucose.
41.
Lab tests Molisch's test Barfoed test Biuret test
Given by Lactose, Glucose, Fructose Glucose Albumin
Do not given by Fructose Alanine

42.
APNI KAKSHA 81
43. Sucrose is formed by α − D(+). Glucose +β − D(−) Fructose. we obtain these monomers on
hydrolysis.
44. Albumin is water soluble.
45. The correct structure of cytosine
46. Invertase: Cane sugar → Glucose and fructose

Zymase: Glucose → Ethanol and CO2
Diastase: Starch → Maltose
Maltase: Maltose → Glucose
47.
48. Mostly H-bonding is responsible for the stability of α-helix form.
49.
50. Mol. Wt of C4 N2 H4 O2 = 112

28
% N = 112 × 100 = 25%
APNI KAKSHA 82
(Organic Chemistry) POLYMERS & POC
EXERCISE # O-I
1. Which of the following is monomer unit of polystyrene :-
(A) (B) CF2 = CF2 (C) (D)
2. Weakest intermolecular forces are present in :-

(A) Neoprene (B) Terylene (C) Polystyrene (D) Bakelite
3. Thermosetting polymer, Bakelite is formed by the reaction of phenol with :-
(A) CH3 CH2 CHO (B) CH3 CHO (C) HCHO (D) HCOOH
4. Which one is classified as a condensation polymer?
(A) Teflon (B) Acrylonitrile (C) Dacron (D) Neoprene
5. Novolac is a :
(A) linear polymer of urea and formaldehyde
(B) crosslink polymer of urea and formaldehyde
(C) linear polymer of phenol and formaldehyde
(D) crosslink polymer of phenol and formaldehyde
6. Which of the following is not a semisynthetic polymer.

(A) cis-polyisoprene (B) cellulose nitrate (C) cellulose acetate (D) vulcanised rubber
7. Which one of the following polymers is prepared by condensation polymerization

(A) Styrene (B) Nylon-6,6 (C) Teflon (D) Rubber
8. Which of the following statement is not true :
(A) Natural rubber has the trans-configuration at every double bond.
(B) Buna-S is a copolymer of butadiene and styrene.
(C) Natural rubber is a 1, 4-polymer of isoprene.
(D) In vulcanization, the formation of sulphur bridges between different chains make rubber harder and
stronger.
9. Structures of some common polymers are given. Which one is not correctly presented ?
(A) Nylon 66 [ NH (CH2 )6 NHCO (CH2 )4 − CO−]n
(B) Teflon( CF2 − CF2 −)n
(C)
(D)
10. Of the following which one is classified as polyester polymer ?

(A) Terylene (B) Bakelite
(C) Malamine formaldehyde (D) Nylon-66
APNI KAKSHA 61
11. Which one of the following is not a condensation polymer?
(A) Dacron (B) Neoprene (C) Melamineformaldehyde (D) Glyptal
12. Which of the following statements is false?

(A) The repeat unit in natural rubber is isoprene
(B) Both starch and cellulose are polymers of glucose
(C) Artificial silk is derived from cellulose
(D) Nylon-66 is an example of elastomer
13. Which one of the following sets forms the biodegradable polymer ?
(A)
(B)
(C) CH2 = CH − CN and CH2 = CH − CH = CH2

(D) H2 N − CH2 − COOH and H2 N − (CH2 )5 − COOH
14. Nylon is an example of :-

(A) Polythene (B) Polyester (C) Polysaccharide (D) Polyamide
APNI KAKSHA 62
EXERCISE # O-II
1. For the Separation of two immiscible liquids which method (or apparatus) is used?
(1) Chromatography (2) Fractionating column
(3) Fractional distillation (4) Separating funnel / Decantation
2. A mixture of benzene and chloroform is separated by
(1) Sublimation (2) Separating funnel
(3) Crystallization (4) Distillation
3. Which of the following has molecular weight of 92 ?
(1) Toluene (2) Benzene (3) Methanol (4) Propene
4. Aniline is usually purified by
(1) Chromatographic technique (2) Steam distillation
(3) By addition of oxalic acid (4) Fractional crystallization
5. The most suitable method for separation of 1:1 mixture of ortho- and para- nitrophenols is
(1) Sublimation (2) Chromatography (3) Crystallization (4) Steam distillation
6. Distillation under reduced pressure is employed for
(1) Benzene (2) Petrol
(3) Glycerol (4) Organic compounds used in medicine
7. Impure glycerine is purified by
(1) Steam distillation (2) Simple distillation
(3) Vacuum distillation (4) None of the above
8. Absolute alcohol is prepared by
(1) Fractional distillation (2) Kolbe's method
(3) Azeotropic distillation (4) Vacuum distillation
9. The latest technique used for purification for organic compuounds in
(1) Chromatography (2) Vacuum distillation
(3) Fractional distillation (4) Crystallisation
10. In paper chromatography
(1) Moving phase is liquid and stationary phase is solid
(2) Moving phase is liquid and stationary phase is liquid
(3) Moving phase is solid and stationary phase is solid
(4) Moving phase is solid and stationary phase is liquid
11. A is a lighter phenol and B is an aromatic carboxylic acid. Separation of mixtue A and B can be
carried out easily by using a solution of
(1) Sodium hydroxide (2) Sodium sulphate
(3) Calcium chloride (4) Sodium bicarbonate
APNI KAKSHA 63
12. In sodium fusion test of organic compounds the nitrogen of the organic compound is converted
into
(1) Sodamide (2) Sodium cyanide (3) Sodium nitrite (4) Sodium nitrate
13. The Lassaigne's extract is boiled with dil. HNO3 before testing for halogens because
(1) Silver halides are soluble in HNO3 (2) Na2 S and NaCN are decomposed by HNO3
(3) Ag 2 S is soluble in HNO3 (4) AgCN is soluble in HNO3
14. In a Lessaigne's test for nitrogen, the blue colour is due to the formation of
(1) Potassium ferricyanide (2) Sodium cyanide
(3) Sodium ferrocyanide (4) Ferri-ferro cyanide
15. Which of the following compounds does not show Lassaigne test for nitrogen?
(1) Urea (2) Hydrazine (3) Phenyl hydrazine(4) Azo benzene
16. When piece of human hair are heated srongly with soda lime smell of ammonia can be detected.
which one of the following conclusion can be drawn from this observation.
(1) Ammonia is present in human hair (2) Ammonium salt is present in hair
(3) Hair contains amino acids (4) None of the above
17. The Beilstein test for organic compounds is used to detect
(1) Nitrogen (2) Sulphur (3) Carbon (4) Halogen
18. Which of the following is the best scientific method to test presence of water in liquid?
(1) Smell (2) Taste
(3) Use of litmus paper (4) Use of anhydrous copper sulphate
19. Liebig's method is used for the estimation of
(1) Nitrogen (2) Sulphur
(3) Carbon and hydrogen (4) Halogens
20. 0.765 gm of an acid gives 0.535 gm of CO2 and 0.138gm of H2 O. Then the ratio of percentage of
carbon and hydrogen is
(1) 19: 2 (2) 18: 11 (3) 20: 17 (4) 1: 7
21. Nitrogen is an organic compound can be estimated by
(1) Kjeldahl's method only (2) Duma's method only
(3) Both the methods (4) none of these methods
22. Dumas method involves the determination of nitrogen content in the organic compound in form
of
(1) NH3 (2) N2 (3) NaCN (4) (NH4 )2 SO4
23. In Kjeldahl's method, nitrogen present is estimated as
(1) N2 (2) NO (3) NH3 (4) NO2
24. The percentage of sulphur in an organic compound whose 0.32 g produces 0.233 g of BaSO4
[At.wt.Ba = 137, S = 32 ] is
(1) 1.0 (2) 10.0 (3) 23.5 (4) 32.1
APNI KAKSHA 64
25. If 0.2 gram of an organic compound containing carbon, hydrogen and oxygen on combustion,
yielded 0.147 gram carbon dioxide and 0.12 gram water. What will be the content of oxygen in
the substance?
(1) 73.29% (2) 78.45% (3) 83.23% (4) 89.50%
26. If a compound on analysis was found to contain C = 18.5%, H = 1.55%, Cl = 55.04% and
Oxygen = 24.81%, Then the empirical formula is
(1) CHClO (2) CH2 ClO (3) C2 H2 OCl (4) ClCH2 O
27. An organic compound contains C = 40%, H = 13.33% and N = 46.6% . Its empirical formula
would be
(1) CHN (2) C2 H2 N (3) CH4 N (4) C3 H7 N
28. Two elements X (atomic weight = 75 ) and Y (atomic weight=16) combine to give a compound
having 75.8%X. The formula of the compound is
(1) XY (2) X2 Y (3) X 2 Y2 (4) X2 Y3
29. On analysis a saturated hydrocarbon is found to contain 83.70% carbon and 16.30% hydrogen.
The empirical formula will be (at wt. of C = 12, at. wt. of H = 1 )
(1) C3 H6 (2) C3 H8 (3) C3 H4 (4) C6 H12
30. Empirical formula of a hydrocarbon containing 80% carbon and 20% hydrogen is
(1) CH (2) CH2 (3) CH3 (4) CH4
31. An organic compound with C = 40% and H = 6.7% will have the empirical formula
(1) CH4 (2) CH2 O (3) C3 H6 O3 (4) C2 H4 O2
32. In a hydrocarbon, mass ratio of hydrogen and carbon 1: 3, the empirical formula of hydrocarbon
is
(1) CH4 (2) CH2 (3) C2 H (4) CH3
33. 8.24 g of a volatile liquid on vaporization gives 45ml of vapours at NTP. What will be the vapour
density of the substance? (Density of H2 = 0.089 g L−1 )
(1) 95.39 (2) 39.95 (3) 99.53 (4) 59.93
34. 0.1914 g of an organic acid is dissolved in about 20ml of water. 25ml of 0.12 N. NaOH is required
for the complete neutralization of the acid solution. The equivalent weight of the acid is
(1) 65.0 (2) 64.0 (3) 63.8 (4) 62.5
35. The equivalent weight of an acid is equal to
(1) Molecular weight x acidity (2) Molecular weight x basicity
(3) Molecular weight/basicity (4) Molecular weight /acidity
36. Simple distillation can be used to separate liquids which differ in their boiling points at least by
(1) 5∘ C (2) 10∘ C (3) 35 − 50∘ C (4) 100∘ C
37. Empirical formula of a compound is CH2 O. If its vapour density is 90, then the molecular formula
of the compound is
(1) C5 H10 O5 (2) C3 H6 O3 (3) C6 H12 O6 (4) C4 H8 O4
APNI KAKSHA 65
38. The empirical formula of an acid is CH2 O2 , the probable molecular formula of the simplest acid
may be
(1) CH2 O (2) CH2 O2 (3) C2 H4 O4 (4) C3 H6 O6
39. A gaseous hydrocarbon has 85% carbon and vapour density of 28 . The possible formula of the
hydrocarbon will be
(1) C3 H6 (2) C2 H4 (3) C2 H2 (4) C4 H8
40. a hydrocarbon has C = 85.72% and remaining H. The hydrocarbon is
(1) C2 H4 (2) C2 H6 (3) C2 H2 (4) CH4
41. An organic compound containing carbon, hydrogen and oxygen contains 52.2% carbon 13.04%
hydrogen. Vapour density of the compound is 23. Its molecular formula will be
(1) C2 H6 O (2) C3 H8 O (3) C4 H8 O (4) C5 H10 O
42. percentage of Se(at.wt 78.4) in peroxidase anhydrase enzyme is 0.5% by weight, then minimum
molecular weight of peroxidase anhydrase enzyme is
(1) 1.568 × 104 (2) 1.568 × 103 (3) 15.68 (4) 2.136 × 104
43. The emprical formula of a compound is CH2 . One of the compound has a mass of 42 g. its
molecular formula is
(1) CH2 (2) C2 H2 (3) C3 H6 (4) C3 H8
44. In a compound C, H and N atoms are present in 9:1:3.5 by weight. If molecular weight of the
compound is 108 , then the molecular formula of the compound is
(1) C2 H6 N2 (2) C3 H4 N (3) C6 H8 N2 (4) C9 H12 N3
45. The following is the percentage composition of a compound. Na = 16.08%, C = 4.19%, O =
16.78%, and H2 O = 62.95%. Its molecular formula is
(1) Na2 CO3 (2) Na2 CO3 H2 O (3) Na2 CO3 ⋅ 10H2 O (4) Na2 CO3 ⋅ 5H2 O
46. An organic compound contains 49.3% carbon, 6.84% hydrogen and its vapour density is 73 .
Empirical Formula of the compound is
(1) C3 H5 O2 (2) CH10 O4 (3) C3 H10 O2 (4) C4 H10 O4
47. Molecular mass of a volatile substance may be obtained by
(1) Kjeldahl's method (2) Duma's method
(3) Victor meyer's method (4) Liebig's method
48. The most suitable method of separation of 1: 1 mixture of ortho and para nitro phenol is
(1) Distillation (2) Crystallization (3) Sublimation (4) Chromatography]
49. Kjeldahl's method can not be used for the estimation of Nitrogen in
(1) Pyridine (2) Nitro compounds(3) Azo compounds (4) All
50. In Kjeldahl's method nitrogen present is estimated as
(1) N2 (2) NH3 (3) NO2 (4) None
APNI KAKSHA 66
EXERCISE # JEE-MAINS & ADVANCED
Q.1 Major product of the following reaction is: [JEE-MAINS 2019]
(1) (2)
(3) (4)
Q.2 The major product of the following reaction is: [JEE-MAINS 2019]
(1) (2)
(3) (4)
Q.3 The major product of the following reaction is: [JEE-MAINS 2019]
(1) (2) (3) (4)
APNI KAKSHA 67
Q.4 The correetmatch between Item - I and Item- II is: [JEE-MAINS 2019]
Item-I Item-II
(a) High density polythene (I) Peroxide catalyst
(b) Polyacrylonitrile (II) Condensation at high temperature/ & pressure
(c) Novolac (III) Ziegler-Natta catalyst
(d) Nylon 6 (IV) Acid or base catalyst
(1) (a) → (IV), (b) → (II), (c) → (I), (d) → (III)

(2) (a) → (II), (b) → (IV), (c) → (I), (d) → (III)
(3) (a) → (III), (b) → (I), (c) → (II), (d) → (IV)
(4) (a) → (III), (b) → (I), (c) → (IV), (d) → (II)
Q.5 Which one of the following polymers is not obtained by condensation polymerisation?
[JEE-MAINS 2020]
(A) Buna-N (B) Nylon 6 (C) Bakelite (D) Nylon 6,6
Q.6 Consider the Assertion and Reason given below. [JEE-MAINS 2020]
Assertion (A): Ethene polymerized in the presence of Ziegler Natta Catalyst athigh
temperature and pressure is used to make buckets and dustbins.
Reason (R) : High density polymers are closely packed and are chemically inert.
Choose the correct answer from the following:
(A) Both (A) and (R) are correct and (R) is the correct explanation of (𝐴).
(B) Both (𝐴) and (𝑅) are correct but (𝑅) is not the correct explanation of (𝐴).
(C) (A) is correct but (R) is wrong
(D) (A) and (R) both are wrong
Q.7 The correct match between Item-I and Item-II is [JEE-MAINS 2020]
Item – I Item - II
(a) Natural rubber (I) 1, 3-butadiene + styrene
(b) Neoprene (II) 1, 3-butadiene + acrylonitrile
(c) Buna- N (III) Chloroprene
(d) Buna-S (IV) Isoprene
(A) (a) −(111), (𝑏) − (𝐼𝑉), (𝑐) − (1), (𝑑) − (11)
(B) (a) - (IV), (b) - (III), (c) - (II), (d) - (1)
(C) (a) - (III), (b) - (IV), (c) - (II), (d) - (1)
(D) (a) − (IV), (b) − (III), (c) − (I), (d) − (II)
APNI KAKSHA 68
Q.8 Preparation of Bakelite proceeds via reactions: [JEE-MAINS 2020]
(A) Electrophilic substitution followed by condensation.
(B) Nucleophilic addition followed by dehydration.
(C) Electrophilic addition followed by dehydration.
(D) Hydration followed by condensation.
Q.9 Match List I with List II [JEE-MAINS 2023]
List-I (Name of polymer) List II (Uses)
A. Glyptal I. Flexible pipes
B. Neoprene II. Synthetic wool
C. Acrilan III. Paints and Lacquers
D. LDP IV. Gaskets
Choose the correct answer from the options given below :-

(1) A-III, B-II, C-IV, D-I (2) A-III, B-IV, C-II, D-I
(3) A-III, B-IV, C-I, D-II (4) A-III, B-I, C-IV, D-II
Q.10 Match List-I and List-II. [JEE-MAINS 2023]
List-I List-II
A. Elastomeric I. Urea formaldehyde

polymer resin
B. Fibre polymer II. Polystyrene
C. Thermosetting
III. Polyester
polymer
D. Thermoplastic
IV. Neoprene
polymer
Choose the correct answer from the options given below:

(1) A-II, B-III, C-I, D-IV (2) A-II, B-I, C-IV, D-III
(3) A-IV, B-III, C-I, D-II (4) A-IV, B-I, C-III, D-II
Q.11 Caprolactam when heated at high temperature in presence of water, gives
[JEE-MAINS 2023]
(1) Teflon (2) Dacron (3) Nylon 6,6 (4) Nylon 6
APNI KAKSHA 69
Q.12 Among the following, the correct statement(s) about polymers is(are) [JEE-Adv. 2022]
(A) The polymerization of chloroprene gives natural rubber.
(B) Teflon is prepared from tetrafluoroethene by heating it with persulphate catalyst at high
pressure.
(C) PVC are thermoplastic polymers.
(D) Ethene at 350-570 K temperature and 1000 - 2000 atm pressure in the presence of a
peroxide initiator yields high density polythene.
Q.13 Consider the following reaction. [JEE-Adv. 2022]
On estimation of bromine in 1.00 g of 𝐑 using Carius method, the amount of AgBr formed (in g )
is [Given: Atomic mass of H = 1, C = 12, O = 16, P = 31, Br = 80, Ag = 108 ]
Q.14 The reaction of 4-methyloct-1-ene (𝐏, 2.52 g) with HBr in the presence of (C6 H5 CO)2 O2 gives
two isomeric bromides in a 9: 1 ratio, with a combined yield of 50% . Of these, the entire
amount of the primary alkyl bromide was reacted with an appropriate amount of diethylamine
followed by treatment with aq. K 2 CO3 to give a non-ionic product 𝐒 in 100% yield.
The mass (in mg ) of 𝐒 obtained is_______.
[Use molar mass (in gmol−1 ) : H = 1, C = 12, N = 14, Br = 80 ] [JEE-Adv. 2023]
APNI KAKSHA 70
ANSWER KEY
EXERCISE # O-I
1. D 2. A 3. C 4. C 5. C 6. A 7. B
8. A 9. C 10. A 11. B 12. D 13. D 14. D
EXERCISE # O-II
1. 4 2. 4 3. 1 4. 2 5. 4 6. 3 7. 3
8. 3 9. 1 10. 2 11. 4 12. 2 13. 2 14. 4
15. 2 16. 3 17. 4 18. 4 19. 3 20. 1 21. 3
22. 2 23. 3 24. 2 25. 1 26. 1 27. 3 28. 4
29. 2 30. 3 31. 2 32. 1 33. 4 34. 3 35. 3
36. 3 37. 3 38. 2 39. 4 40. 1 41. 1 42. 1
43. 3 44. 3 45. 3 46. 1 47. 3 48. 1 49. 4
50. 2

1. (4) 2. (1) 3. (4) 4. (4) 5. (A) 6. (A)
7. (B) 8. (A) 9. (2) 10. (3) 11. (4) 12. (B,C)
13. (1.50) 14. (1791)
APNI KAKSHA 71
SOLUTION
1. Mechanism for the formation of major product is as follows:
2. Reaction involved:
3.
APNI KAKSHA 72
4. a. HDPE - Ziegler-Natta catalyst
b. Polyacrylonitrile - Peroxide catalyst
c. Novolac - Catalysed by acid or base
d. Nylon-6 - Condensation at high T and P
5. Buna- N : Obtained by addition polymerisation Nylon 6 , Bakelite, Nylon 6,6 :
Obtained by condensation polymerisation.
6. High density polyethene is hard and chemically inert thats why used to make buckets
and dustbins.
7. Natural rubber - Polymer of isoprene Neoprene
Polymer of chloroprene Buna N
Polymer of 1,3 -Butadiene and acrylonitrile
Buna S
Polymer of 1,3 -Butadiene and styrene
8. Formation of Bakelite follows electrophilic substitution reaction of phenol with
formaldehyde followed by condensation.
9. Fact based
10. Neoprene : Elastomer
Polyester : Fibre
Polystyrene : Thermoplastic
Urea-Formaldhyde Resin: Thermosetting polymer
11.
APNI KAKSHA 73
12. Polymerization of chloroprene gives synthetic rubbers not natural rubbers. Teflon is prepared
from tetrafluoroethene by heating it with persulphate catalyst at high pressure. PVC are
thermoplastic polymers. High density polythene is formed when addition polymerization of
ethene takes place in a hydrocarbon solvent in the presence of a catalyst such as
triethylaluminium and titanium tetrachloride (Ziegler-Natta catalyst) at a temperature of
333 K to 343 K and under a pressure of 6 − 7 atmospheres.
13.
14.
APNI KAKSHA 74

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(Organic Chemistry) Classification and Nomenclature

Q.10 The correct IUPAC name of the compound

Q.11 The IUPAC name of

Q.12 IUPAC name of is:

(A) But-2-ene-2,3-diol (B)Pent-2-ene-2,3-diol

Q.13 IUPAC name of 𝐂𝐇𝟐 = 𝐂𝐇 − 𝐂𝐍 is:

Q.14 The IUPAC name of

(A) N-Methyl-N-ethyl ethanamine (B) Diethyl methanamine

Q.15 The IUPAC name of acetyl acetone is:

Q17. (a) and (b)

True statement for the above compounds is:

Q.20 The correct IUPAC name of is:

(A) 2-Methyl butanoic acid (B) 2-Ethylprop-2-enoic acid

Q.21 The correct IUPAC name of 2-ethylpent-3-yne is:

Q.22 All the following IUPAC names are correct except:

Q.24 The correct IUPAC name of

(A) 3-Cyclohexanol Propyne

Q.27 The IUPAC name of the compound is:

(A) 4-Pro-1-enyl hepta-1,6-diene (B) 4-Propylidene hepta-1,6-diene

(A) 1,1-Dimethyl-3-hydroxy cyclohexane

(A) 2-Chloro-4-N-ethylpentanoic acid (B) 2-Chloro-3-(N,N-diethyl amino)-propanoic acid

Q.30 The IUPAC name of the compound is

(A) 1-Amino-1-phenyl-2-methyl propane

(B) ; 2-Methyl hex-3-enoic acid

(C) 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐂𝐇 = 𝐂𝐇𝐂𝐎𝐂𝐇𝟑 ; Hex-3-en-2-one

Q.32 The correct IUPAC name of the following compound is:

(A) 3,3-Diformylpropanoic acid

(A) 2-Cyano-3-oxopentanal (B) 2-Formyl-3-oxopentanenitrile

(A) 2, 3-diethyl butane (B) 2-ethyl-3-methyl pentane

Q.35 The IUPAC name of compound is

(A) 3,5-Dimethyl-4-Formyl pentanone (B) 1-Isopropyl-2-methyl-4-oxo butanal

Q.36 The IUPAC name of compound is

(A) 2-Amino-3-chloro-2-methylpent-2-enoic acid

(A) 3-Amino-2-formyl butane-1, 4-dioic acid

(A) N-Formyl aminoethane (B) N-Ethyl formyl amine

Q.39 The IUPAC name of the structure is:

(A) 1,2-Dimethyl-Cyclohexane (B) 1,6-Dimethyl-Cyclohexene

(A) 2-Bromomethyl-3-oxohexanamide (B) 1-Bromo-2-amino-3-oxohexane

(A) 1,2,3-Tricyano propane (B) Propane-1,2,3-trinitrile

Q.43 The IUPAC name of compound

(A) 3-Carbonyl methoxy -5- Ethanoyl oxy cyclohexanic aicd

Q.44 The IUPAC name of is:

(A) 1-Acetoxy acetic acid (B) 2-Acetoxy ethanoic acid

The correct IUPAC systematic name of the above compound is:

Q.46 The IUPAC name of is

(A) 3-Methyl cyclobut-1-ene-2-ol (B) 4-Methyl cyclobut-2-ene-1-ol

Q.47 The IUPAC name of is

(A) 2-Methoxy-4-nitro benzaldehyde (B) 4-Nitro anisaldehyde

(A) 2-(Hydroxy methyl) methyl propanedioate

Q.49 The IUPAC name of

(A) 2-Formyl ethanoic propanoic Anhydride

Q.50 The IUPAC name of

Q.51 The IUPAC name of is:

(A) 2-Chlorocarbonyl ethylbenzoate (B) 2-Carboxyethyl benzoyl chloride

Q.52 The IUPAC name of is:

(A)Phenyl ethenone (B) Methyl phenyl ketone

(A) 1,2,3-Tri hydroxy propane (B) 3-Hydroxy pentane-1,5-diol

Q.6 The group of heterocylic compounds is:

(B) Neopentane (Q)

(C) Ethylidene chloride (R)