RA Sir JEE PYQ Organic Chemistry

CONTENT
JEE CRASH COURCE

S.No Pages
1. Nomenclature of organic compounds 01 – 07
2. Isomerism 8 – 17
3. General Organic Chemistry 18 – 31
4. Hydrocarbon 32 – 53
5. Halogen Derivative 54 – 77
6. Alcohol & Ether 78 – 95
7. Grignard Reagent 96 – 101
8. Oxidation & Reduction of Organic Compound 102 – 103
9. Carbonyl Compound 104 – 136
10. Carboxylic Acid and its derivative 137 – 151
11. Name Reactions 152 –156
12. Phenol & Aniline (Carbene & Nitrene Mechanism based) 157 – 167
13. Practical Organic Chemistry 168 – 169
14. Biomolecules 170 – 181
15. Polymer 182 – 185
16. Chemistry in Everyday Life 186 – 190

ORGANIC CHEMISTRY
NOMENCLATURE OF ORGANIC COMPOUND
[JEE-MAIN / AIEEE]
1. Of the following compounds which has a wrong IUPAC name - [AIEEE-2002]
 CH3 – CH2 – CH2 – C – O – CH2 – CH3
||
O
ethyl butanoate
 CH3 – CH – C – CH – CH3
| || |
CH3 O CH3
2,4- dimethyl -3- pentanone
CH3
|
 H3C – CH – CH – CH3
|
OH
2-methyl -3- butanol
IV CH3 – CH2 – CH2 – CHO
butanal
(A)  (B)  (C)  (D) IV
2. The IUPAC name of CH3COCH(CH3)2 is – [AIEEE-2003]
(A) 4-methylisopropyl ketone (B) 3-methyl-2-butanone
(C) Isopropylmethyl ketone (D) 2-methyl-3-butanone
3. The IUPAC name of the compound [AIEEE-2004]
is -
(A) 3,3 -dimethyl-1-hydroxy cyclohexane (B) 1, 1 – dimethyl–3– hydroxy cyclohexane

(C) 3,3-dimethyl-1-cyclohexanol (D) 1,1 - dimethyl - 3- cyclohexanol
4. The IUPAC name of the compound shown below is - [AIEEE-2006]
(A) 6-bromo-2-chlorocyclohexene (B) 3-bromo-1-chlorocyclohexene

(C) 1-bromo-3-chlorocylohexene (D) 2-bromo-6-chlorocycohex-1-ene
5. The IUPAC name of [AIEEE-2007]
is –
(A) 1, 1-diethyl-2-dimethylpentane (B) 4, 4-dimethyl-5, 5-diethylpentane

(C) 5, 5-diethyl-4, 4-dimethylpentane (D) 3-ethyl-4, 4 dimethylheptane
6. The correct decreasing order of priority for the functional groups of organic compounds in the
IUPAC system of nomenclature is [AIEEE 2008]
(A) –SO3H, –COOH, –CONH 2, –CHO (B) –CHO, –COOH, –SO 3H, –CONH2
(C) –CONH2, –CHO, –SO3H, –COOH (D) –COOH, –SO3H, –CONH2, –CHO
NUCLEUS-92, Rajeev Gandhi Nagar, Kota (Raj.) India 324005, Mob. 9358006181, 97831-97831 1
ORGANIC CHEMISTRY
7. The IUPAC name of neopentane is : [AIEEE -2009]

(A) 2-methylpropane (B) 2, 2-dimethylbutane
(C) 2-methylbutane (D) 2, 2-dimethylpropane
8. The IUPAC name of compound is :- [AIEEE -2012 (Online)]
(A) 1, 2-Epoxy propane (B) Propylene oxide

(C) 1, 2-Oxo propane (D) 1, 2-Propoxide
9. The IUPAC name of the followig compounds is : [AIEEE -2012 (Online)]
(A) (Z) – 5– hepten – 3 – yne (B) (Z) – 2– hepten – 4 – yne

(C) (E) – 5– hepten – 3 – yne (D) (E) – 2– hepten – 4 – yne
10. Aspirin is known as : [AIEEE -2012]

(A) Acetyl salicyclic acid (B) Phenyl salicylate
(C) Acetyl salicylate (D) Methyl salicylic acid
11. The IUPAC name for the following compound is [JEE Main 2019]
CH3
H3C CH
CH3
CH2
(A) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne
(B) 3, 5-dimethyl-4-propylhept-6-en-1-yne
(C) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
(D) 3, 5-dimethyl-4-propylhept1-en-6-yne
12. The correct IUPAC name of the following compound is NO2 [JEE Main 2019]
(A) 2-methyl-5-nitro-1-chlorobenzene
(B) 3-chloro-1-methyl-nitrobenzene
(C) 2-chloro-1-methyl 1-4-nitribenzene
Cl
(D) 5-chloro-4-methyl 1-1-nitrobenzene
CH3
ORGANIC CHEMISTRY
13. Which of the following compounds will show the maximum ‘enol’ content ? [JEE Main 2019]
(A) CH3COCH3 (B) CH3COCH2COCH3
(C) CH3COCH2COOC2H5 (D) CH3COCH2CONH2
14. The IUPAC name of the following compound is [JEE Main 2019]
CH3 OH
H3C CH CH CH2 COOH
(A) 4,4-dimethyl-3-hydroxybutanoic acid (B) 2-methyl-3-hydroxypentan-5-oic acid
(C) 3-hydroxy-4-methylpentanoic acid (D) 4-methyl-3-hydroxypentanoic acid
15. What is the IUPAC name of the following compound ? [JEE Main 2019]
CH3 CH3
H
H
Br
CH3
(A) 3-bromo-3-methyl-1, 2-dimethylprop-1-ene

(B) 3-bromo-1, 2-dimethylbut-1-ene
(C) 2-bromo-3-methylpent-3-ene
(D) 4-bromo-methylpent-2-ene
16. The IUPAC name for the following compound is : [JEE-Main-2020]
(A) 2,5-dimethyl-6-carboxy-hex-3-enal (B) 2,5-dimethyl-5-carboxy-hex-3-enal

(C) 6-formyl-2-methyl-hex-3-enoic (D) 2,5-dimethyl-6-oxo-hex-3-enoic acid
17. The IUPAC name of the following compound is : [JEE-Main-2020]
(A) 3-bromo-5-methylcyclopentane (B) 3-bromo-5-methylcyclopentanoic acid

(C) 5-bromo-5-methylcyclopentanoic acid (D) 4-bromo-2-methylcyclopentanecarboxylic acid
ORGANIC CHEMISTRY
18. The IUPAC name of the following compound is : [JEE-Main-2020]
(1) 2-nitro-4-hydroxymethyl-5 amino benzaldehyde

(2) 3-amino-4-hydroxymethyl-5-nitrogenbenzaldehyde
(3) 4-amino-2-formyl-5-hydroxymethyl nitrogenbenzene
(4) 5-amino-4-hydroxymethyl-2-nitrobenzaldehyde
[JEE-ADVANCED]
1. The IUPAC name of the compound having the formula is:
CH 3
|
H 3C  C  CH  CH 2
|
CH 3
(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 [JEE 1984]
2. Write the IUPAC name of CH3CH2CH = CHCOOH [JEE 1986]
3. The IUPAC name of the compound CH2=CH–CH(CH3)2 is:

(A) 1,1-dimethyl-2-propene (B) 3-methyl-1-butene
(C) 2-vinyl propane (D) None of the above [JEE 1987]
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
5. Write I.U.P.A.C name of following:
(a) Me = methyl group [JEE 1990]
CH 3
|
(b) H 3C  N — CH  CH 2CH 3 [JEE 1991]
| |
CH 3 C 2 H 5
ORGANIC CHEMISTRY
6. Write IUPAC name of succinic acid. [JEE 1994]
7. The IUPAC name of C6H5COCl is

(A) Benzoyl chloride (B) Benzene chloro ketone
(C) Benzene carbonyl chloride (D) Chloro phenyl ketone [JEE 2006]
8. The IUPAC name of the following compound is [JEE 2009]

CN
Br
HO
(A) 4-Bromo-3-cyanophenol (B) 2-Bromo-5-hydroxybenzonitrile
(C) 2-Cyano-4-hydroxybromobenzene (D) 6-Bromo-3-hydroxybenzonitrile
9. The correct structure of ethylenediaminetetraacetic acid (EDTA) is [IIT-JEE 2010]

HOOC–CH 2
CH2–COOH
(A) N–CH=CH–N
HOOC–CH 2 CH2–COOH
HOOC COOH
(B) N–CH2–CH2–N
HOOC COOH
HOOC–CH 2
CH2–COOH
(C) N–CH2–CH 2–N
HOOC–CH 2 CH2–COOH
COOH
HOOC–CH2 CH2
H
N– CH – CH – N
(D) H CH2 CH2–COOH
HOOC
10. The total number of lone-pairs of electrons in melamine is [JEE Advance 2013]
11. The correct combination of names for isomeric alcohols with molecular formula C4H10O is/are
(A) tert-butanol and 2-methylpropan-2-ol
(B) tert-butanol and 1,1-dimethylethan-1-ol
(C) n-butanol and butan-1-ol
(D) isobutyl alcohol and 2-methylpropan-1-ol [JEE Advance 2014]
ORGANIC CHEMISTRY
12. The IUPAC name(s) of the following compound is(are) [JEE Advance 2017]
H3C Cl
(A) 1-chloro-4-methylbenzene (B) 4-chlorotoluene

(C) 1-methyl-4-chlorobenzene (D) 4-methylchlorobenzene
13. Which one of the following structures has the IUPAC name [JEE Advance 2020]
3-ethynyl-2-hydroxy-4-methylhex-3-en-5-ynoic acid ?
(A) (B) (C) (D)
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. C 2. B 3. C 4. B 5. D 6. D 7. D
8. A 9. D 10. A 11. D 12. C 13. B 14. C
15. D 16. D 17. D 18. D
[JEE-ADVANCED]
1. C
2. CH 3  CH 2  CH  CH  COOH
5 4 3 2 1
Pent-2-en-1-oic acid or Pent-2-enoic acid

3. B 4. B
5. (a) 5,6-diethyl-3-methyl-dec-4-ene (b) N,N, 3-trimethyl-3-pentanamine
6. Butane-1,4-dioic acid 7. C 8. B 9. C 10. 6
11. ACD 12. AB 13. D
ORGANIC CHEMISTRY
ISOMERISM
[JEE-MAIN / AIEEE]
Single Choice Questions :
1. A similarity between optical and geometrical isomerism is that [AIEEE-2002]
(A) each forms equal number of isomers for a given compound
(B) If in a compound one is present then so is the other
(C) both are included in stereoisomerism
(D) they have no similarity
2. Which of the following does not show geometrical isomerism ? [AIEEE-2002]

(A) 1, 2-dichloro-1-pentene (B) 1, 3-dichloro-2-pentene
(C) 1, 1-dichloro-1-pentene (D) 1,4-dichloro-2-pentene
3. Racemic mixture is formed by mixing two [AIEEE-2002]

(A) isomeric compounds (B) chiral compounds
(C) meso compounds (D) optical isomers
4. Among the following four structures I to IV [AIEEE-2003]
CH3 O CH3 H CH3

| || | | |
C2H5 — CH — C3H7 CH3 — C — CH — C2H5 H—C C2H5 — CH — C2H5
|
H
(I) (II) (III) (IV)
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
5. On mixing a certain alkane with chlorine and irradiating it with ultraviolet light, it forms only one
monochloroalkane. This alkane could be [AIEEE-2003]
(A) propane (B) pentane (C) isopentane (D) neopentane
6. Which of the following will have meso-isomer also ? [AIEEE-2004]

(A) 2- chlorobutane (B) 2- hydroxy propanoic acid
(C) 2,3 – dichloropentane (D) 2-3- dichlorobutane
7. Amongst the following compound, the optically active alkane having lowest molecular mass is
[AIEEE-2004]
(A) H3C CH3 (B) H3C

CH
CH3 CH3
CH3
(C) H3C (D)

C2H5 H3C CH3
ORGANIC CHEMISTRY
8. Which of the following compound is not chiral ? [AIEEE-2004]
(A) 1- chloropentane (B) 3-chloro-2- methyl pentane
(C) 1-chloro -2- methyl pentane (D) 2- chloropentane
9. Due to the presence of an unpaired electron, free radicals are: [AIEEE-2005]
(A) Chemically reactive (B) Chemically inactive
(C) Anions (D) Cations
10. 2 methylbutane on reacting with bromine in the presence of sunlight gives mainly [AIEEE-2005]
(A) 1 – bromo -2- methylbutane (B) 2–bromo-2-methylbutane
(C) 2 – bromo -3- methylbutane (D) 1–bromo-3-methylbutane
11. Of the five isomeric hexanes, the isomer which can give two monochlorinated compounds is
[AIEEE-2005]
(A) n-hexane (B) 2, 3-dimethylbutane
(C) 2,2-dimethylbutane (D) 2-methylpentane
12. Which types of isomerism is shown by 2,3-dichlorobutane? [AIEEE-2005]
(A) Tautomerism (B) Optical (C) Geometric (D) Structural
13. Increasing order of stability among the three main conformations (i.e. Eclipse, Anti, Gauche) of
2-fluoroethanol is [AIEEE-2006]
(A) Eclipse, Gauche, Anti (B) Gauche, Eclipse, Anti
(C) Eclipse, Anti, Gauche (D) Anti, Gauche, Eclipse
14. Which of the following molecules is expected to rotate the plane of plane polarized light ?
[AIEEE-2007]
CHO COOH
H2N NH2
(A) HO H (B) (C) H H (D) H2N H
SH
Ph Ph H
CH2OH
15. Which one of the following conformation of cyclohexane is chiral? [AIEEE-2007]

(A) Twist boat (B) Rigid (C) Chair (D) Boat
HO2C CO2H
16. The absolute configuration of is [AIEEE-2008]
HO H OH
H
(A) S, S (B) R, R (C) R, S (D) S, R
17. The alkene that exhibits geometrical isomerism is : [AIEEE-2009]

(A) 2-butene (B) 2-methyl-2-butene (C) propene (D) 2-methyl propene
18. The number of stereoisomers possible for a compound of the molecular formula [AIEEE-2009]
CH3 – CH = CH – CH(OH) – Me is :
(A) 4 (B) 6 (C) 3 (D) 2
ORGANIC CHEMISTRY
19. The IUPAC name of neopentane is : [AIEEE-2009]

(A) 2-methylpropane (B) 2, 2-dimethylbutane
(C) 2-methylbutane (D) 2, 2-dimethylpropane
20. One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular
mass of 44 u. The alkene is [AIEEE-2010]
(A) 2-butene (B) ethene (C) propene (D) 1-butene
21. Identify the compound that exhibits tautomerism. [AIEEE-2011]
(A) 2-Butene (B) Lactic acid (C) 2-Pentanone (D) Phenol
22. Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms the
presence of : [AIEEE-2011]
(A) two ethylenic double bonds (B) a vinyl group
(C) an isopropyl group (D) an acetylenic triple bond
23. How many chiral compounds are possible on monochlorination of 2- methyl butane?
[AIEEE-2012]
(A) 8 (B) 2 (C) 4 (D) 6
24. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of
mono substituted alkyl halide ? [AIEEE-2012]
(A) Tertiary butyl chloride (B) Neopentane
(C) Isohexane (D) Neohexane
25. The product of the reaction given below is : [JEE Mains-2016]
1. NBS/h
X
2. H2O/K2CO3
OH O CO2H
(A) (B) (C) (D)
26. The absolute configuration of [JEE Mains-2016]
CO2H
H OH
H Cl
CH3
is :
(A) (2R, 3S) (B) (2S, 3R) (C) (2S, 3S) (D) (2R, 3R)
ORGANIC CHEMISTRY
27. In the following structure, the double bonds are marked as I, II, III and IV
II [JEE Mains Online-2017]
III
I IV
(A) III (B) I (C) I and III (D) III and IV
28. The total number of optically active compounds formed inthet following reaction is :
[JEE Mains Online, 2018]
O
HBr
(A) Two (B) Four (C) Six (D) Zero
29. The number of chiral carbons present in the molecule given below is ..........
30. The number of chiral centres present in threonine is ............... [JEE Mains Online, 2020]
31. Among the following compounds, geometrical isomerism is exhibited by :

CHCl CHCl CHCl CH2
(1) (2) (3) (4)

CH3 H3C CH3
CI
31. Which of the follwing compounds shows geometrical isomerism ? [JEE Mains Online, 2020]
(1) 4-methylpent-1-ene (2) 2-methylpent-2-ene
(3) 4-methylpent-2-ene (4) 2-methylpent-1-ene
ORGANIC CHEMISTRY
[JEE-ADVANCED]
1. Isomers which can be interconverted through rotation around a single bond are [JEE 1992]
(A) Conformers (B) Diastereomers (C) Enantiomers (D) Positional isomers
2. The shows: [JEE 1995(Scr.)]
(A) geometrical isomerism (B) optical isomerism

(C) geometrical & optical isomerism (D) tautomerism
3. How many optically active stereoisomers are possible for butane-2,3-diol? [JEE 1997]
(A) 1 (B) 2 (C) 3 (D) 4
4. When cyclohexane is poured on water, it floats, because: [JEE 1997]

(A) cyclohexane is in 'boat' form (B) cyclohexane is in 'chair' form
(C) cyclohexane is in 'crown' form (D) cyclohexane is less dense than water
5. Which of the following compounds will show geometrical isomerism? [JEE 1998]
(A) 2-butene (B) propene (C) 1-phenylpropene (D) 2-methyl-2-butene
6. Which of the following compounds will exhibit geometrical isomerism? [JEE 2000 (Scr.)]
(A) 1-Phenyl-2-butene (B) 3-Phenyl-1-butene
(C) 2-Phenyl-1-butene (D) 1,1-Diphenyl-1-propene
7. The number of isomers for the compound with molecular formula C2BrClFI is [JEE 2001 (Scr.)]
(A) 3 (B) 4 (C) 5 (D) 6
8. Which of the following compounds exhibits stereoisomerism? [JEE 2002 (Scr.)]
(A) 2-methylbutene-1 (B) 3-methylbutyne-1
(C) 3-methylbutanoic acid (D) 2-methylbutanoic acid
9. In the given conformation, if C2 is rotated about C2–C3 bond anticlockwise by an angle of 120° then
the conformation obtained is 4 [JEE 2004 (Scr.)]
CH3
H H
3
2
H H
1CH3
(A) fully eclisped conformation (B) partially eclipsed conformation

(C) gauche conformation (D) staggered conformation
10. The number of structural isomers for C6H14 is [JEE 2007]

(A) 3 (B) 4 (C) 5 (D) 6
ORGANIC CHEMISTRY
11. Statement-1 : Molecules that are not superimposable on their mirror images are chiral.[JEE 2007]
Statement-2 : All chiral molecules have chiral centres.
(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.
12. The correct statement(s) about the compound given below is (are) [JEE 2008]
(A) The compound is optically active Cl H
(B) The compound possesses centre of symmetry
CH3
(C) The compound possesses plane of symmetry H3C
(D) The compound possesses axis of symmetry H
Cl
13. The correct statement(s) concerning the structures E, F and G is (are) [JEE 2008]
H3C O H3C OH H 3C CH3
H 3C CH3 H 3C CH3 H3C OH

(E) (F) (G)
(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
14. The correct statement(s) about the compound H3C(HO)HC – CH = CH – CH(OH)CH3(X) is (are)
(A) The total number of stereoisomers possible for X is 6 [JEE 2009]
(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
15. In the Newman projection for 2,2-dimethylbutane [JEE 2010]
X
H3C CH3
H H
Y
X and Y can respectively be

(A) H and H (B) H and C2H5 (C) C2H5 and H (D) CH3 and CH3
16. Amongst the given options, the compound(s) in which all the atoms are in one plane in all the possible
conformations (if any), is (are) [JEE 2011]
H H H
C—C
(A) (B) H — C C—C
H2C CH2 CH2
(C) H2C = C = O (D) H2C = C = CH2
ORGANIC CHEMISTRY
17. In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) : [JEE 2012]
(A) sp and sp 3 (B) sp and sp 2 (C) only sp2 2
(D) sp and sp3
18. The number of optically active products obtained from the complete ozonolysis of the given compound
is : CH H
[JEE 2012]
3
CH3 – CH = CH – C – CH = CH – C – CH = CH – CH3
H CH3
(A) 0 (B) 1 (C) 2 (D) 4

19. Which of the following molecules, in pure form, is (are) unstable at room temperature ?[JEE 2012]
O O
(A) (B) (C) (D)
20. Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct ?
[JEE 2012]
HO HO Cl
H H CH3 CH3
H OH H OH HO H
Cl CH3
HO H H OH HO H
HO H HO H
CH3 Cl CH3 Cl Cl
M N O P Q
(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
21. For 'invert sugar', the correct statement(s) is(are) [JEE Advance 2016]
(Given : specific rotations of (+)-sucrose, (+)-maltose, L-(–)-glucose and L-(+)-fructose in aqueous
solution are +66º, +140º, –52º and +92º, 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 sugar' is –20º
(D) on reaction with Br2 water, 'invert sugar' forms saccharic acid as one of the products
ORGANIC CHEMISTRY
22. For the given compound X, the total number of optically active stereoisomers is_____.
[JEE Advance 2018]
HO
HO
This type of bond indicates that the configuration at the specific
carbon and the geometry of the double bond is fixed
HO HO This type of bond indicates that the configuration at the specific

X
carbon and the geometry of the double bond is NOT fixed
23. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the molecular
formula C4H8O is _______. [JEE Advance 2019]
24. Newman projections P, Q, R and S are shown below : [JEE Advance 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
25. The Fischer projection of D-erythrose is shown below : [JEE Advance 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.
ORGANIC CHEMISTRY
Column – I Column – II
P. 1. Diastereomer
Q. 2. Identical
R. 3. Enantiomer
S.
(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
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. C 2. C 3. D 4. B 5. D 6. D 7. D
8. A 9. A 10. B 11. B 12. B 13. C 14. A
15. A 16. B 17. A 18. A 19. D 20. A 21. C
22. B 23. C 24. B 25. B 26. B 27. B 28. B
29. 5 30. 2 31. 1 (Answer should be 1 and 3 both) 31. 3
[JEE-ADVANCED]
1. A 2. B 3. B 4. D 5. A, C 6. A 7. D
8. D 9. C 10. C 11. C 12. A, D 13. B, C, D
14. A, D 15. B, D 16. B, C 17. B 18. A 19. BC
20. ABC 21. B,C 22. 7 23. 10 24. C 25. C
ORGANIC CHEMISTRY
GENERAL ORGANIC CHEMISTRY
[JEE-MAIN / AIEEE]
1. In the following benzyl/alkyl system
R – CH = CH2 or (R is alkyl group)
increasing order of inductive effect is – [AIEEE-2002]
(A) (CH3)3 C – > (CH3)2 CH –> CH3CH2—
(B) (CH3CH2 – > (CH3)2 CH –> (CH3)3C —
(C) (CH3)2 CH – > CH3CH2 –> (CH3)3C—
(D) (CH3)C – > CH3CH2 –> (CH3)2CH—
CH 3
|
2. When – CH3, CH3  CH  & CH 3  C  groups are introduced on benzene ring then correct order
| |
CH 3 CH 3
of their inductive effect is - [AIEEE-2002]
CH 3 CH 3
| |
(A) CH3– > CH 3  CH  > CH 3  C  (B) CH 3  C  > CH3  CH  > CH3–
| | | |
CH 3 CH 3 CH 3 CH 3
CH 3 CH 3
| |
(C) CH 3  CH  > CH3– > CH 3  C  (D) CH 3  C  > CH3 – > CH3  CH 
| | | |
CH 3 CH 3 CH 3 CH 3
3. The correct order of increasing basic no. of the bases NH3, CH3NH2 and (CH3)2NH is –
[AIEEE-2003]
(A)NH3 < CH3NH2 < (CH3)2NH (B) CH3NH2 < (CH3)2NH < NH3
(C) CH3NH2 < NH3 < (CH3)2NH (D) (CH3)2NH < NH3 < CH3NH2
4. Consider the acidity of the carboxylic acids : [AIEEE-2004]

(a) PhCOOH (b) o – NO2C6H4COOH
(c) p – NO2C6H4COOH (d) m – NO2C6H4COOH
Which of the following order is correct ?
(A) a > b > c > d (B) b > d > c > a (C) b > d > a > c (D) b > c > d > a
5. Which of the following is the strongest base - [AIEEE-2004]
(A) (B) (C) (D)
ORGANIC CHEMISTRY
6. Amongst the following the most basic compound is– [AIEEE-2005]

(A) aniline (B) benzylamine (C) p–nitroaniline (D) acetanilide
7. The increasing order of stability of the following free radicals is – [AIEEE 2006]
   
(A) (C6H5)3 C < (C6H5)2 C H < (CH3)3 C < (CH3)2 C H
   
(B) (C6H5)2 C H < (C6H5)3 C < (CH3)3 C < (CH3)2 C H
   
(C) (CH3)2 C H < (CH3)3 C < (C6H5)3 C < (C6H5)2 C H
   
(D) (CH3)2 C H < (CH3)3 C < (C6H5)2 C H < (C6H5)3 C
8. The correct order of increasing acid strength of the compounds [AIEEE 2006]
Me
(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d) CO2H is
Me
(A) d < a < c < b (B) d < a < b < c (C) a < d < c < b (D) b < d < a < c
9. Which one of the following is the strongest base in aqueous solution ? [AIEEE-2007]
(A) Trimethylamine (B) Aniline (C) Dimethylamine (D) Methylamine
   
10. Arrange the carbanions, (CH 3)3 C , C Cl3 , (CH3)2 C H , C6H5 C H , in order of their decreasing
2
stability- [AIEEE 2009]
   
(A) (CH3)2 C H > C Cl3 > C6H5 C H > (CH3)3 C
2
   
(B) C Cl3 > C6H5 C H2 > (CH3)2 C H > (CH3)3 C
   
(C) (CH3)3 C > (CH3)2 C H >C6H5 C H > C Cl3
2
   
(D) C6H5 C H > C Cl3 > (CH3)3 C > (CH3)2 C H
2
11. The correct order of increasing basicity of the given conjugate bases (R = CH3) is : [AIEEE 2010]
       
(A) RCO O  N H 2  HC  C  R (B) RCO O  HC  C  N H 2  R
       
(C) RCO O  HC  C  R  N H 2 (D) R  HC  C  RCO O  N H 2
12. The strongest acid amongst the followng compounds is [AIEEE 2011]
(A) CH3COOH (B) HCOOH
(C) CH3CH2CH(Cl)CO2H (D) ClCH2CH2CH2COOH
ORGANIC CHEMISTRY
13. Arrange the following compounds in order of decreasing acidity : [JEE Main 2013]
OH OH OH OH
Cl CH3 NO2 OCH3

(I) (II) (III) (IV)
(A) I > II > III > IV (B) III > I > II > IV
(C) IV > III > I > II (D) II > IV > I > III
14. The order of stability of the following carbocations: [JEE Main 2013]
CH2
CH2 = CH – CH2 ; CH3 – CH2 – CH 2 ;
(I) (II)
is
(A) II > III > I (B) I > II > III (C) III > I > II (D) III > II > I
15. Considering the basic strength of amines in aqueous solution, which one has the smallest pKb value?
[JEE Main 2014]
(A) CH3NH2 (B) (CH3)3N (C) C6H5NH2 (D) (CH3)2NH
16. Which of the following molecules is least resonance stabilized ? [JEE Main 2017]
(A) (B) N (C) (D)

O
O
17. The increasing order of basicity of the following compounds is : [JEE Main 2018]
NH2
(a) NH2 (b) NH (c) (d) NHCH3
NH
(A) (b) < (a) < (d) < (c) (B) (d) < (b) < (a) < (c)
(C) (a) < (b) < (c) < (d) (D) (b) < (a) < (c) < (d)
18. The predominant form of histamine present in human blood is (pKa, Histidine = 6.0) [JEE Main 2018]
H H
N
N
(A) (B) NH3
N NH2
H N
H H
N N
NH3
(C) NH2 (D)
N
N H
ORGANIC CHEMISTRY
19. Which of the following compounds will show the maximum 'enol' content ? [JEE Main 2019]
(A) CH3COCH3 (B) CH3COCH2COCH3
(C) CH3COCH2COOC2H5 (D) CH3COCH2CONH2
20. Which amongst the following is the strongest acid ? [JEE Main 2019]
(A) CHBr3 (B) CHI3 (C) CHCl3 (D) CH(CN)3
21. The correct order for acid strength of compounds : [JEE Main 2019]
CH  CH, CH3 – C  CH and CH2 = CH2 is as follows :
(A) CH3 – C  CH > CH2 = CH2 > HC  CH
(B) CH3 – C  CH > CH  CH > CH2 = CH2
(C) HC  CH > CH3 – C  CH > CH2 = CH2
(D) CH  CH > CH2 = CH2 > CH3 – C  CH
22. Arrange the following labelled hydrogens in decreasing order of acidity : [JEE Main 2020]
(A) b > c > d > a (B) c > b > a > d (C) b > a > c > d (D) c > b > d > a
23. If you spill a chemical toilet cleaning liquid on your hand, your first aid would be: [JEE Main 2020]
(A) vinegar (B) aqueous NaOH (C) aqueous NaHCO3 (D) aqueous NH3
24. Which one of the following compounds possesses the most acidic hydrogen ? [JEE Main 2020]
(A) H3C – C  C – H (B)
(C) (D)
25. Consider the following molecules and statements related to them : [JEE Main 2020]
(A) (B)
(a) (B) is more likely to be crystalline than (A) (b) (B) has higher boiling point than (A)
(c) (B) dissolves more readily than (A) in water
Identify the correct option from below :
(A) only (a) is true (B) (a) and (b) are true (C) (b) and (c) are true (D) (a) and (c) are true
ORGANIC CHEMISTRY
26. The decreasing order of reactivity of the following organic molecules towards AgNO3 solution is :
(A) (C) > (D) > (A) > (B) (B) (A) > (B) > (C) > (D) [JEE Main 2020]
(C) (B) > (A) > (C) >(D) (D) (A) > (B) > (D) > (C)
27. Among the following compounds, which one has the shortest C-Cl bond ? [JEE Main 2020]
(A) (B) (C) (D) H3C – Cl
28. Which of the following compounds will form the precipitate with aq. AgNO3 solution most readily ?
[JEE Main 2020]
(A) (B) (C) (D)
29. The increasing order of basicity of the following compounds is : [JEE Main 2020]
(A) (B) < (A) < (C) < (D) (B) (A) < (B) < (C) < (D)
(C) (D) < (A) < (B) < (C) (D) (B) < (A) < (D) < (C)
30. The increasing order of the acidity of the -hydrogen of the following compounds is :
[JEE Main 2020]
(A) (C) < (A) < (B) < (D) (B) (B) < (C) < (A) < (D)
(C) (A) < (C) < (D) < (B) (D) (D) < (C) < (A) < (B)
ORGANIC CHEMISTRY
31. The increasing order of boiling points of the following compounds is : [JEE Main 2020]
OH OH OH OH
CH3 NO2 NH2 OCH3

I II III IV
(A) I < IV < III < II (B) IV < I < II < III (C) I < III < IV < II (D) III < I < II < IV
32. The increasing order of pKb values of the following compounds is : [JEE Main 2020]
N(CH3) 2
N(CH3) 2 NHCH3 NHCH3
(I) (II) (III) (IV)

CN OH
OCH3
(A) II < I < III < IV (B) II < IV < III < I (C) I < II < IV < III (D) I < II < III < IV
[JEE-ADVANCED]
1. Phenol is less acidic than [JEE 1986]
(A) Acetic acid (B) p-methoxy phenol (C) p-nitrophenol (D) Ethanol
2. The bond between carbon atom (1) and carbon atom (2) in compound [JEE 1987]
N  C  CH  CH 2
1 2
involves the hybridisations as

(A) sp2 and sp2 (B) sp3 and sp (C) sp and sp2 (D) sp and sp
3. Polarisation of electrons in acrolein may be written as [JEE 1988]


O O
 ||  ||
(A) H 2C  CH  C  H (B) H 2C  CH  C  H


O O
  ||  ||
(C) H 2C  CH  C  H (D) H 2C  CH  C  H
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
ORGANIC CHEMISTRY
5. Amongst the following, the most basic compound is [JEE 1990]
(A) benzylamine (B) aniline (C) acetaniline (D) p-nitroaniline
6. The shape of (CH3)+ is ______________ [JEE 1990]
7. The hybridisation of carbon atoms in C–C single bond H–C C–CH=CH2 is [JEE 1991]
(A) sp3– sp3 (B) sp2 – sp3 (C) sp – sp3 (D) sp – sp2
8. What is the decreasing order of strength of the base? [JEE 1992]

OH¯ , NH2¯, H – C  C¯ and CH3 – CH2¯
(A) CH3 CH2¯ > NH2 ¯ > H – C  C¯ > OH¯
(B) H – C  C¯ > CH3 – CH2¯ > NH2 ¯ > OH¯
(C) OH¯ > NH2¯ > H – C  C¯ > CH3 – CH2¯
(D) NH2¯ > H – C  C¯ > OH¯ > CH3 – CH2¯
9. The bond dissociation energy needed to form the benzyl radical from toluene is _________ than the
formation of the methyl radical from methane [JEE 1994]
10. The kind of delocalisation involving sigma bond orbitals is called ___________ [JEE 1994]
11. Arrange the following in the order of their increasing basicity : p-toludine, N,N-dimethyl-p-toluidine,
p-nitroaniline, aniline. [JEE 1995]
12. In the following compounds: [JEE 1996]
The order of acidity is:

(A) III > IV > I > II (B) I > IV > III > II (C) II > I > III > IV (D) IV > III > I > II
13. Although phenoxide ion has more number of resonating structures than benzoate ion, benzoic acid is a
stronger acid than phenol. Why? [JEE 1997]
14. Among the following compounds, the strongest acid is [JEE 1998]
(A) HC  CH (B) C6H6 (C) C2H6 (D) CH3OH
15. The most unlikely representation of resonance structure of p-nitrophenoxide ion is: [JEE 1998]
(A) (B) (C) (D)
ORGANIC CHEMISTRY
16. Give reasons for the following in one or two sentences.
The central carbon - carbon bond in 1,3 butadiene is shorter than that of n-butane. [JEE 1998]
17. Explain, why o-hydroxybenzaldehyde is a liquid at room temperature while p-hydroxybenzaldehyde is a

high melting solid [JEE 1999]
18. Give reasons for the following [JEE 2000]

CH2 = CH– is more basic than HCC–
19. The compound in which C uses only its sp3-hybrid orbitals for bond formation is : [JEE 2000]
(A) HCOOH (B) (H2N)2CO (C) (CH3)3COH (D) CH3CHO
20. Which of the following has the most acidic hydrogen? [JEE 2000]
(A) 3-hexanone (B) 2,4-hexanedione (C) 2,5-hexaedione (D) 2,3-hexaedione
21. Amongst the following the strongest base is: [JEE 2000]
(A) C6H5NH2 (B) p-O2NC6H4NH2 (C) m-O2NC6H4NH2 (D) C6H5CH2NH2
22. The correct order of basicities of the following compounds is: [JEE 2001]
O
||
CH3CH2NH2 (CH3)2NH CH 3CNH 2
(1) (2) (3) (4)
(A) 2 > 1 > 3 > 4 (B) 1 > 3 > 2 > 4 (C) 3 > 1 > 2 > 4 (D) 1 > 2 > 3 > 4
23. Identify the correct order of boiling points of the following compounds. [JEE 2002]
(1) CH3CH2CH2CH2OH (2) CH3CH2CH2CHO
(3) CH3CH2CH2COOH
(A) 1 > 2 > 3 (B) 3 > 1 > 2 (C) 1 > 3 > 2 (D) 3 > 2 > 1
24. Which of the following acids has the smallest dissociation constant? [JEE 2002]
(A) CH3CHFCOOH (B) FCH2CH2COOH
(C) BrCH2CH2COOH (D) CH3CHBrCOOH
COOH OH
25.
H
O2N OH
when X is made to react with 2 eq. of NaNH2 the product formed will be: [JEE 2003]
ORGANIC CHEMISTRY
OOC OH OOC
O
(A) (B)
 H
O2 N OH O2 N OH
OH O
OOC
HOOC
(C) (D)
H 
O OH
O2N O2N
26. Which of the following represent the given mode of hybridisation sp2, sp2, sp, sp from left to right ?
[JEE 2003]
(A) H2C = CH–CN (B) H2C=C=CH–CH3
(C) HCC–CCH (D) HCC–CH=CH2
27. Maximum dipole moment will be of : [JEE 2003]

(A) CCl4 (B) CHCl3 (C) CH2Cl2 (D) CH3Cl
28. [JEE 2004]
Correct order of acidic strength is:

(A) x > y > z (B) z > y > x (C) y > z > x (D) x > z > y
29. For 1-methoxy-1,3-butadiene, which of the following resonating structure is the least stable?
[JEE 2005]
   
(A) H 2C CH  CH  CH  O  CH 3 (B) H 2C CH  CH  CH  O  CH 3
   
(C) H 2C  CH  CH  CH  O  CH 3 (D) H 2C  CH  CH  CH  O CH 3
ORGANIC CHEMISTRY
30. When benzene sulfonic acid and p-nitrophenol are treated with NaHCO3, the gases released respectively
are [JEE 2006]
(A) SO2, NO2 (B) SO2, NO (C) SO2, CO2 (D) CO2, CO2
31. Among the following, the least stable resonance structure is [JEE 2007]
O O
N N
(A) (B)
O O
O O
N N
(C) (D)
O O
32. The correct stability order for the following species is [JEE 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)
33. Hyperconjugation involves overlap of the following orbitals [JEE 2008]

(A)  –  (B)  – p (C) p – p (D)  – 
34. The correct acidity order of the following is : [JEE 2008]
OH COOH
OH COOH
(I) (II) (III) (IV)

Cl CH3
(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)
35. The correct stability order of the following resonance structrue is : [JEE 2009]
(I) H2C=N=N (II) H2C – N = N
(III) H2C – N N (IV) H2C – N = N
ORGANIC CHEMISTRY
(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)
36. 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
37. The total number of contributing structures showing hyperconjugation (involving C–H bonds ) for the
following carbocation is [JEE 2011]
38. Which of the following molecules, in pure from, is (are) unstable at room temperature ?[JEE 2012]
(A) (B) (C) (D)
39. The compound that does NOT liberate CO2 , on treatment with aqueous sodium bicarbonate solution,
is : [JEE Advance 2013]
(A) Benzoic acid (B) Bezenesulphonic acid
(C) Salicylic acid (D) Carbolic acid (Phenol)
40. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to
(A)   p (empty) and   * electron delocalistaions. [JEE Advance 2013]
(B) * and  electron delocalisations
(C)  p (filled) and  electron delocalisations
(D) p (filled) * and * electron delocalisations
41. The total number of lone-pairs of electrons in melamine is [JEE Advance 2013]
42. Hydrogen bonding plays a central role in the following phenomena : [JEE Advance 2014]
(A) Ice floats in water.
(B) Higher Lewis basicity of primary amines than tertiary amines in aqueous solutions
(C) Formic acid is more acidic than acetic acid.
(D) Dimerisation of acetic acid in benzene.
43. The number of resonance structures for N is : [JEE Advance 2015]
OH
NaOH
N
ORGANIC CHEMISTRY
44. The correct order of acidity for the following compound is : [JEE Advance 2016]
CO2 H
CO2 H CO2 H CO2 H
HO OH OH
OH OH
I II III IV
(A) I > II > III > IV (B) III > I > II > IV (C) III > IV > II > I (D) I > III > IV > II
45. Among the following, the number of aromatic compound(s) is [JEE Advance 2017]
  
 
46. The order of basicity among the following compounds is [JEE Advance 2017]
NH NH2
N NH HN N
H3C NH2 H2N NH
(I) (II) (III) (IV)
(A) I > IV > III > II (B) II > I > IV > III (C) IV > I > II > III (D) IV > II > III > I
47. With respect to the compounds I–V, choose the correct statement(s). [JEE Advance 2020]
(A) The acidity of compound I is due to delocalization in the conjugate base.

(B) The conjugate base of compound IV is aromatic.
(C) Compound II becomes more acidic, when it has a –NO2 substituent.
(D) The acidity of compounds follows the order I > IV > V > II > III.
ORGANIC CHEMISTRY
48. Consider the following four compounds I, II, III, and IV. [JEE Advance 2020]
I II III IV
Choose the correct statement(s).
(A) The order of basicity is II > I > III > IV.
(B) The magnitude of pKb difference between I and II is more than that between III and IV.
(C) Resonance effect is more in III than in IV
(D) Steric effect makes compound IV more basic than III.
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. A 2. B 3. A 4. D 5. D 6. B 7. D
8. B 9. C 10. B 11. B 12. C 13. B 14. C
15. D 16. C 17. A 18. B 19. B 20. D 21. C
22. A 23. C 24. C 25. B 26. C 27. B 28. A
29. D 30. D 31. A 32. C
[JEE-ADVANCED]
1. AC 2. C 3. D 4. B 5. A 6. Triangular planar
7. D 8. A 9. less 10. hyperconjugation 11. 2>1>4>3
12. D 13. Better resonance occurs in Benzoic acid 14. D 15. C
16. Because of Resonance
17. Becoz of intramolecular H-bonding is o-hydroxybenzaldehyde
18. Acidic strength : CH  CH > CH2=CH2
Basic Strength : CH  C < CH2=CH 19. C 20. B 21. D 22. B

23. B 24. C 25. C 26. A 27. D 28. D 29. C
30. D 31. A 32. D 33. B 34. A 35. B 36. C
37. 6 38. BC 39. D 40. A 41. 6 42. ABD 43. 9
44. A 45. 5 46. C 47. ABC 48. CD
ORGANIC CHEMISTRY
HYDROCARBON
[JEE-MAIN / AIEEE]
1. The compound
H3C  C = CH– CH2 – CH3Vigorous
  oxidation
 product, here product is [AIEEE-2002]
|
H3 C
(A) CH3COOH & CH3 – C – CH3 (B) CH3 – CH2 – COOH & CH3 – C  O
|| |
O CH 3
(C) CH3 – CH2 – COOH only (D) HCOOH & CH3 – C – CH3
||
O
2. Reaction
H – C  C – H + HOCl  product, here product will be - [AIEEE-2002]
(A) CHCl2 – CHO (B) CHO – CHO (C) CH – Cl = CHCl (D) CHCl2 – CHCl2
3. Acetylene does not react with - [AIEEE-2002]

(A) NaNH2 (B) NaOH (C) Na metal (D) Ammonical AgNO3
4. Butene-1 may be converted to butane by reaction with – [AIEEE-2003]

(A) Zn – Hg (B) Pd / H2 (C) Zn – HCl (D) Sn – HCl
5. During dehydration of alcohols to alkenes by heating with conc. H2SO4 the initiation step is -
(A) Elimination of water [AIEEE-2003]
(B) Formation of an ester
(C) Protonation of alcohol molecule
(D) Formation of carbocation
6. On mixing a certain alkane with chlorine and irradiating it with ultraviolet light, it forms only one
monochloroalkane. This alkane could be – [AIEEE-2003]
(A) Isopentane (B) Neopentane (C) Propane (D) Pentane
7. Which one of the following has the minimum boiling point ? [AIEEE-2004]
(A) n – Butane (B) 1– Butyne (C) 1– Butene (D) isobutane
8. Amongst the following compounds, the optically active alkane having lowest molecular mass is-
[AIEEE-2004]
CH3
|
(A) CH3–CH2–CH2–CH3 (B) CH3  CH2  CH  CH3
(C) (D) CH3–CH2 – C  CH
ORGANIC CHEMISTRY
9. Reaction of one molecule of HBr with one molecule of 1,3–butadiene at 40ºC given predominantly
(A)1–bromo–2–butene under thermodynamically controlled conditions [AIEEE-2005]
(B) 3–bromobutene under kinetically controlled conditions
(C) 1–bromo–2–butene under kinetically controlled conditions
(D) 3–bromobutene under thermodynamically controlled conditions
10. Acid catalyzed hydration of alkenes except ethene leads to the formation of – [AIEEE-2005]
(A) secondary or tertiary alcohol (B) primary alcohol
(C) mixture of secondary and tertiary alcohols (D) mixture of primary and secondary alcohols
11. Reaction of trans 2-phenyl-1 bromocyclopentane on reaction with alcoholic KOH produces
(A) 2-phenylcyclopentene (B) 1-phenylcyclopentene [AIEEE 2006]
(C) 3-phenylcyclopentene (D) 4-phenylcyclopentene
Me

Me
12. N
OH
n-Bu Et
The alkene formed as a major product in the above elimination reaction is [AIEEE 2006]
Me Me
(A) CH2 = CH2 (B) (C) (D) Me
13. Which of the following reactions will yield 2, 2-dibromopropane? [AIEEE 2007]
(A) CH3 – C  CH + 2HBr  (B) CH3CH = CHBr + HBr 
(C) CH  CH + 2HBr  (D) CH3 – CH = CH2 + HBr 
14. In the following sequence of reactions, the alkene affords the compound ‘B’
CH3CH = CHCH3 O3  A H2

O
 B, The compound B is [AIEEE 2008]
Zn
(A) CH3COCH3 (B) CH3CH2COCH3

(C) CH3CHO (D) CH3CH2CHO
15. The treatment of CH3MgX with CH3C  C – H produces [AIEEE 2008]

H H
(A) CH3 C  C – CH3 (B) CH3 C C CH3
(C) CH4 (D) CH3 –CH = CH2

16. The hydrocarbon which can not react with sodium in liquid ammonia to give H2 is [AIEEE 2008]
(A) CH3CH2 C CH (B) CH3CH = CHCH3
(C) CH3CH2C  CCH2CH3 (D) CH3CH2CH2C  CCH2CH2CH3
17. Out of the following, the alkene that exhibits optical isomerism is : [AIEEE 2010]
(A) 3-methyl-1-pentene (B) 2-methyl-2-pentene
(C) 3-methyl-2-pentene (D) 4-methyl-1-penten
ORGANIC CHEMISTRY
18. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of
mono substituted alkyl halide? [AIEEE 2012]
(A) Isohexane (B) Neohexane
(C) Tertiary butyl chloride (D) Neopentane.
19. 2–Hexyne gives trans-2-Hexene on treatment with : [AIEEE 2012]

(A) Pd/BaSO4 (B) LiAlH4
(C) Pt/H2 (D) Li/NH3
20. A gaseous hydrocarbon gives upon combustion 0.72 g of water and 3.08 g of CO2. The empirical
formula of the hydrocarbon is: [JEE Main 2013]
(A) C3H4 (B) C6H5 (C) C7H8 (D) C2H4
21. Which compound would give 5 – keto – 2 – methyl hexanal upon ozonolysis ?
[JEE Main 2015]
CH3 CH3
CH3 CH3
(A) (B) H3C (C) CH3 (D)
CH 3 CH3
22. The product of the reaction given below is: [JEE Main 2016]
1. NBS/hv
X
2. H2O/K2CO3
CO2H OH O
(A) (B) (C) (D)
23. The reaction of propene with HOCl (Cl2 + H2O) proceeds through the intermediate:
(A) CH3–CHCl–CH2+ (B) CH3 –CH+–CH2 –OH [JEE Main 2016]
+
(C) CH3– CH –CH2 –Cl (D) CH3– CH(OH) – CH2 +
24. The major product obtained in the following reaction is : [JEE Main 2017]
Br
H t
BuOK
C6H5

C 6H 5
(+)
(A) C6H5CH = CHC6H5 (B) (+) C6H5CH (OtBu) CH2C6H5

(C) (–) C6H5CH(OtBu) CH2C6H5 (D) (±) C6H5CH(OtBu) CH2C6H5
ORGANIC CHEMISTRY
25. 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) Zero (B) Two (C) Four (D) Six
26. The trans-alkenes are formed by the reduction of alkynes with: [JEE Main 2018]
(A) Na/liq.NH3 (B) Sn-HCl (C) H2-Pd/C, BaSO4 (D) NaBH4
27. In the following skew conformation of ethane, H' – C – C – H'' dihedral angle is [JEE MAIN 2019]
H
H H 29°
H
H H
(A) 58° (B) 149° (C) 151° (D) 120°
28. Which of these factors does not govern the stability of a conformation in acyclic compounds ?
(A) Electrostatic forces of interaction [JEE MAIN 2019]
(B) Torsional strain
(C) Angle strain
(D) Steric interactions
29. Consider the following reactions, [JEE MAIN 2019]
Ag 2O
ppt
A Hg /H
2+ +
NaBH4 ZnCl2
B C conc. Hcl Turbidity within
5 minutes
A is
(A) CH  CH (B) CH3 – C  C – CH3
(C) CH3 – C  CH (D) CH2 = CH2
30. But-2-ene on reaction with alkaline KMnO4 at elevated temperature followed by acidification will give
(A) [JEE MAIN 2019]
OH OH
(B) one molecule of CH3CHO and molecule of CH3COOH
(C) 2 molecules of CH3COOH
(D) 2 molecules of CH3CHO
ORGANIC CHEMISTRY
31. The major product of the following addition reaction is [JEE MAIN 2019]
Cl2 / H 2 O
H3C – CH = CH2  
(A) CH 3 – CH – CH 2 (B) CH 3 – CH – CH 2
Cl OH OH Cl
O
O
(C) H 3C (D) H3C CH3
32. The major product of the following reaction is [JEE MAIN 2019]
(i) DCI (1 equiv.)
CH3C  CH (ii) DI

(A) CH3CD(Cl)CHD(I) (B) CH3CD2CH(Cl)(I)

(C) CH3CD(l)CHD(Cl) (D) CH3C(I)(Cl)CHD2
33. Which one of the following alkenes when treated with HCl yields majorily an anti Markownikov
product ? [JEE MAIN 2019]
(A) Cl – CH = CH2 (B) H2N – CH = CH2
(C) CH3O – CH = CH2 (D) F3C – CH = CH2
34. The major product in the following reaction is : [JEE MAIN 2020]
(A) (B) (C) (D)
35. The major product of the following reaction is: [JEE MAIN 2020]
OH
CH3
Conc. HNO3 + Conc. H2SO4
NO2
OH OH
CH3 NO2 CH3 NO2

(A) (B)
NO2 NO2
OH
OH
CH3
CH3
(C) NO2 (D)
O2 N NO2
NO2
ORGANIC CHEMISTRY
36. Which of the following compounds produces an optically inactive compound on hydrogenation ?
[JEE MAIN 2020]
(A) (B) (C) (D)
37. The total number of monohalogenated organic products in the following (including stereoisomers) reaction
is__________. [JEE MAIN 2020]
38. [P] on treatment with Br2/FeBr3 in CCl4 produced a single isomer C8H7O2Br while heating [P] with
sodalime gas toluene. The compound [P] is : [JEE MAIN 2020]
(A) (B) (C) (D)
39. The major product [C] of the following reaction sequence will be : [JEE MAIN 2020]
(A) (B)
(C) (D)
40. In the following reaction sequence the major product A and B are : [JEE MAIN 2020]
(A) A = ;B=
ORGANIC CHEMISTRY
(B) A = ;B=
(C) A = ;B=
(D) A = ;B=
41. The final major product of the following reaction is : [JEE MAIN 2020]
Me
(i) Ac2O/ Pyridine
(ii) Br2 , FeCI3
(iii) OH- / 
NH2
Br
Me Me Br Me
Me
(A) (B) Br (C) (D) Br

NH2 NH2 NH2
NH2
42. The major product of the following reaction is : [JEE MAIN 2020]
CH3
2HBr
NO2
CH3 CH3 Br CH3

H3C Br
Br Br
(A) (B) (C) (D)

Br Br
Br Br
NO2 NO2 CH3
NO2
ORGANIC CHEMISTRY
43. The major product obtained from the following reaction is : [JEE MAIN 2020]
+2 +
Hg |H
O2 N C C OCH 3
H2O
OCH 3 OH
O O
(A) (B)
O 2N O 2N
OCH 3 OH
(C) (D)
O O
O 2N O 2N
44. The increasing order of the boiling points of the major product A, B and C of the following reactions
will be [JEE MAIN 2020]
(a)
(b)
(c)
(A) A < B < C (B) A < C < B (C) B < C < A (D) C < A < B
[JEE-ADVANCED]
1. Alcoholic solution of KOH is a specific reagent for – [IIT 1990]
(A) Dehydration (B) Dehydrogenation
(C) Dehydro halogenation (D) Dehalogenation
2. Of the following, unsaturated hydrocarbons are – [IIT 1990]

(A) ethyne (B) cyclohexane (C) n–propane (D) ethene
3. 1-chlorobutane on reaction with alcoholic potash gives – [IIT 1991]

(A) 1–butene (B) 1–butanol (C) 2–butene (D) 2–butanol
4. The hybridisation of carbon atoms in C–C single bond of HCC–CH=CH2 is – [IIT 1991]
(A) sp3–sp3 (B) sp2–sp3 (C) sp–sp2 (D) sp2–sp2
ORGANIC CHEMISTRY
Cl
|
5. (CH 3 ) 2 C  CH 2CH 3 alc
. KOH
 ? [IIT 1992]
alc. KOH
6. C 6 H 5CH 2CHCH3 heat
 ? HBr
 ? [IIT 1993]
|
Br
7. C(C6H12), an optically active hydrocarbon which on catalytic hydrogenation gives an optically inactive
compound, C6H14. [IIT 1993]
8. Draw the stereochemical structure of the product in the following reactions. [IIT 1994]
2H
R–CC–R 
Lindlar catalyst
9. Write down the structures of the stereoisomers formed when cis–2–butene is reacted with bromine.
[IIT 1995]
10. An organic compound E(C5H8) on hydrogenation gives compound F(C5H12). Compound E on ozonolysis
gives formaldehyde and 2–ketopropanal. Deduce the structure of compound E. [IIT 1995]
11. Give the structures of the major organic products from 3–ethyl–2–pentene under each of the following
reaction conditions. [IIT 1996]
(a) HBr in the presence of peroxide (b) Br2/H2O
(c) Hg(OAc)2/H2O; NaBH4
12. An alkyl halide, (X) of formula C6H13Cl on treatment with potassium tertiary butoxide gives two isomeric
alkenes (Y) and (Z) (C6H12). Both alkenes on hydrogenation give 2, 3–dimethylbutane. Predict the
structures of (X), (Y) and (Z) [IIT 1996]
13. 3,3–Dimethylbutan–2–ol loses a molecule of water in the presence of concentrated sulphuric acid to
give tetramethylethylene as a major product. Suggest a suitable mechanism. [IIT 1996]
14. One mole of the compound A (molecular formula C8H12), incapable of showing stereoisomerism, reacts
with only one mole of H2 on hydrogenation over Pd. A undergoes ozonolysis to give a symmetrical
diketone B (C8H12O2). What are the structure of A and B? [IIT 1997]
15. Compound (A) C6H12 gives a positive test with bromine in carbon tetrachloride. Reaction of (A) with
alkaline KMnO4 yields only (B) which is the potassium salt of an acid. Write structure formulae and
IUPAC name of (A) and (B). [IIT 1997]
16. The central carbon–carbon bond in 1,3–butadiene is shorter than that of n–butane. Why?
17. Which of the following compounds will show geometrical isomerism? [IIT 1998]
(A) 2–butene (B) Propene (C) 1–phenylpropene (D) 2–methyl–2–butene
ORGANIC CHEMISTRY
18. The reaction of CH3– CH=CH OH with HBr gives: [JEE 1998]
(A) CH3CHBrCH2 OH (B) CH3CH2CHBr OH
(C) CH3CHBrCH2 Br (D) CH3CH2CHBr Br
19. Write the intermediate steps for each of the following reaction. [IIT 1998]

H
20. Write the intermediate steps for each of the following reaction [IIT 1998]
C6H5CH(OH)CCH  C6H5CHCHCHO
21. Give reasons for the following in one or two sentences. [JEE 1998]
"Acid catalysed dehydration of t-butanol is faster than that of n-butanol.
22. Benzyl chloride (C6H5CH2Cl) can be prepared from toluene by chlorination with:
(A) SO2Cl2 (B) SOCl2 (C) Cl2 (D) NaOCl [IIT 1998]
23. Carry out the following transformation in not more than three steps. [IIT 1999]
O
||
CH3–CH2–CC–H  CH 3  CH 2  CH 2  C  CH 3
24. Discuss the hybridisation of carbon atoms in allene (C3H4) and show the –orbital overlaps.
[IIT 1999]
25. Complete the following – [IIT 1999]
1 2 3

 
 

26. Complete the following – [IIT 1999]
4 5 6

 
 

ORGANIC CHEMISTRY
27. In the compound CH2=CH–CH2–CH2–CCH, the C2–C3 bond is of the type – [IIT 1999]
(A) sp–sp2 (B) sp3–sp3 (C) sp–sp3 (D) sp2–sp3
28. What would be the major product in each of the following reactions? [IIT 2000]
CH 3
| C2 H 5OH H
2
(i) CH 3
 C  CH 2 Br   (ii) 
 Lindlar 's Catalyst
|
CH 3
29. CH2=CH– is more basic than HCC– [IIT 2000]
30. Propyne and propene can be distinguished by – [IIT 2000]

(A) conc. H2SO4 (B) Br2 in CCl4 (C) dil. KMnO4 (D) AgNO3 in ammonia
31. Which one of the following alkenes will react fastest with H2 under catalytic hydrogenation condition –
[IIT 2000]
(A) (B) (C) (D)
32. In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti–Markovnikov
addition to alkene because – [IIT 2001]
(A) both are highly ionic
(B) one is oxidising and the other is reducing
(C) one of the step is endothermic in both the cases
(D) All the steps are exothermic in both cases
33. The reaction of propene with HOCl proceeds via the addition of – [IIT 2001]
(A) H+ in first step (B) Cl+ in first step (C) OH– in first step (D) Cl+ and OH– in single step
34.
Hydrogenation of the above compound in the presence of poisoned paladium catalyst gives –
(A) An optically active compound (B) An optically inactive compound [IIT 2001]
(C) A racemic mixture (D) A diastereomeric mixture
35. On reaction with 4N alcoholic KOH at 175 °C 1–pentyne is slowly converted into equilibrium mixture
of 1.3% 1–pentyne (A), 95.2% 2–pentyne (B) and 3.5% 1,2–pentadiene (C). Give the suitable
mechanism of formation of A, B and C with all intermediates. [IIT 2001]
ORGANIC CHEMISTRY
36. A biologically active compound, Bombykol (C16H30O) is obtained from a natural source. The structure
of the compound is determined by the following reactions.
(a) On hydrogenation, Bombykol gives a compound A, C16H34O, which reacts with acetic anhydride to
give an ester.
(b) Bombykol also reacts with acetic anhydride to give another ester, which on oxidative ozonolysis
(O3/H2O2) gives a mixture of butanoic acid, oxalic acid and 10-acetoxy decanoic acid.
Determine the number of double bonds in Bombykol. Write the structures of compound A and Bombykol.
How many geometrical isomers are possible for Bombykol? [IIT 2002]
37. Identify X, Y and Z in the following synthetic scheme and write their structures. Is the compound Z
optically active? Justify your answer. [IIT 2002]
(i ) NaNH
H / Pd  BaSO
CH3CH2CC–H   2  X 2   4  Y alkaline KMnO
   4  Z
(ii ) CH3CH 2 Br
38. Consider the following reactions – [IIT 2002]
H 3C  CH  CH  CH3 + ‘X’ + HBr

| |
D CH3
Identify the structure of the major product ‘X’
• •
(A) H 3C  CH  CH  C H 2 (B) H 3C  CH  C CH 3
| | | |
D CH 3 D CH 3
• •
(C) H 3C  C CH  CH 3 (D) H 3C  C H  CH  CH 3
| | |
D CH 3 CH 2
39. The nodal plane in the –bond of ethene is located in – [IIT ‘2002]
(A) the molecular plane
(B) a plane parallel to the molecular plane
(C) a plane perpendicular to the molecular plane which contains the carbon–carbon –bond at right angle
(D) a plane perpendicular to the molecular plane which contains the carbon–carbon –bond
40. Identify a reagent from the following list which can easily distinguish between 1–butyne and 2-butyne-
[IIT 2002]
(A) bromine, CCl4 (B) H2, Lindlar catalyst
(C) dilute H2SO4, HgSO4 (D) ammonical Cu2Cl2 solution
ORGANIC CHEMISTRY
HgSO
41. 4  A
C6H5–CC–CH3   [IIT 2003]
H 2SO 4
(A) (B)
(C) C 6 H 5  C  CHCH 3 (D) C 6 H 5  CH  C  CH 3

| |
OH OH

H x Br
42.  H 2O ( mixture) 2 5 compounds of molecular formula C4H8Br2

Number of compounds in X will be: [IIT 2003]

(A) 2 (B) 3 (C) 4 (D) 5
43. 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
44. Cyclohexene is best prepared from cyclohexanol by which of the following : [IIT 2005]
(A) conc. H3PO4 (B) conc. HCl/ZnCl2 (C) conc. HCl (D) conc. HBr
45. When Phenyl Magnesium Bromide reacts with tert. butanol, which of the following is formed?
(A) Tert. butyl methyl ether (B) Benzene [IIT 2005]
(C) Tert. butyl benzene (D) Phenol
46. 1–bromo–3–chlorocyclobutane when treated with two equivalents of Na, in the presence of ether which
of the following will be formed? [IIT 2005]
(A) (B) (C) (D)
47. If after complete ozonolysis of one mole of monomer of natural polymer gives two moles of CH2O and
CH 3
|
one mole of O  C  CH  O . Identify the monomer and draw the all-cis structure of natural polymer..
[IIT 2005]
 3 (i) O
48. H ,
X    Y.
(ii ) Zn / CH COOH 3
Identify X and Y. [IIT 2005]
ORGANIC CHEMISTRY
49. CH3–CH=CH2 + NOCl  P [IIT 2006]
Identify the adduct.
CH 3  CH  CH 2 CH 3  CH  CH 2
(A) | | (B) | |
Cl NO NO Cl
NO
| CH 2  CH 2  CH 2
CH 3  CH 2  CH
(C) | (D) | |
NO Cl
Cl
50. The number of stereoisomers obtained by bromination of trans-2-butene is [IIT 2007]

(A) 1 (B) 2 (C) 3 (D) 4
51. The number of structural isomers for C6H14 is [IIT 2007]

(A) 3 (B) 4 (C) 5 (D) 6
52. The reagent(s) for the following conversion, [IIT 2007]
?

 H H is / are
(A) alcoholic KOH (B) alcoholic KOH followed by NaNH2

(C) aqueous KOH followed by NaNH2 (D) Zn / CH3OH
53. In the following carbocation, H/ CH3 that is most likely to migrate to the positively charged carbon is
H H
1 2 + 4 5
H3C—C—C—C—CH3
3 [JEE 2009]
HO H CH3
(A) CH3 at C-4 (B) H at C-4 (C) CH3 at C-2 (D) H at C-2
54. The synthesis of 3-octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an
alkyne. The bromoalkane and alkyne respectively are [IIT 2010]
(A) BrCH2CH2CH2CH2CH3 and CH3CH2CCH
(B) BrCH2CH2CH3 and CH3CH2CH2CCH
(C) BrCH2CH2CH2CH2CH3 and CH3CCH
(D) BrCH2CH2CH2CH3 and CH3CH2CCH
ORGANIC CHEMISTRY
55. The number of optically active products obtained from the complete ozonolysis of the given compound
is [JEE 2012]
CH3 H
CH3–CH=CH–C–CH=CH–C–CH=CH–CH3
H CH3
(A) 0 (B) 1 (C) 2 (D) 4
56 In allene (C3H4), the type(s) of hybridisation of the carbon atoms is (are) [JEE 2012]
(A) sp and sp 3 (B) sp and sp 2 (C) only sp2 2
(D) sp and sp3
57. Isomers of hexane, based on their brancing, can be divided into three distinct classes as shown in the
figure. [JEE Advance 2014]
I and II and III
The correct order of their boiling point is

(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II
58. In the following reaction, the major product is : [JEE Advance 2015]
CH 3
1 equivalent HBr
CH2
H2C
CH3 CH3
CH3
(A) H C (B)
2 H3C
Br Br
CH 3 CH 3
(C) (D)
H2C Br H3C Br
59 Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is(are)

[JEE Advance 2015]
H H
Br Br
(A) H C (B)
3
CH 3 H2C CH3
H Br
H2C Br H
(C) CH3 (D)
H2C CH3
CH 3
ORGANIC CHEMISTRY
60. The number of hydroxyl group(s) in Q is [JEE Advance 2015]
+
H aqueous dilute KMnO4(excess)
H P Q
heat 0°C
HO
H 3C CH3
Paragraph for question nos. 61 & 62

In the following reactions : [JEE Advance 2015]
C8 H 6 Pd
BaSO 4
 C8 H 8 i
. B2H6
 X
H2 ii . H 2O 2 , NaOH , H 2O
 H 2O
 HgSO 4 , H 2SO 4
C8 H8O i
. EtMgBr , H 2O
      Y
ii . H  , Heat
61. Compound X is
O OH
OH
CH3 CH3 CHO
(A) (B) (C) (D)
62. The major compound Y is
(A) CH 3 (B) CH 3
CH2 CH3
CH3
(C) (D) CH3
63. In the following monobromination reaction, the number of possible chiral products is
[JEE Advance 2016]
CH2CH2CH3
H Br
CH3 Br (1.0 mole )
2 300
º C
(1.0 mole)
(enantiomerically pure)
ORGANIC CHEMISTRY
64. The correct statement(s) for the following addition reactions is(are) [JEE Advance 2017]
H3C H
(i) Br / CHCl3
2   M and N
H CH3
H3C CH3
(ii) Br / CHCl3
2   O and P
H H
(A) O and P are identical molecules
(B) Bromination proceeds through trans-addition in both the reactions
(C) (M and O) and (N and P) are two pairs of enantiomers
(D) (M and O) and (N and P) are two pairs of diastereomers
65. Compounds P and R upon ozonolysis produce Q and S, respectively. The molecular formula of Q and
S is C8H8O. Q undergoes Cannizzaro reaction but not haloform reaction, whereas S undergoes haloform
reaction but not Cannizzaro reaction. [JEE Advance 2017]
(i ) O3 / CH 2Cl 2
(i) P     Q
(ii ) Zn / H O
2 ( C8H8O )
(i ) O3 / CH 2Cl 2
(ii) R     S
(ii ) Zn / H O
2 ( C8 H8O )
The option(s) with suitable combination of P and R, respectively, is(are)
(A) H3C and

CH3
H3C
CH3 CH3
and
(B)
CH3
H3C
H3C CH3
CH3 CH3
and
(C)
CH3
CH3
(D) H3C and H3C

CH3
ORGANIC CHEMISTRY
66. Total number of hydroxyl groups present in a molecule of the major product P is_________
[JEE Adv. 2019]
(i) H2,Pd-BaSO4, quinoline

P
(ii) dil. KMnO4 (excess), 273 K
67. In the reaction scheme shown below, Q, R and S are the major products. [JEE Adv. 2020]
The correct structure of
(A) S is (B) Q is
(C) R is (D) S is
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. B 2. A 3. B 4. B 5. C 6. B 7. D
8. C 9. A 10. A 11. C 12. A 13. A 14. C
15. C 16. B 17. A 18. D 19. D 20. C 21. D
22. C 23. C 24. A 25. C 26. A 27. A 28. C
29. C 30. C 31. B 32. D 33. D 34. C 35. C
36. A 37. 8 38. A 39. C 40. A 41. A 42. C
43. C 44. C
[JEE-ADVANCED]
1. C 2. AD 3. A 4. C 5. CH 3  C  CH  CH3
|
CH 3
alc. KOH
6.   HBr

heat
H
|
7. CH 3  CH 2  C  CH  CH 2 8.
|
CH 3
(C6 H12 )
CH 2 CH 2
|| ||
9. 10. (E) CH 3  C  CH
Br OH
| |
11. (a) (CH3–CH2)2 CH  CH  CH 3 ; (b) (CH3–CH2)2 C  CH  CH 3 ; (c) (C2H5)3C–OH
|
Br
CH 3 CH 3 CH 3 CH 3 CH 3 CH 3
| | | | | |
12. CH 3  C  CH  CH 3 ; (Y) CH 2  C  CH  CH 3 ; (Z) CH 3  C  C  CH 3
|
Cl
ORGANIC CHEMISTRY
C
C C | 
conc. H 2SO4
13. C–C–C–C C–C–C–C CCCC
–H2O
 |
C OH + C OH2 C
H
1,2-methyl shift
H  
C  C  C  C  C  C  C  C
| | | |
C C C C
14. (A) (B)
15. (A) CH3–CH2–CH=CH–CH2–CH3 (B) CH3CH2COOK

16. Presence of partial double bond character due to resonance.
17. AC 18. B
+ +
19. H –H

H O
20. C6H5CH(OH)CºCH 
3


OH 
C6H5CH=CHCHO C6H5CH=C= CH  C6H5CH=C= C H
|
OH
21. Acid catalysed dehydration proceeds via carbocation intermediate. ALso, greater the stability of reactive
intermediate, faster the reaction:
CH 3 CH 3
|  |
H
CH 3  C  OH  CH 3  C 
 CH 3
|  H 2O
3 highly stable
CH 3
t  butanol
n-butanol forms less stable (1°) carbocation.

22. AC
ORGANIC CHEMISTRY
23. (1) NaNH2, (2) Me–I, (3) HgSO4 dil H2SO4

24. H2C = C = CH2
P4–P4
P3–P3
25. 1 ozonolysis ; 2 LiAlH4 ; 3 H2SO4

26. (4)  HO–Cl ; (5)  CH3MgCl ; (6) H2O/H+
CH3
|
27. D 28. (i) CH 3  C  CH  CH3 (ii)
29. higher electronegativity of sp carbon

30. D 31. A 32. C 33. B 34. B
alc.KOH 
35. H3C – CH2 – CH – C CH H3C – CH2 – CH – C CH
– H 2O
H
H2O 
H3C – CH2 – CH = C CH2 H3C – CH2 – CH = C CH
– H2O alc.KOH
 
H3C – CH2 – C = C CH2 H3C – CH2 – C  C –CH2
H 2O
H3C – CH2 – C  C –CH3
36. Bombykol :- HO–C–C–C–C–C–C–C–C–C–C=C–C=C–C–C–C

(A) :- 4 geometrical isomers are possible
37. (X)  Et–CC–Et (Y)  (Z)  Z is meso so optically inactive.
38. B 39. A 40. D 41. A 42. B 43. B 44. A

45. B 46. D
ORGANIC CHEMISTRY
CH3
|
47. (a) CH 2  C  CH  CH 2 (b)
O
||
48. (X) , (Y) CH 3  C  (CH 2 ) 4  CH  O
49. A 50. A 51. C 52. B 53. D 54. D 55. A

56. B 57. B 58. D 59. BD 60. 4 61. C 62. D
63. 5 64. BD 65. AB 66. 6 67. BD
ORGANIC CHEMISTRY
HALOGEN DERIVATIVE
[JEE-MAIN / AIEEE]
H2O
1. The reaction : (CH3)C – Br  (CH3)3 – C – OH [AIEEE-2002]
(A) elimination reaction (B) substitution reaction
(C) free radical reaction (D) displacement reaction
2. The correct order of the thermal stability of hydrogen halides (H – X) is [AIEEE-2005]

(A) HI > HBr > HCl > HF (B) HF > HCl > HBr > HI
(C) HCl < HF > HBr < HI (D) HI > HCl < HF < HBr
3. Tertiary alkyl halides are practically inert to substitution by SN2 mechanism because of
[AIEEE-2005]
(A) insolubility (B) instability (C) inductive effect (D) steric hindrance
4. Elimination of bromine from 2-bromobutane results in the formation of- [AIEEE-2005]

(A) equimolar mixture of 1 and 2-butene (B) predominantly 2-butene
(C) predominantly 1-butene (D) predominantly 2-butyne
5. CH3Br + Nu–  CH3–Nu + Br– [AIEEE-2006]

The decreasing order of the rate of the above reaction with nucleophiles (Nu–) A to D is
[Nu– = (A) PhO–, (B) AcO–, (C) HO–, (D) CH3O–]
(A) D > C > A > B (B) D > C > B > A (C) A > B > C > D (D) B > D > C > A
6. The structure of the major product formed in the following reaction [AIEEE-2006]
NaCN
 

DMF
is
Cl CN Cl CN
(A) (B) (C) (D)
NC
CN I CN I
7. Reaction of trans-2-phenyl-1-bromocyclopentane on reaction with alcoholic KOH produces

(A) 4-phenylcyclopentene (B) 2-phenylcyclopentene [AIEEE-2006]
(C) 1-phenylcyclopentene (D) 3-phenylcyclopentene
8. Which of the following is the correct order of decreasing SN2 reactivity? [AIEEE-2007]
(A) RCH2X > R3CX > R2CHX (B) RCH2X > R2CHX > R3CX
(C) R3CX > R2CHX > RCH2X (D) R2CHX > R3CX > RCH2X
ORGANIC CHEMISTRY
9. The organic chloro compound, which shows complete stereochemical inversion during a SN2 reaction,
is [AIEEE-2008]
(A) (C2H5)2CHCl (B) (CH3)3CCl (C) (CH3)2CHCl (D) CH3Cl
10. Which of the following on heating with aqueous KOH, produces acetaldehyde ? [AIEEE-2009]
(A) CH2 Cl CH2 Cl (B) CH3 CHCl2 (C) CH3 COCl (D) CH3 CH2 Cl
11. From amongst the following alcohols the one that would react fastest with conc. HCl and anhydrous
ZnCl2, is [AIEEE-2010]
(A) 2-Methylpropanol (B) 1-Butanol (C) 2-Butanol (D) 2-Methylpropan-2-ol
12. Consider the following bromides : [AIEEE-2010]
Me Me
Me Br Me
Br Br
A B C
The correct order of SN1 reactivity is

(A) C > B > A (B) A > B > C (C) B > C > A (D) B > A > C
13. The main product of the following reaction is [AIEEE-2010]

conc .H2SO4
C6H5CH2CH(OH)CH(CH3)2     ?

C6 H5 CH(CH3)2
(A) C=C (B) H5C6CH2CH2
C = CH2
H H H3C
H5C6 H
(C) C=C (D) C6H5CH2 CH3
CH(CH3)2 C=C
H
H CH3
14. An unknown alcohol is treated with the “Lucas reagent” to determine whether the alcohol is primary,
secondary or tertiary. Which alcohol reacts fastest and by what mechanism : [JEE-Main-2013]
(A) tertiary alcohol by SN2 (B) secondary alcohol by SN1
(C) tertiary alcohol by SN1 (D) secondary alcohol by SN2
15. A solution of (–) – 1 – chloro – 1 – phenylethane is toluene racemises slowly in the presence of a small
amount of SbCl5, due to the formation of : [JEE-Main-2013]
(A) free radical (B) carbanion (C) carbene (D) carbocation
16. 2-chloro-2methylpentane on reaction with sodium methoxide in methanol yields :
CH3
(a) C2H5CH2C – OCH3 (b) C2H5CH2C = CH2 (c) C2H5CH = C – CH3 [JEE-Main-2016]
CH3 CH3 CH3
(A) All of these (B) (a) and (c) (C) (c) only (D) (a) and (b)
ORGANIC CHEMISTRY
17. The reaction of propene with HOCl (Cl2 + H2O) proceeds through the intermediate :
(A) CH3 – CH+ – CH2 – OH (B) CH3 – CH+ – CH2 – Cl [JEE-Mains-2016]
(C) CH3 – CH(OH) – CH2+ (D) CH3 – CHCl – CH2+
18. Which one of the following reagents is not suitable for the elimination reaction ?
[JEE-Mains-2016 (online)]
Br
(A) NaI (B) NaOH/H2O-EtOH (C) NaOH/H2O (D) NaOEt/EtOH
19. Bromination of cyclohexene under conditions given below yields : [JEE-Mains-2016 (online)]
Br2 /h
Br
Br
Br Br
(A) (B) (C) (D)

Br Br
Br
20. The major product of the following reaction is : [JEE-Mains Online -2017]
CH3
C6H5CH2 – C – CH2 – CH3 C2H5ONa
C2H5OH
Br
(A) C6H5CH = C – CH2CH 3 (B) C6H5CH2 – C = CH2

CH3 CH2CH3
CH3
(C) C6H5CH2 – C – CH2CH3 (D) C6H5CH 2 – C = CH CH3
OC2H5 CH3
CH3CH CH2CHCH2CH3 KOH, CH3OH
heat
Br Br
(A) CH2 = CHCH = CHCH2CH3 (B) CH3CH = CH – CH = CHCH3
(C) CH2 = CHCH2CH = CHCH3 (D) CH3CH = C = CHCH2CH3
OH
1. K2CO3
2. CH3I(1. eq.)
OH
ORGANIC CHEMISTRY
OCH3 OH OCH3
O
(A) (B) (C) (D)
OCH3 OH
23. The IUPAC name of the following compound is : [JEE-Mains Online -2017]
(A) 2-Ethyl-1,1-dimethylcyclohexane (B) 1-Ethyl-2,2-dimethylcyclohexane

(C) 1,1-Dimethyl-2-ethylcyclohexane (D) 2,2-Dimethyl-1-ethylcyclohexane
24. A mixture containing the following four compounds is extracted with 1M HCl. The compound that goes
to aqueous layer is : [JEE-Mains Online -2017]
H O
S N O
(I) (II) (III) (IV)
(A) (IV) (B) (II) (C) (I) (D) (III)

25. Which of the following compounds is most reactive to an aqueous solution of sodium carbonate?
[JEE-Mains Online -2017]
(A) (B) (C) (D)
26. In the following structure, the double bonds are marked as I, II, III and IV
II
III
I IV
Geometrical isomerism is not possible at site (s) : [JEE-Mains Online -2017]

(A) III (B) I (C) I and III (D) III and IV
Br2 / h
Br
Br Br
(A) (B) (C) (D)
Br
Br
ORGANIC CHEMISTRY
28. The increasing order of the boiling points for the following compounds is :
(I) C2H5OH (II) C2H5Cl (III) C2H5CH3 (IV) C2H5OCH3 [JEE-Mains Online -2017]
(A) (III) < (IV) < (II) < (I) (B) (IV) < (III) < (I) < (II)
(C) (II) < (III) < (IV) < (I) (D) (III) < (II) < (I) < (IV)
29. Which of the following compounds will show highest dipole moment? [JEE-Mains Online -2017]
O O
(I) O (II) (III) O (IV)
O
(A) (I) (B) (II) (C) (III) (D) (IV)
30. Among the following compounds, the increasing order of their basic strength is :
NH2 CH3
(I) (II) (III) N (IV)
N NH2
H
(A) (I) < (II) < (IV) < (III) (B) (I) < (II) < (III) < (IV)
(C) (II) < (I) < (IV) < (III) (D) (II) < (I) < (III) < (IV)
31. Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to
decolourize the colour of bromine? [JEE-Mains-2017]
O
O C6H5 O
(A) (B) (C) (D)
Br Br Br
Br
32. The increasing order of the reactivity of the following halides for the SN1 reaction is :
[JEE-Mains-2017]
(I) CH3CHCH2CH3 (II) CH3CH2CH2Cl (III) p – H3CO – C6H4 – CH2Cl
Cl
(A) (II) < (III) < (I) (B) (III) < (II) < (I) (C) (II) < (I) < (III) (D) (I) < (III) < (II)
33. The major product obtained in the following reaction is [JEE-Mains-2017]
Br
H t
BuOK
C6H5

C6H5
(+)
(A) (–)C6H5CH(OtBu)CH2C6H5 (B) (±)C6H5CH(OtBu)CH2C6H5

(C) C6H5CH = CHC6H5 (D) (+)C6H5CH(OtBu)CH2C6H5
ORGANIC CHEMISTRY
34. Which of the following molecules is least resonance stabilized? [JEE-Mains-2017]
(A) (B) (C) (D) N

O O
35. 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-Mains-2017]
(A) Four (B) Six (C) Zero (D) Two
36. The major product formed in the following reaction is : [JEE-Mains-2018]
O HI
Heat
O
I OH I OH
(A) (B) (C) (D)
OH OH I I
37. The major product of the following reaction is : [JEE-Mains-2018]

Br NaOMe
MeOH
OMe OMe
(A) (B) (C) (D)
(i) KOH (alc.)
(2) Free radical
Cl Cl polymerisation
CH3
n
n
(A) (B)
Cl
OH
CH3
n n
(C) (D)
OH
Cl
ORGANIC CHEMISTRY
39. Increasing order of reactivity of the following compunds for SN1 substitution is :
CH3
CH2 – Cl Cl Cl
H3C Cl
CH3
H3CO
(i) (ii) (iii) (iv)
(A) (ii) < (i) < (iv) < (iii) (B) (ii) < (iii) < (i) < (iv)
(C) (i) < (ii) < (iv) < (iii) (D) (ii) < (iii) < (iv) < (i)
40. Heating of 2-chloro-1 phenylbutane with EtOK/EtOH gives X as the major product. Reaction of X with
Hg (OAc)2/H2O followed by NaBH4 gives Y as the major product . Y is :
OH OH
(A) Ph (B) Ph (C) Ph (D) Ph

OH
Br
KOH alc (excess)

Ph
Br
(A) (B) (C) (D)

Ph Ph
Ph Ph
42. Which of the following compounds will show retention in configuration on nucleophile substitution by
ion ? [JEE-Mains Online -2020]
(A) (B) (C) (D)
43. The major aromatic product C in the following reaction sequence will be :
(A) (B) (C) (D)
ORGANIC CHEMISTRY
44. The major product obtained from E2-elimination of 3-bromo-2- fluoropentane is
CH3 CH3
| |
(A) CH3—CHz—C——CH—CH3 (B) CH3CH2—CH—CH—
— CH3
CH3
|
(C) CH 3—CH —
— CH—CH—CH 3 —C—F
(D) CH3CH2CH —
|
CH3
45. The mechanism of SN1 reaction is given as: [JEE-Mains Online -2020]
R—X R  X R|| X Y R — Y + X
Ion pair Solvent
Separated ion
pair
A student writes general characteristics based on the given mechanism as :

(a) The reaction is favoured by weak nucleophiles.
(b) R would be easily formed if the substituents are bulky
(c) The reaction is accompanied by racemization
(d) The reaction is favoured by non-polar solvents.
Which observations are correct ?
(A) (b) and (d) (B) (a) and (c) (C) (a) and (b) (D) (a), (b) and (c)
46. The decreasing order of reactivity of the following compounds towards nucleophilic substitution (SN2)
is : [JEE-Mains Online -2020]
(A) (II) > (III) > (I) > (IV) (B) (II) > (III) > (IV) > (I)
(C) (III) > (II) > (IV) > (I) (D) (IV) > (II) > (III) >(I)
47. When neopentyl alcohol is heated with an acid, it slowly converted into an 85 : 15 mixture of alkenes A
and B, respectively. What are these alkenes ? [JEE-Mains Online -2020]
(A) (B)
(C) (D)
ORGANIC CHEMISTRY
48. Consider the reaction sequence given below : [JEE-Mains Online -2020]
Which of the following statements is true:

(A) Changing the concentration of base will have no effect on reaction (A)
(B) Doubling the concentration of base will double the rate of both the reactions
(C) Changing the concentration of base will have no effect on reaction (B)
(D) OH will have no effect on reaction (B)
49. The major product [B] in the following reaction is : [JEE-Mains Online -2020]
(A) CH2 = CH2 (B)
(C) (D) CH3 – CH2CH = CH – CH3
50. The major product [R] in the following sequence of reaction is : [JEE-Mains Online -2020]
H3C
H3C
(A) C = CH– CH3 (B) CH – CH= CH2
(CH3)2CH (CH3)2CH
H2C H3C
(C) C – CH2– CH3 (D) C = C(CH3)2
CH(CH3)2 H3CCH2
51. The major product in the following reaction is : [JEE-Mains Online -2020]
CH3CH = CHCH(CH3)2 HBr
(A) CH3CH(Br)CH2CH(CH3)2 (B) Br(CH2)3CH(CH3)2

(C) CH3CH2CH2C(Br)(CH3)2 (D) CH3CH2CH(Br)CH(CH3)2
ORGANIC CHEMISTRY
OH CH2CH3
H2SO4
CHCH3 CH2CH3 CH2CH 3 CH = CH2
(A) (B) (C) (D)

O O O O
53. The major products of the following reaction are : [JEE-Mains Online -2020]
CH3 CH3
(A) + CH3CHO (B) + HCHO

H3C O H3C CHO
CH3 CH3
(C) + CH3COOH (D) + HCOOH

H3C H3C COOH
O
54. The major product in the following reaction is: [JEE-Mains Online -2020]
(A) (B) (C) (D)
[JEE-ADVANCED]
1. Chloroform is stored in dark coloured bottles. Explain in not more than two sentences. [JEE 1980]
2. The compound which reacts fastest with Lucas reagent at room temperature is [JEE 1981]
(A) butan-2-ol (B) butan-1-ol
(C) 2-methyl propan-1-ol (D) 2-methyl propan-2-ol
3. The halogen which is most reactive in the halogenation of alkanes under sunlight is ______.
[JEE 1981]
ORGANIC CHEMISTRY
4. Carbon tetrachloride burns in air to give phosgene. [IIT 1983]
5. Diethyl ether on heating with concentration HI gives two moles of [JEE 1983]
(A) ethanol (B) iodoform (C) ethyl iodide (D) methyl iodide
6. Carbon tetrachloride is inflammable. [IIT 1985]
7. Iodide is better nucleophile than bromide. [IIT 1985]
8. Write down the main product of the following reaction: [JEE 1985]
Ethanol I
2 / NaOH

9. HBr reacts fastest with [JEE 1986]

(A) 2-methyl propan-2-ol (B) propan-1-ol
(C) propan-2-ol (D) 2-methyl propan-1-ol
10. The reaction condition leading to the best yield of C2H5Cl are [JEE 1986]
dark
(A) C2H6 (excess) + Cl2 UV
 light
 (B) C2H6 + Cl2 (excess)  
room temp .
(C) C2H6 + Cl2 (excess) UV

 light
 (D) C2H6 + Cl2 UV
 light


(C) Propan-2-ol (D) 2-methyl propan-1-ol
12. How may be the following transformation be carried out (in not more than six steps)? [JEE 1986]
"Ethyl alcohol to vinyl acetate".
13. n-propyl bromide on treatment with ethanolic potassium hydroxide produces. [IIT 1987]
(A) Propane (B) Propene (C) Propyne (D) Propanol
14. The reaction of vinyl chloride with hydrogen iodide to give 1-chloro-1-iodo ethane is an example of
anti-Markownikoff's rule. [JEE 1989]
15. During SN1 reactions, the leaving group leaves the molecule before the incoming group is attached to the
molecule. [IIT 1990]
16. Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to
(A) The formation of less stable carbonium ion
(B) Resonance stabilization
(C) The inductive effect
(D) sp2 hybridised carbon attached to the halogen [IIT 1990]
17. The compounds used as refrigerant are [JEE 1990]
(A) NH3 (B) CCl4 (C) CF4 (D) CF2Cl2
(E) CH2F2
18. 1-Chlorobutane on reaction with alcoholic potash gives:

(A) 1-butene (B) 1-butanol (C) 2-butene (D) 2-butanol [ITT 1991]
ORGANIC CHEMISTRY
19. The products of reaction of alcoholic AgNO2 with ethyl bromide are [IIT 1991]
(A) Ethane (B) Ethyl nitrite (C) Nitroethane (D) Ethyl alcohol
20. Fill in the blanks:
(a) Butan nitrile can be prepared by heating _____with alcohalic KCN. [IIT 1992]
(b) Amongst three isomers of nitrophenol, the one that is least soluble in water is_____ [IIT 1992]
21. Arrange the following in order of their
(i) Increasing basicity
H2O, OH¯, CH3OH, CH3O¯
(ii) Increasing reactivity in nucleophilic substitution reactions
CH3F, CH3I, CH3Bt, CH3Cl [IIT 1992]
22. Write the structures of the major organic product expected from each of the following rreactions:
[IIT 1992]
CH3
(i) H3C CH2CH3 Alc

. KOH

Cl
aq.alkali
(ii) CH3CH2CHCl2   
23. Photobromination of 2-methylpropane gives a mixture of 1-bromo-2-methyl propane and

2-bromo-2-methyl propane in the ratio 9 : 1. [JEE 1993]
24. Identify the major product in the following reaction. [IIT 1993]
H
Alc.KOH
C6H5—CH 2 CH3   ? HBr
 ?

Br
25. Identify the major product in the following reactions : [IIT 1993]
Cl
| alcoholic
(i) C 6 H 5  CH 2  CH  CH 3    ? HBr
 ?
KOH 
(ii) C6H5COOH + CH3MgI  ? + ?
26. Aryl halides are less reactive than alkyl halides towards nucleophilic reagents. Give reason.
[IIT 1994]
27. Draw the stereochemical structure of product in the following reaction. [IIT 1994]
CH3
Br H NaOH

SN 2
C2H5
ORGANIC CHEMISTRY
28. In the following reactions, identify the compounds A,B,C and D. [JEE 1994]
(i) PCl5 + SO2  A + B
(ii) A + CH3COOH  C + SO2 + HCl
(iii) 2C + (CH3)2Cd  2D + CdCl2
29. Optically active 2-iodobutane on treatment with NaI in acetone gives a product which does not show
optical activity. Explain briefly. [ITT 1995]
30. Write down the structure of the stereoisomers formed when cis-2-butene is reacted with bromine.
[JEE 1995]
31. 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
32. An alkyl halide X of formula C6H13Cl on treatment with potassium tertiary butoxide gives two isomeric
alkenes Y and Z (C6H12). Both alkenes on hydrogenation give 2,3–dimethylbutane. Predict the structures
of X, Y and Z. [IIT 1996]
33. Predict the structure of the intermediates/products in the following reaction sequence – [IIT 1996]
NaI

 C
Acetone
34. A compound D (C8H8O) upon treatment with alkaline solution of iodine gives a yellow precipitate. The
filtrate on acidification gives a white solid E (C7H6O2). Write the structures of D, E and explain the
formation of E. [JEE 1996]
35. Which of the following is the correct method for synthesising methyl-t-butyl ether and why?
(CH3)3 CBr + NaOMe 
or CH3Br + NaO-t-Bu  [IIT 1997]
36. Statement-1 : Addtition of Br2 to 1-butene gives two optical isomers. [JEE 1998]
Statement-2 : The product contains one asymmetric carbon.
(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.
37. (CH3)2CHOCH3 HI

( excess
 )  A + B Write structures of A and B. [IIT 1998]
Heat
ORGANIC CHEMISTRY
38. Complete the following reaction with appropriate structures of products/reagents. [IIT 1998]
Br2 (i ) NaNH ( 3 equi.)

 (A)   2  
  (B)
( II) CH3I
39. A solution of (+) 2-chloro-2-phenylethane in toluene racemises slowly in the presence of small amount
of SbCl5, due to the formation of [IIT 1999]
(A) carbanion (B) carbene (C) free radical (D) carbocation
40. Explain briefly the formation of products giving the structures of the intermediates. [JEE 1999]
(i) HCl
 + + etc.
(ii) HCl
 only. Also explain the non-formation
of cyclic product in the reaction.

41. The order of reactivity of the following alkyl halides for a SN2 reaction is: [IIT 2000]
(A) RF > RC > 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
42. Which of the following has the highest nucleophilicity?
(A) F¯ (B) OH¯ (C) CH3¯ (D) NH2¯ [IIT 2000]
43. Statement-1 : 1-butene on reaction with HBr in the presence of a peroxide produces 1-bromobutane.
Statement-2 : It involves the formation of a primary radical. [JEE 2000]
44. What would be major product? [IIT 2000]
CH 3
|
CH 3  C  CH 2 Br C
2 H 5OH
 ?
| 
CH 3
45. An SN2 reaction at an asymmetric carbon of a compound always gives.

(A) an enantiomer of the substance (B) a product with opposite optical rotation
(C) a mixture of diastereomers (D) a single stereoisomer [IIT 2001]
46. The compound that will react most readily with NaOH to form methanol is
(A) (CH3)4N+ I ¯ (B) CH3OCH3 (C) (CH3)3S+ I ¯ (D) (CH3)3Cl [IIT 2001]
ORGANIC CHEMISTRY
47. Statement-1 : Addition of bromine to trans-2-butene yields meso-2,3-dibromo butane.
Statement-2 : Bromine addition to an alkene is an electrophilic addition. [JEE 2001]
48. Consider the following reaction. [JEE 2002]

H 3C  CH  CH  CH 3  Br 
 ' X ' HBr
| |
D CH 3
Identify the structure of the major product X.
 
(A) H 3C  CH  CH  CH 2 (B) H 3C  CH  C  CH 3
| | | |
D CH 3 D CH 3
 
(C) H 3C  C — CH  CH 3 (D) H 3C  CH  CH  CH 3
| | |
D CH 3 CH 3
49. Identify the set of reagents / reaction conditions 'X' and 'Y' in the following set of transformation:
X
CH3 – CH2 – CH2Br  Y
Product  CH 3  CH  CH 3
|
Br
(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 [IIT 2002]
50. Identify X, Y and Z in the following synthetic scheme and write their structures
(i ) NaNH 2
CH3CH2C  CH     X
(ii ) CH CH Br
[IIT 2002]
3 2
51. The product of following reaction is [IIT 2003]
OH
+ C2H5 I C
2 H 5O ¯( excess )
  
anhy . C 2 H5OH
(A) C6H5OC2H5 (B) C2H5OC2H5 (C) C6H5OC6H5 (D) C6H5I

52. How many chiral compounds are possible on monochlorination of 2-methyl butane? [JEE 2004]
(A) 2 (B) 4 (C) 6 (D) 8
ORGANIC CHEMISTRY
53. The following compound on hydrolysis in aqueous acetone will give: [IIT 2005]
CH3 H CH3
MeO NO2
H Cl CH3
CH3 H CH3
(K) MeO NO2
H OH CH3
CH3 H CH3
(L) MeO NO2
OH H CH3
CH3 H CH3
(M) MeO NO2
H CH3 OH
It mainly gives
(A) K and L (B) Only K (C) L and M (D) Only M
54. Match the following: [IIT 2006]
Column I Column II
(A) CH3–CHBr–CD3 on treatment with alc. KOH gives (P) E1 reaction
CH2=CH-CD3 as a major product.
(B) Ph – CHBr - CH3 reacts faster than Ph-CHBr-CD3. (Q) E2 reaction
(C) Ph-CD2-CH2Br on treatment with C2H5OD/C2H5O– (R) E1cb reaction
gives Ph-CD=CH2 as the major product.
(D) PhCH2CH2Br and PhCD2CH2Br react with same rate. (S) First order reaction
Cl
2 , Fractional
h
55.  (isomeric products) N   M(isomeric products).
monochlorination distillati on
What are N and M? [JEE 2006]

(A) 6, 6 (B) 6, 4 (C) 4, 4 (D) 3, 3
ORGANIC CHEMISTRY
56. The reagent(s) for the following conversion: [JEE 2007]

Br ?
Br 
 H H
is / are :
(A) alcoholic KOH (B) alcoholic KOH followed by NaNH2
(C) aqueous KOH followed by NaNH2 (D) Zn /CH3OH
57. The major product of the following reaction is [IIT 2008]
H3C Br
F
PhSNa
   
dim ethyl formamide
NO2
H3C Br H3C SPh

H3C SPh H3C SPh
F F SPh SPh
(A) (B) (C) (D)
NO2 NO2 NO2 NO2
58. In the reaction OCH3 HBr

 the products are [IIT 2010]
(A) Br OCH3 and H2 (B) Br and CH3Br
(C) Br and CH3OH (D) OH and CH3Br
59. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using

alcoholic KOH is [IIT 2011]
60. KI in acetone, undergoes SN2 reaction with each of P, Q, R and S. The rates of the reaction vary as
O
Cl
H3C–Cl Cl [JEE Advance 2013]
Cl
P Q R S
(A) P > Q > R > S (B) S > P > R > Q (C) P > R > Q > S (D) R > P > S > Q
ORGANIC CHEMISTRY
61. After completion of the reactions (I and II), the organic compound(s) in the reaction mixtures is(are):
O
Br2(1.0 mol)
Reaction I : H3C CH3 aqueous NaOH [JEE Advance 2013]
(1.0 mol)
O
Br2(1.0 mol)
Reaction I I : H3C CH3 CH3COOH
(1.0 mol)
O O O O O
H2C CH2Br H3C CBr3 Br3C CBr3 BrH2C CH2Br H3C ONa CHBr3
P Q R S T U
(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
62. Match the chemical conversions in List I with the appropriate reagents in List II and select the correct
answer using the code given below the lists: [JEE Advance 2013]
List I List II
(P) Cl (1) (i) Hg(OAc)2; (ii) NaBH4
(Q) ONa OEt (2) NaOEt
OH
(R) (3) Et – Br
(S) (4) (i) BH3 ; (ii) H2O2/NaOH

OH
Codes :
P Q R S
(A) 2 3 1 4
(B) 3 2 1 4
(C) 2 3 4 1
(D) 3 2 4 1
ORGANIC CHEMISTRY
63. The major product in the following reaction is [JEE Advance 2014]
O
Cl 1
. CH 3MgBr , dry ether , 0 C
  
CH3 2. aq. acid
O OH
(A) H3C (B) H C CH3
CH3 2 CH3
CH3
(C) (D)
O CH2 O CH3
64. The major product of the reaction is : [JEE Advance 2015]
H3C CO2H
NaNO2 , aqueous HCl
0°C
CH3 NH2
H 3C NH2 H3C CO2H

(A) (B)
CH3 OH CH3 OH
H3C CO2H H 3C NH2

(C) (D)
CH3 OH CH3 OH
65. In the following monobromination reaction, the number of possible chiral products is
[JEE Advance 2016]
CH2CH2CH3
H Br
CH3 Br (1.0 mole )
2 300
º C
(1.0 mole)
(enantiomerically pure)
66. For the following compounds, the correct statement(s) with respect to nucleophilic substitution reactions
is(are) [JEE Advance 2017]
CH3
CH3
Br Br H3C – C – Br Br
CH3
(I) (II) (III) (IV)
(A) I and III follow SN1 mechanism
(B) Compound IV undergoes inversion of configuration
(C) I and II follow SN2 mechanism
(D) The order of reactivity for I, III and IV is : IV > I > III
ORGANIC CHEMISTRY
67. In the following reaction sequence, the correct structure(s) of X is (are) : [JEE Advance 2018]
Me N3
(1) PBr3,Et2O
X
(2)NaI,Me2CO
(3) NaN3,HCONMe2
enantiomerically pure
Me OH Me OH
(A) (B)
(C) Me (D) Me
OH OH
68. LIST-I contains reactions and LIST-II contains major products. [JEE Advance 2018]
LIST-I LIST-II
P. + 1.
ONa Br OH
Q. + HBr 2.
OMe Br
R. + NaOMe 3.
Br OMe
S. + MeBr 4.
ONa
O
5.
Match each reaction in LIST-I with one or more products in LIST-II and choose the correct option.
(A) P  1,5; Q  2; R  3; S  4 (B) P  1,4; Q  2; R  4; S  3
(C) P  1,4; Q  1,2; R  3,4; S  4 (D) P  4,5; Q  4; R  4; S  3,4
69. Which of the following plots is(are) correct for the given reaction ? [JEE Advance 2020]
([P]0 is the initial concentration of P)
+ NaOH + NaBr
P Q
(A) (B) (C) (D)
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. B 2. B 3. D 4. B 5. A 6. D 7. D
8. B 9. D 10. B 11. D 12. C 13. C 14. C
15. D 16 C 17. B 18. A 19. B 20. A 21. B
22. D 23. A 24. B 25. C 26. B 27. B 28. A
29. A 30. D 31. B 32. C 33. C 34. A 35. A
36. A 37. C 38. D 39. A 40. A 41. D 42. A
43. A 44. D 45. D 46. B 47. B 48. A 49. B
50. D 51. C 52. B 53. D 54. A
[JEE-ADVANCED]
1. 2CHCl3 + O2  2COCl2 + H2O
Phosgene (Poisonous gas)
2. D 3. Fluorine 4. False 5. C
6. False 7. True 9. A 10. A
11. A
conc. H SO Br2 alc.KOH
12.  CH 2  CH 2   H–CC–H
CH3CH2OH  24  CH2= CH2 
 NaNH 2
| |
Br Br
Hg
(CH 3COO )2
  CH 2  CH  OCOCH 3
CH 3COOH vinyl acetate
13. B 14. False 15. True 16. BD
17. AD 18. A 19. C
20. (a) propyl chloride, (b) ortho

21. (i) H2O < CH3OH < HO¯ < CH3O¯
(ii) CH3F < CH3Cl < CH3Br < CH3I
CH3 CH 3
|
Alc.KOH
22. (i) H3C CH2CH3   CH 3  C  CH  CH3
Cl
OH
aq.alkali
|
(ii) CH3CH2CHCl2    [CH 3  CH 2  CH  OH] 
H 2O
 CH3CH2CHO
boil
unstable
23. False
ORGANIC CHEMISTRY
H
Alc.KOH
24. C6H5—CH 2 CH3   C6H5–CH=CH–CH3 HBr
 C 6 H 5  CH  CH 2  CH 3
 |
Br Br
Br
|
25. (i) C 6 H 5  CH  CH  CH 3 ; C 6 H 5  CH  CH 2  CH 3 (ii) C6H5COOMgI + CH4
+
X X
26.
aryl halide
Due to the above resonance phenomena, C–X bond acquire partial double bond character and becomes
difficult to break in the rate determining step of SN2 reaction.
27. SN2 reactions leads to inversion of configuration at -C.
CH3 CH3
NaOH
Br H  H OH
SN 2
C2H5 C2H5
product with inverted
configuration
28. (A) SOCl2 , (B) POCl3 (C) CH3COCl (D) CH 3  C  CH 3

||
O
CH3 CH3
K=1
C – I + I¯ I–C H
29. H
C2H5 C2H5
Above equilibrium is established which has equilibrium constant equal to 1. Therefore, equilibrium mixture
will have both the enantiomers in equal amount giving racemic mixture.
30. + Br2 
31. B
ORGANIC CHEMISTRY
CH 3 CH 3 CH3 CH3
| | | |
32. (X): CH 3  C — CH  CH 3 ; (Y) : CH 2  C — CH  CH3 ; (Z) : CH 3  C  C  CH 3
| | |
Cl CH 3 CH 3
33. (NGP due to MeO, so retention of configuration)
34. E = C6H5COOH ( benzoic acid)

O
|| I2
 C 6 H5  C  CH3  C6H5–COONa + CHI3
NaOH
CH3
CH3
E2
35. CH3 – C – Br + CH3O¯ CH2=C
CH3
CH3
CH3 CH3
S N2
CH3 – C – O¯ + CH3 Br CH3 – C – OCH3
CH3 CH3
36. A 37.
(A) NaNH ( liq .) CH3I

38.  2   (B)
39. D
40. (i) HCl

 
Cl

 ¯

(ii) H Cl

 ¯
ORGANIC CHEMISTRY
CH 3
|
41. D 42. C 43. C 44. CH 3  C  CHCH 3
45. D 46. C 47. B 48. B 49. B
(i ) NaNH
50. CH3CH2 – C  CH   2  CH3CH2 – C  C – CH2CH3
(ii ) CH 3CH 2 Br
X
51. B 52. B 53. A
54. [(A) Q; (B) Q; (C) R,S; (D) P,S] 55. B 56. B 57. A
58. D 59. 5 60. B 61. C 62. A
63. D 64. C 65. 5 66. ACD 67. B
68. B 69. A
ORGANIC CHEMISTRY
ALCOHOL & ETHER

[JEE-MAIN / AIEEE]
Cl2 alc . KOH
1. CH3CH2COOH  A   B. What is B ? [AIEEE-2002 & IIT 1995]
red P
(A) CH3CH2COCl (B) CH3CH2CHO

(C) CH2 = CHCOOH (D) ClCH2CH2COOH
2. On vigorous oxidation by permanganate solution [AIEEE-2002]

(CH3)2C = CH – CH2 – CHO gives
(A) (B)
(C) (D)
3. An ether is more volatile than an alcohol having the same molecular formula. This is due to
(A) dipolar character of ethers [AIEEE-2003]
(B) alcohols having resonance structures
(C) inter-molecular hydrogen bonding in ethers
(D) inter-molecular hydrogen bonding in alcohols
4. Acid catalyzed hydration of alkenes except ethene leads to the formation of [AIEEE-2005]
(A) primary alcohol (B) secondary or tertiary alcohol
(C) mixture of primary and secondary alcohols (D) mixture of secondary and tertiary alcohols
5. Reaction of one molecule of HBr with one molecule of 1, 3-butadiene at 40°C gives predominantly
(A) 3-bromobutene under kinetically controlled conditions [AIEEE-2005]
(B) 1-bromo-2-butene under thermodynamically controlled conditions
(C) 3-bromobutene under thermodynamically controlled conditions
(D) 1-bromo-2-butene under kinetically controlled conditions
6. Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH is
(A) CH3CH2CH(OH)CH2CH3 (B) C6H5CH2CH2OH [AIEEE-2006]
CH3
(C) H3C (D) PhCHOHCH3
OH
ORGANIC CHEMISTRY
Me
7. 
Me

N
– Et
OH n–Bu
The alkene formed as a major product in the above elimination reaction is [AIEEE-2006]
Me Me
(A) Me (B) CH2 = CH2 (C) (D)
8. The compound formed as a result of oxidation of ethyl benzene by KMnO4 is : [AIEEE-2007]

(A) benzophenone (B) acetophenone (C) benzoic acid (D) benzyl alcohol
9. In the following sequence of reactions, the alkene affords the compound 'B'
O3 HO
CH3CH = CHCH3 
 A 2 B. [AIEEE-2008]
Zn
The compound B is
(A) CH3CH2CHO (B) CH3COCH3 (C) CH3CH2COCH3 (D) CH3CHO
10. A liquid was mixed with ethanol and a drop of concentrated H2SO4 was added. A compound with a
fruity smell was formed. The liquid was : [AIEEE-2009]
(A) CH3 CO CH3 (B) CH3 COOH (C) CH3 OH (D) HCHO
11. Iodoform can be prepared from all except : [AIEEE-2012]

(A) Ethyl methyl ketone (B) Isopropyl alcohol
(C) 3-Methyl-2-butanone (D) Isobutyl alcohol
12. Rate of dehydration of alcohols follows the order : [JEE MAINS ONLINE-2013]
(A) 3º > 2º > 1º > CH3OH (B) 2º > 3º > 1º > CH3OH
(C) CH3OH > 1º > 2º > 3º (D) 2º > 1º > CH3OH > 3º
13. An ether (A), C5H12O, when heated with excess of hot concentrated HI produced two alkyl halides
which when treated with NaOH yielded compounds (B) and (C). Oxidation of (B) and (C) gave a
propanone and an ethanoic acid respectively. The IUPAC name of the ether (A) is :
[JEE MAINS ONLINE-2013]
(A) 2-methoxybutane (B) Methoxybutane (C) 2-ethoxypropane (D) Ethoxypropane
LiAlH4 PCl5 Alc. KOH

14. In the reaction, CH3 COOH   A   B   C, the product C is
[JEE MAINS-2014]
(A) Acetylene (B) Ethylene (C) Acetyl chloride (D) Acetaldehyde
ORGANIC CHEMISTRY
15. The most suitable reagent for the conversion of R – CH2 – OH  R – CHO is
(A) K2Cr2O7 (B) CrO3 [JEE MAINS-2014]
(C) PCC (Pyridinium Chlorochromate) (D) KMnO4
16. The gas evolved on heating CH3MgBr in methanol is : [JEE MAINS ONLINE-2016]
(A) Methane (B) Ethane (C) Propene (D) HBr
17. The distillation technique most suited for separating glycerol from spent-lye in the soap industry is :
(A) Simple distillation (B) Fractional distillation [JEE MAINS-2016]
(C) Steam distillation (D) Distillation under reduced pressure
18. The major product formed in the following reaction is : [JEE MAINS (OFFLINE)-2018]
O HI
Heat
O
I OH I OH
(A) (B) (C) (D)
OH OH I I
19. The total number of optically actie compounds formed inthet following reaction is :
[JEE MAINS (ONLINE)-2018]
O
HBr
(A) Two (B) Four (C) Six (D) Zero
20. The main product of the following reaction is : [AIEEE-2010]

conc. H 2SO4
C6H5CH2CH(OH)CH(CH3)2  
H5C6 H C6H5CH2 CH3

(A) C C (B) C C
H CH(CH3) 2 H CH3
C6H5 CH(CH3) 2 H5C6CH2CH2

(C) C C (D) C CH2
H H H3C
21. From amongst the following alcohols the one that would react fastest with conc. HCl and anhydrous
ZnCl2, is [AIEEE-2010]
(A) 2-Butanol (B) 2-Methylpropan-2-ol
(C) 2-Methylpropanol (D) 1-Butanol
ORGANIC CHEMISTRY
22. Consider thiol anion (RS) and alkoxy anion (RO). Which of the following statements is correct ?
(A) RS is less basic but more nucleophilic than RO. [AIEEE-2011]
 
(B) RS is more basic and more nucleophilic than RO .
(C) RS is more basic but less nucleophilic than RO.
(D) RS is less basic and less nucleophilic than RO.
23. An unknown alcohol is treated with the “Lucas reagent” to determine whether the alcohol is primary,
secondary or tertiary. Which alcohol reacts fastest and by what mechanism : [JEE (Mains) 2013]
(A) secondary alcohol by SN1 (B) tertiary alcohol by SN1
(C) secondary alcohol by SN2 (D) tertiary alcohol by SN2
24. 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) K2Cr2O7
25. The product of the reaction given below is : [JEE Main 2019]
(A) (B) (C) (D)
26. The major product of the following reaction is [JEE Main 2019]
O
Hl (excess)

NC O
OH I I OH
(A) (B) (C) (D)
NC OH
NC OH NC I NC I
ORGANIC CHEMISTRY
27. The synonym for water gas when used in the production of methanol is [JEE Main 2019]
(A) natural gas (B) laughing gas (C) syn gas (D) fuel gas
28. The major product of the following reaction is

CH3CH = CHCO2CH3 
LiAIH4
 [JEE Main 2019]
(A) CH3CH = CHCH2OH (B) CH3CH2CH2CH2OH
(C) CH3CH2CH2CO2CH3 (D) CH3CH2CH2CHO
1. PBr3
OH 2. KOH (alc.)
OH
(A) (B) (C) (D)
HO O O O
O
Br
NaBH4
MeOH,25°C
O OH
Br OMe
(A) (B)
OMe O
(C) (D)
ORGANIC CHEMISTRY
OCH3
Conc. HBr (excess)
Heat
CH=CH2
Br OH Br OH
(A) (B) (C) (D)
Br–CHCH3 Br–CHCH3 CH2CH2Br CH2CH2Br
OH
32. CH3CH2 C CH3 cannot be prepared by [JEE Main 2019]
Ph
(A) CH3CH2COCH3 + PhMgX (B) PhCOCH3 + CH3CH2MgX

(C) PhCOCH2CH3 + CH3 + CH3MgX (D) HCHO + PhCH(CH3) CH2MgX
33. What will be the major product when m-cresol is rected with propargyl bromid (HC  C –– CH2Br) in
presence of K2CO3 in acetone ? [JEE Main 2019]
OH
OH
O OH
(A) (B) (C) (D)
H3C
H3C
CH3 CH3
34. Which of the following compounds reacts with ethyl magnesium bromide and also decolourises bromine
water solution [JEE Main 2019]
CN OCH3
CH2––CO2CH3 CH
(A) (B) CH2
OH CN O
(C) (D)
ORGANIC CHEMISTRY
35. An organic compound ‘A’ (C9H10O) when treated with conc. HI undergoes cleavage to yield compound
‘B’ and ‘C’. ‘B’ gives yellow precipitate with AgNO3 where as ‘C’ tautomerizes to ‘D’. ‘D’ gives
positive iodoform test. ‘A’ could be: [JEE Main 2020]
(A) O—CH2—CH—
— CH2 (B) CH2—O—CH —
—CH2
(C) (D) H3C —CH2

O—CH —
36. An organic compound (A) (molecular formula C6H12O2) was hydrolysed with dil. H2SO4 to give a
carboxylic acid (B) and an alcohol (C). ‘C’ gives white turbidity immediately when treated with anhydrous
ZnCl2 and conc. HCl. The organic compound (A) is : [JEE Main 2020]
(A) (B) (C) (D)
37. Which of the following derivatives of alcohols is unstable in an aqueous base ? [JEE Main 2020]
(A) (B) RO – CMe3 (C) (D)
[JEE-ADVANCED]
1. An organic liquid 'A" containing C, H and O with boiling point 78°C, possessing a pleasant odour, on
heating with concentrated sulphuric acid gives a gaseous product 'B' with the empirical formula, CH2. 'B'
decolourises bromine water as well as alkaline permanganate solution and takes up one mole of H2 (per
mole of B) in presence of finely divided nickel at high temperature. Identify the substances A and B.
[JEE 1979]
2. Which of the following is soluble in water? [JEE 1980]

(A) CS2 (B) C2H5OH (C) CCl4 (D) CHCl3
3. Ethyl alcohol is heated with conc. H2SO4. The product formed is [JEE 1980]
(A) CH3COOC2H5 (B) C2H2 (C) C2H4 (D) C2H6
4. The compound which reacts fastest with Lucas reagent at room temperature is [JEE 1981]
(A) butan-2-ol (B) butan-1-ol
(C) 2-methyl propan-1-ol (D) 2-methyl propan-2-ol
5. A compound 'X' containing C, H and O is unreactive towards sodium. It does not add with bromine. It
also does not react with Schiff's reagent. On refluxing with an excess of HI, 'X' yields only one organic
product 'Y'. 'Y' on hydrolysis yields a new compound 'Z' which can be converted into 'Y' by reaction
with red phosphorus and iodine. The compound 'Z' on oxidation with potassium permanganate gives a
carboxylic acid. The equivalent weight of acid is 60. What are the compounds 'X', 'Y' and 'Z'? Write
chemical leading to the conversion of 'X' to 'Y'. [JEE 1981]
ORGANIC CHEMISTRY
6. Diethyl ether on heating with conc. HI give two moles of [JEE 1983]
(A) ethanol (B) iodoform (C) ethyl iodide (D) methyl iodide
7. State the conditions under which the following preparations are carried out. Give necessary equations
which need not be balanced. [JEE 1983]
(i) Ethanol from acetylene
(ii) Tetraethyl lead from sodium-lead alloy
(iii) Methyl chloride from aluminium carbide.
8. An alcohol A, when heated with conc.H2SO4 gives an alkene B. When B is bubbled through bromine
water and the product obtained is dehydro halogenated with excess of sodamide, a new compound C is
obtained. The compound C gives D when treated with warm dilute H2SO4 in presence of HgSO4. D
can also be obtained either by oxidising A with KMnO4 or from acetic acid through its calcium salt.
Identify A, B, C and D. [JEE 1983]
9. Suggest a reason for the large difference between the boiling points of butanol and butanal, although they
have almost the same solubility in water. [JEE 1985]
10. Give a chemical test to distinguish between methanol and ethanol. [JEE 1985]
11. Write down the main product of the following reaction: [JEE 1985]
Ethanol I
2 / NaOH


(C) propan-2-ol (D) 2-methyl propan-1-ol
13. How may be the following transformation be carried out (in not more than six steps)? [JEE 1986]
"Ethyl alcohol to vinyl acetate."
14. Hydrogen bonding is maximum in [JEE 1987]

(A) ethanol (B) diethyl ether (C) ethyl chloride (D) triethyl amine
15. In CH3CH2OH, the bond that undergoes heterolytic cleavage most readily is [JEE 1988]
(A) C–C (B) C–O (C) C–H (D) O–H
16. Arrange the following in increasing order of boiling point: [JEE 1988]
n-butane, n-butanol, n-butylchloride, iso-butane
17. How will you bring about the following conversion? [JEE 1990]
"Ethanal to 2-hydroxy-3-butenoic acid."
18. The products of combustion of an aliphatic thiol (RSH) at 298 K are: [JEE 1992]
(A) CO2(l), H2O (g) and SO2(g) (B) CO2(g), H2O (g) and SO2(g)
(C) CO2(l), H2O (l) and SO2(g) (D) CO2(g), H2O (l) and SO2(l)
19. Compound X (molecular formula, C5H8O) does not react appreciably with Lucas reagent at room
temperature but gives a precipitate with ammoniacal silver nitrate with excess of MeMgBr, 0.42 g of X
gives 224 mL of CH4 at STP. Treatment of X with H2 in presence of Pt catalyst followed by boiling with
excess HI, gives n-pentane. Suggest structure for X and write the equation involved. [JEE 1992]
ORGANIC CHEMISTRY
20. When t-butanol and n-butanol are separately treated with a few drops of dilute KMnO4 in one case
only, purple colour disappears and a brown precipitate is formed. Which of the two alcohols gives the
above reaction and what is the brown precipitate? [JEE 1994]
21. 
The reaction products of C6H5OCH3 + HI  are: [JEE 1995]
(A) C6H5OH + CH3I (B) C6H5I + CH3OH
(C) C6H5CH3 + HOI (D) C6H6 + CH3OI
22. 3,3-Dimethylbutan-2-ol losses a molecule of water in the presence of a concentrated sulphuric acid to
give tetramethyl ethylene as a major product. Suggest a suitable mechanism. [JEE 1996]
23. A compound D (C8H10O) upon treatment with alkaline solution of iodine gives a yellow precipitate. The
filtrate on acidification gives a white solid (E) (C7H6O2). Write the structures of (D) and (E) and explain
the formation of (E). [JEE 1996]
24. The order of reactivity of the following alcohols: [JEE 1997]
towards conc. HCl is:

(A) I > II > III > IV (B) I > III > II > IV (C) IV > III > II > I (D) IV > II > III > I
25. Which of the following is the correct method for synthesising methyl-t-butyl ether and why?
(i) (CH3)3CBr + NaOMe  (ii) CH3Br + tert-BuONa  [JEE 1997]
O  C  OH HOCH 2
Conc.H 2SO 4
26. | + |     (A) [JEE 1997]
O  C  OH HOCH 2
27. Among the following compounds, the strongest acid is: [JEE 1998]
(A) HCCH (B) C6H6 (C) C2H6 (D) CH3OH
28. Discuss why o-hydroxy benzaldehyde is a liquid at room temperature while p-hydroxy benzaldehyde is
a high melting solid? [JEE 1999]
29. Which one of the following will most readily be dehydrated in acidic condition: [JEE 2000]
(A) (B) (C) (D)
30. White the structures of the product A & B [JEE 2000]


CH 3  C  O18C 2 H 5 H3O
A+ B
||
O
ORGANIC CHEMISTRY
31. Cyclobutyl bromide on treatment with magnesium in dry ether forms an organometallic A. The
organometallic reacts with ethanal to give an alcohol B after mild acidification. Prolonged treatment of
alcohol B with an equivalent amount of HBr gives 1-bromo-1-methylcyclopentane (C). Write the structures
of A, B and explain how C is obtained from B. [JEE 2001]
32. Identify X,Y and Z in the following synthetic scheme and write their structure. Explain the formation of
labelled formaldehyde (H2C*O) as one of the products when compound Z is treated with HBr and
subsequently ozonolysed. Mark the C* carbon in the entire scheme. [JEE 2001]
* *
BaC O3 + H2SO4  X (gas) [C denotes C ] 14
(i ) Mg / ether LiAlH4
CH2 = CH – Br    
Y    Z
(ii ) X ,(iii ) H3O
33. Identify the correct order of boiling point of the following compounds: [JEE 2002]
CH3CH2CH2CH2OH CH3CH2CH2CHO CH3CH2CH2COOH
1 2 3
(A) 1 > 2 > 3 (B) 3 > 1 > 2 (C) 1 > 3 > 2 (D) 3 > 2 >1
C H O  Na  (excess)
34. OH + C2H5I 
2 5
    [JEE 2003]
C 2 H5OH (anhydrous)
(A) OC2H5 (B) I (C) C6H5OC6H5 (D) C2H5OC2H5
35. Reaction of entainomerically pure acid with 1 chiral carbon and racemic alcohol with 1 chiral carbon
gives an ester which is: [JEE 2003]
(A) Meso (B) Optically active mixture
(C) Racemic mixture (D) Enantionmerically pure
36. Mention two esters produced when a racemic mixture of 2-phenyl propanoic acid is treated with (+)
2-butanol. What is the stereochemical relationship between these esters? [JEE 2003]
37. On acid catalysed hydration, 2-phenyl propene gives: [JEE 2004]

(A) 3-phenyl-2-propanol (B) 2-phenyl-1-propanol
(C) 1-phenyl-3-propanol (D) 2-phenyl-2-propanol
38. An organic compound P(C5H10O) Reacts 1015 times faster then ethylene with dil.H2SO4 to give two
products Q and R. Both Q and R give positive iodoform test. Identify P, Q and R and also give reason
for very high reactivity of P. [JEE 2004]
39. Phenyl magnesium bromide reacting with t-Butyl alcohol gives [JEE 2005]
(A) Ph – OH (B) Ph – H (C) (D)
ORGANIC CHEMISTRY
40. (X) C5H13N NaNO ,HCl

 2 (Y) (Tertiary alcohol + other products)
N 2
(Optically active)
Find X and Y. Is Y optically active? Write the intermediate steps. [JEE 2005]
41. Statement-1: p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid.[JEE 2007]
because
Statement-2 : o-Hydroxybenzoic acid has intramolecular hydrogen bonding.
42. In the reaction OCH3 HBr

 the products are [JEE 2010]
(A) Br OCH3 and H2 (B) Br and CH3Br
(C) Br and CH3OH (D) OH and CH3Br
43. Amongst the following, the total number of compounds soluble in aqueous NaOH is [JEE 2010]
H3C CH 3
N COOH OCH2CH3 OH
CH2OH
OH
NO2 CH2CH3 COOH
CH 2CH 3
N
H3C CH3
44. The major product of the following reaction is [JEE 2011]
RCH OH
2
  

H (anhydrous )
(A) a hemiacetal (B) an acetal (C) an ether (D) an ester
PREVIOUS YEARS QUESTIONS ORGANIC CHEMISTRY
Alcohol & Ether
45. 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
NaBH4
[Note: C=O CH – OH ] [JEE Advance 2014]
46. The acidic hydrolysis of ether (X) shown below is fastest when [JEE Advance 2014]
OR acid
 OH + ROH
[X]
(A) one phenyl group is replaced by a methyl group.

(B) one phenyl group is replaced by a para-methoxyphenyl group.
(C) two phenyl groups are replaced by two para-methoxyphenyl groups.
(D) no structural change is made to X.
47. 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) [JEE Advance 2018]
O
Ph
OH
Me Ph
X
LIST-I LIST-II
Ph
HO
P. Me + H2SO4 1. I2, NaOH
Ph
OH
Me
Ph
H 2N
Q. H + HNO2 2. [Ag(NH3)2]OH
Ph
OH
Me
ORGANIC CHEMISTRY
Ph
HO
R. Ph + H2SO4 3. Fehling solution
Me
OH
Me
Ph
Br
H + AgNO3
Ph
S. 4. HCHO, NaOH
OH
Me
5. NaOBr
The Correct options 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
48. Choose the correct option(s) for the following set of reactions [JEE Advanced 2019]
(i) MeMgBr conc. HCl

C6H10O O s
(ii) H2O (major)
20% H3PO4, 360 K
(i) H2, Ni HBr, benzolyl peroxide

T R s
(major) (ii) Br2,hv (major) (major)
H3 C Br CH3 CH3 H3C Br

Cl Cl
(A) (B)
U S S T
H3C Cl CH3 CH3 H3C Br

Br Br
(C) (D)
S U U T
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. C 2. B 3. D 4. B 5. B 6. D 7. B
8. C 9. D 10. B 11. D 12. A 13. C 14. B
15. C 16. A 17. D 18. A 19. B 20. A 21. B

22. A 23. B 24. B 25. A 26. D 27. C 28. A
29. C 30. D 31. B 32. D 33. A 34. C 35. B
36. A 37. A
[JEE-ADVANCED]
1. A is ethanol because B is an alkene (Ethane)
C2H5 OH + conc. H2SO4  CH2= CH2 H2 /
Ni
 CH3 – CH3
CH2= CH2 + Br2–H2O(brown) CH2 – CH2  CH2=CH2 + alk.KMnO4 (purple)

Br Br
colourless
CH2 – CH2
OH OH
colourless
2. B 3. C 4. D
5. Compound X must be a symmetrical ether :
HI HI No reaction, not an alcohol Schiffs
R  O  R  2 R  I   ' Re agent
 no reaction, not an
X Y
aldehyde.
H2 O [O]
R–I H
2O
 R– I OH(Z) Acid
EW = 60
I2 /P
R–I
 Acid is CH3 COOH and Z = CH3CH2OH
 X = C2H5–O–C2H5 , Y = CH3–CH2–I
HI
CH3CH2–O–CH2CH3 (X)  2CH3 CH2I (Y)
6. C
HgSO4
7. (i) H–CC–H H2SO4
CH3–CHO Catalyst H2 CH3CH2OH
(ii) 4C2H5 Br + 4(Na/Pb) (sodium-lead alloy) Heat

 (C2H5)4Pb (tetraethyl lead)
(iii) Al4C3 H
2O
 Al(OH)3 + CH4
ORGANIC CHEMISTRY
hv
CH4 + Cl2  CH3Cl + HCl
O

8. (CH3COO)2Ca  CH3–C–CH3 + CaCO3
D
O
H2SO4
CH3–CCH HgSO4 CH3–C–CH3
C D
Br
OH
CH 3–CH=CH2
conc.H2SO4 Br2, H2O
CH3–CH–CH3 CH3–CH=CH2 Br
B (X)
NaNH2
X CH3–CCH
H2O C
9. Butanol forms intermolecular H-bonds, has higher boiling point than butanal.
10. CH3–CH2OH + I2 + NaOH  CHI3  (Iodoform test)

( Yellow )
Iodoform test is not given by methanol.
2 I / NaOH
11. C2H5 OH   CHI3  HCOONa
iodoform
12. A
conc.H SO
13. CH3CH2OH  24  CH2=CH2 Br
2

NaNH 2
CH 2 – CH2   H–CC–H
Br Br
Hg ( CH COO )
3
   2  CH =CH–OCOCH
CH COOH 2 3
3
(Vinyl acetate)
14. A 15. D
16. iso-butane < n-butane < n-butylchloride < n-butanol
OH
17. CH3CHO + HCHO NaOH 

 H – C – CH2–CHO  CH2=CH–CHO
H
Aldol
ORGANIC CHEMISTRY
OH OH

HCN
 CH2 = CH – CH – CN HH
O
CH2 = CH – CH – COOH
2
Cyanohydrin
18. B
19. Above infromation suggest that X has a terminal triple bond and it contain primary – OH group.

H–CC–CH2–CH2–CH2OH Ag

( NH3 ) 2
 Ag–CC–CH2CH2OH
20. n-butanol is oxidised by KMnO4 and not t-butanol as the latter does not contain H atom attached to
carbinol carbon atom.
 
CH3CH2CH2CH2OH + KMnO4  CH 3CH 2CH 2COO O K + MnO2 + KOH
n-Butanol Brown
CH 3
|
CH 3  C  CH 3 + KMnO4  No reaction
|
OH
t-Butanol
21. A
H Me Me
| | H Me
 | |  H 2O  |
22. CH 3  C — C  CH 3 H CH  C — C  CH  CH  C H  C  CH
3 3  3 3
| | |

| | Me
OH Me
 
OH Me 2
Me Me
|  |
H
CH 3  C  C  CH 3   CH 3  CH  C CH 3
| 
|
Me Me
23. (D) Ph  CH  CH 3 (E) C6H5COOH

|
OH
24. C
25. The ether formation involves nucleophilic substitution of alkoxide ion for halide ion.
Slow  Fast
 R ' O ------ R ------ X  R' – O – R + X–
3° alkyl halide can also involve elimination of HX to give alkene in the presence of a base. So, it is better
to start with 3° alkoxide and 1° alkyl halide, i.e., equation (b)
ORGANIC CHEMISTRY
26. 27. D 28. Due to intermolecular H-Bonding
29. A
30. A  CH 3  C  OH , B = C2H5O18H
||
O
H O
31. Mg
 MeCHO
  3
  HBr

Et 2O
(A) (B) (C)

Mechanism
 H O
H 2
  

 Br

2°carbonium 3° carbonium
* * * *
32. X : C O 2 ; Y : C H 2  CH  C OOH ; Z : CH 2  CH C H 2OH ; C H O
2
33. B 34. D 35. B
H
|
Ph H (  ) CH3CH 2 C OH
|
| | CH3
36. CH 3  C  COOH + CH 3  C  COOH     
conc. H 2SO 4 , 
| |
H Ph
(recemic mixture)
Ph H H H
| | | |
CH 3  C  C  O  C  CH 2CH 3  CH 3  C  C  O  C  CH 2 CH 3
| || | | || |
H O CH 3 Ph O CH 3
during esterification reaction only – COOH and – OH participates. There is no effect on structure of
configuration of carbon adjacent of these groups. So when (±) acid reacts with pure (+) alcohol two
esters are produced which are diastereoisomers of each other.
ORGANIC CHEMISTRY
37. D
CH 2
||
38. P : CH 3  CH 2  O  C  CH3
Q : CH3CH2OH
R : CH 3  C  CH 3
||
O
when ethylene reacts with dil. H2SO4CH3CH2 is produced during rate determining step, whereas P
gives resonance stabilized intermediate.
CH 3 CH 3
| |
CH 3  CH 2  O  C  CH 3 CH 3  CH 2  O  C  CH 3
 
due to extra stability of intermediate the rate of reaction is very fast

39. B
OH
|
CCCC
40. X: Y: CCCC
| |
|
C NH 2
C
Y is optically inactive
41. D 42. D 43. 4 44. B 45. 5 46. C 47. D
48. CD
ORGANIC CHEMISTRY
GRIGNARD REAGENT
[JEE-MAIN / AIEEE]
1. Which of these will not react with acetylene ? [AIEEE-2002]
(A) NaOH (B) ammonical AgNO3 (C) Na (D) HCl
2. CH3 – Mg – Br is an organo metallic compound due to [AIEEE-2002]

(A) Mg – Br bond (B) C – Mg bond (C) C – Br bond (D) C – H bond
3. Ethyl isocyanide on hydrolysis in acidic medium generates [AIEEE-2003]

(A) ethylamine salt and methanoic acid (B) propanoic acid and ammonium salt
(C) ethanoic acid and ammonium salt (D) methylamine salt and ethanoic acid
4. Rate of the reaction [AIEEE-2004]
O O
R  Nu  R Z

Z Nu
is fastest when Z is [AIEEE-2004]

(A) Cl (B) OCOCH3 (C) OC2H5 (D) NH2
5. Acetyl bromide reacts with excess of CH3MgI followed by treatment with a saturated solution of NH4Cl
given [AIEEE-2004]
(A) acetone (B) acetyl iodide
(C) 2- methyl -2- propanol (D) acetamide
6. Phenyl magnesium bromide reacts with methanol to give [AIEEE-2006]

(A) a mixture of anisole and Mg(OH)Br (B) a mixture of benzene and Mg(OMe)Br
(C) a mixture of toluene and Mg(OH)Br (D) a mixture of phenol and Mg(Me)Br
7. In the following sequence of reactions, [AIEEE-2007]

P  l2 Mg HCHO H2 O
CH3CH2OH   A 
 B   C  D
ether
the compound ‘D’ is :

(A) butanal (B) n-butyl alcohol (C) n-propyl alcohol (D) propanal
8. Which one of the following is the strongest base in aqueous solution? [AIEEE-2007]
(A) Trimethylamine (B) Aniline (C) Dimethylamine (D) Methylamine
ORGANIC CHEMISTRY
9. The treatment of CH3MgX with CH3C  C–H produces [AIEEE-2008]

(A) CH3 – CH = CH2 (B) CH3C  C – CH3
H H
(C) CH3—C C—CH3 (D) CH4
10. A major component of Borsch reagent is obtained by reacting hydrazine hydrate with which of the
following ? [IIT Mains Online 2013]
Cl Cl
Cl Cl
O2N NO2 NO2
O2N NO2 NO2
(A) (B) (C) (D)
NO2 NO2
11. The hydrocarbon with seven carbon atoms containing a neopentyl and a vinyl group is :
[IIT-JEE Mains (online) 2016]
(A) 2, 2-dimethyl-4-pentane (B) 4, 4-dimethylpentene
(C) Isopropyl-2-butene (D) 2, 2-dimethyl-3-pentene
12. The “N” which does not contribute to the basicity for the compound is :
[IIT-JEE Mains (online) 2016]
(A) N7 (B) N1 (C) N9 (D) N3
13. The gas evolved on heating CH3MgBr in methanol is [JEE Mains (online) 2016]
(A) Methane (B) Ethane (C) Propene (D) HBr
ORGANIC CHEMISTRY
14. The major product B formed in the following reaction sequence is [JEE Main (online ) 2018]
CHO
(i) C2H5MgBr
A HCl B
(ii) H2O
MeO
Cl
(A) (B) Cl
MeO Cl
(C) (D)
MeO MeO
[JEE-ADVANCED]
1. Write the structural formula of main organic product formed when ethyl acetate is treated with double the
molar quantity of methyl magnesium bromide and the reaction mxiture is poured into water.
[JEE 1981]
2. Identify the major product. [JEE 1993]
C6H5COOH + CH3MgI  ? + ?
3. Predict the major product. [JEE 1994]

(i ) CH MgBr (excess )
C6H5– CH2COCH3  3    
(ii ) H
4. Which of the following is an organometallic compound? [JEE 1997]

(A) Lithium methoxide (B) Lithium acetate
(C) Lithiumdimethylamide (D) Methyl lithium
5. (CH3)3CMgCl on treatment with D2O produces [JEE 1997]

(A) (CH3)3CD (B) (CH3)3COD (C) (CD)3CD (D) (CD)3COD
6. C4 H8O2 CH MgBr

3 P, the product 'P' will be [JEE 2003]
(excess)
Ethyl ester
(A) (B) (C) (D)
7. Order of rate of reaction of following compounds with phenyl magnesium bromide is: [JEE 2004]
Ph  C  Ph Me  C  H Me  C  Me
|| || ||
O O O
(I) (II) (III)
(A) I > II > III (B) II > III > I (C) III > I > II (D) II > I > III
ORGANIC CHEMISTRY
CH 3
|
8. Ph – MgBr + CH3  C  OH  A [JEE 2005]
|
CH 3
CH 3 CH 3
| |
(A) (B) CH 3
 C  OPh (C) (D) CH 3  C  Ph
| |
CH 3 CH 3
9. Identify the reaction mechanism : [JEE 2011]
10. The major product in the following reaction is [JEE Advance 2014]
O
Cl 1. CH 3MgBr , dry ether , 0 C
  
CH3 2. aq. acid
O OH
(A) H3C (B) H C CH3
CH3 2 CH3
CH3
(C) (D)
O CH2 O CH3
Paragraph for question nos. 11 & 12
In the following reactions : [JEE Advance 2015]
C8 H 6 Pd
BaSO 4
 C8 H 8 i
. B2H6
 X
H2 ii . H 2O 2 , NaOH , H 2O
 H 2O
 HgSO 4 , H 2SO 4
C8 H8O i
. EtMgBr , H 2O
      Y
ii . H  , Heat
11. Compound X is
O OH
(A) CH3 (B) CH3
OH
CHO
(C) (D)
ORGANIC CHEMISTRY
12. The major compound Y is
(A) CH 3 (B) CH 3
CH2 CH3
CH3
(C) (D) CH3
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. A 2. B 3. A 4. A 5. C 6. B 7. C
8. C 9. D 10. D 11. B 12. C 13. A 14. A
[JEE-ADVANCED]
O
||
H O
1. CH 3  C  OC2 H 5  2CH 3MgBr  
2
 ]
OH
|
C6 H 5  CH 2 — C — CH 3
2. C6H5COO¯ Mg I + CH4 3. |
CH 3
4. D 5. A 6. A 7. B 8. A
O O CH2–Cl O
|| CH3MgI Cl  Ph
9. Ph  C  CH 2  CH 2  CH 2  Cl   Ph – C – CH2CH2 
H3 C
CH3
10. D 11. C 12. D
ORGANIC CHEMISTRY
OXIDATION-REDUCTION OF ORGANIC COMPOUND
[JEE-MAIN]
1. An organic compound [A], molecular formula C10H20O2 was hydrolysed with dilute sulphuric acid to
given a carboxylic acid [B] and an alcohol [C]. Oxidation of [C] with CrO3 – H2SO4 produced [B].
Which of the following structures are not possible for [A] [JEE-Main Online 2020]
(A) (B)
(C) (CH3)3–C– COOCH2C(CH3)3 (D) CH3CH2CH2COOCH2CH2CH2CH3
2. Consider the following reaction : [JEE-Main Online 2020]
The product 'P' gives positive ceric ammonium nitrate test. This is because of the presence of which of
these –OH group(s) ?
(A) (b) only (B) (d) only (C) (b) and (d) (D) (c) and (d)
[JEE-ADVANCED]
OBJECTIVE
1. Which of the following will decolourise alkaline KMnO4 solution? [JEE 1980]
(A) C3H8 (B) CH4 (C) CCl4 (D) C2H4
2. The reagent with which both acetaldehyde and acetone react easily is [JEE 1981]
(A) Tollen's reagent (B) Schiff's reagent (C) Grignard reagent (D) Fehling reagent
3. When acetaldehyde is treated with Fehling's solution, it gives a precipitate of [JEE 1982]
(A) Cu (B) CuO (C) Cu2O (D) Cu + Cu2O + CuO
4. Baeyer's reagent is [JEE 1984]

(A) alkaline permanganate solution (B) acidified permanganate solution
(C) neutral permanganate solution (D) aqueous bromine solution
5. Hydrogenation of benzoyl chloride in the presence of Pd on BaSO4 gives [JEE 1992]

(A) benzyl alcohol (B) benzaldehyde (C) benzoic acid (D) phenol
ORGANIC CHEMISTRY
6. The appropriate reagent for the following transformation: [JEE 2000]
O
CH2CH3
CH3
HO HO
(A) Zn(Hg), HCl (B) NH2NH2, OH¯ (C) H2 / Ni (D) NaBH4
7. Statement-1: Dimethyl sulphide is commonly used for the reduction of an ozonide of an alkene to get
the carbonyl compound. [JEE 2001]
Statement-2: It reduces the ozonide giving water soluble dimethyl sulpoxide and excess of it evaporates.
8. 1-propanol and 2-propanol can be best distinguished by [JEE 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 H2SO4 followed by reaction with Fehling solution.
9. Butan-2-one can be converted to propanoic acid by which of the following? [JEE 2006]
(A) NaOH, NaI / H+ (B) Fehling solution
(C) NaOH, I2 / H + (D) Tollen's reagent
COMPREHENSION :
In the following sequence, product I, J and L are formed. K represents a reagent. [JEE 2008]
(i ) Mg / Ether
Cl
(i ) NaBH4
Hex-3-ynal   I   K
 J  (ii ) CO2
H3C  H
2

 L
 Pb / BaSO 4 quinoline
(ii ) PBr3 (iii ) H 3O
O
10. The structure of the product I is
(A) H C Br (B) H3C

3
Br
H3C
Br
(C) H C Br (D)
3
ORGANIC CHEMISTRY
11. The structures of compound J and K, respectively, are
H3C COOH and SOCl2
(A) (B) H C and SO2Cl2
3 COOH
H3C
(C) & SOCl2 (D) H3C COOH and CH3SO2Cl
COOH
12. The structure of product L is

H3C
CHO
(A) (B) H C CHO
3
H3C
(C) (D) H C CHO
3
CHO
13. The most suitable reagent for the conversion of R–CH2 – OH  R – CHO is :[JEE Main 2014]
(A) K2Cr2O7 (B) CrO3
(C) PCC (Pyridinium Chlorochromate) (D) KMnO4
14. Reagent(s) which can be used to bring about the following transformation is(are) [JEE Advance 2016]
O O O O
C O C
H OH
COOH COOH
(A) LiAlH4 in (C2H5)2O (B) BH3 in THF

(C) NaBH4 in C2H5OH (D) Raney Ni/H2 in THF
SUBJECTIVE
1. One mole of a hydrocarbon A reacts with 1 mol of bromine giving a dibromo compound, C5H10Br2.
Compound A on treatment with cold dilute alkaline potassium permanganate solution forms a compound,
C5H12O2. On ozonolysis, A gives equimolar quantities of propanone and ethanal. Deduce the structural
formula of A. [JEE 1981]
2. A white precipitate was formed slowly when silver nitrate was added to compound A with the molecular
formula C6H13Cl. Compound A on treatment with hot alcoholic potassium hydroxide gave a mixture of
two isomeric alkenes B and C, having the formula C6H12. The mixture of b and C, on ozonolysis,
furnished four compounds. [JEE 1986]
(a) CH3CHO (b) C2H5CHO (c) CH3COCH3 (d) CH 3  CH  CHO

|
CH 3
What are the structures of A, B and C?
ORGANIC CHEMISTRY
3. Write the balanced chemical equations for the following: [JEE 1991]
"Ethylene glycol is obtained by the reaction of ethylene with potassium permanganate".
4. When gas A is passed through dry KOH at low temperature, a deep-red coloured compound B and a
gas C are obtained. Gas A, on reaction with but-2-ene, followed by treatment with Zn/H2O yields
acetaldehyde. Identify A, B and C. [JEE 1994]
5. An organic compound E(C5H8) on hydrogenation gives compound F(C5H12). Compound E on ozonolysis

gives formaldehyde and 2-ketopropanal. Deduce the structure of compound E. [JEE 1995]
6. Hydrocarbon A adds 1 mol of hydrogen in the presence of a platnium catalyst to form n-hexane. When
A is oxidised vigorously with KMnO4, a single carboxylic acid, containing three carbon atoms, is isolated.
Give the structure of A and explain. [JEE 1997]
7. Monomer A of a polymer on ozonolysis yields 2 mol of HCHO and 1 mol of CH3COCHO.

(a) Deduce the structure of A. [JEE 2005]
(b) Write the structure of all cis forms of polymer of compound A.
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN]
1. B 2. A
[JEE-ADVANCED]
OBJECTIVE
1. D 2. C 3. C 4. A 5. B 6. B 7. A
8. C 9. C 10. D 11. A 12. C 13. C 14. CD
SUBJECTIVE
CH3 Br2 CH3

C = CH – CH3 C – CH – CH3
1. CH3 (i ) CH3
(ii O3 Br Br
)H
cold & 2O
/Z
dil. KMnO4 n
CH3
CH3 C = O + OHC – CH3
C = CH – CH3 CH3
CH3 Propanone Ethanol
OH OH
CH3 – CH – CH – CH2 – CH3

CH3 Cl (A)
Alc. KOH
2.
CH3 – C = CH – CH2 – CH3 + CH3 – CH – CH = CH – CH3
CH (B) (C)
3 CH 3
O3
O3
CH3
C = O + OHC – C2H5 CH3 – CH – CHO + OHC – CH3
CH3
CH3
CH2 +
CH2 – OH
cold dil. KMnO4/H
3.
CH2 CH2 – OH
O3
4. KOH  
Gas ( A ) KO3(B) + O2(C)
Pottasium ozonide (Deep Red Coloured)
O3 ( A )
CH3 – CH = CH – CH3   
(ii ) Zn / H 2O 2CH3 – CHO
(A)  O3 ; (B)  KO3 ; (C)  O3
ORGANIC CHEMISTRY
CH2 O
5. CH3 – C – CH = CH2 CH3 – C – CHO + CH 2O
(E) 2-Keto propanol Formaldehyde
H2
CH3
CH3 – CH – CH2 – CH 3
6. CH3 – CH2 – CH = CH – CH2– CH2 CH3 – CH2 – CH2 – CH2 – CH2– CH2
(A)
KMnO4 / 
2CH3 – CH2 – COOH
CH3 O
CH2 Ozonolysis O O
7. (a) +
CH2 H H CH3 H
CH3 H CH3 H
CH2 CH 2
C C C
C
(b) CH2 CH2
CH3
ORGANIC CHEMISTRY
CARBONYL COMPOUND
[JEE-MAIN / AIEEE]
1. Trichloroacetaldehyde was subjected to Cannizzaro's reaction by using NaOH. The mixture of the products
contains sodium trichloroacetate ion and another compound. The other compound is :
(A) 2, 2, 2–Trichloroethanol (B) Trichloromethanol [AIEEE 2011]
(C) 2, 2, 2–Trichloropropanol (D) Chloroform
2. Ozonolysis of an organic compound 'A' produces acetone and propionaldehyde in equimolar mixture.
Identify 'A' from the following compounds : [AIEEE 2011]
(A) 1-Pentene (B) 2-Pentene
(C) 2-Methyl-2-pentene (D) 2-Methyl-1-pentene
3. Iodoform can be prepared from all except : [AIEEE 2012]

(A) Ethyl methyl ketone (B) Isopropyl alcohol
(C) 3–Methyl–2–butanone (D) Isobutyl alcohol
4. In the given transformation, which of the following is the most appropriate reagent ?
[AIEEE 2012]
Re agent
 


(A) NH2NH2, O H (B) Zn–Hg/HCl (C) Na, Liq, NH3 (D) NaBH4
5. The correct sequence of reagents for the following conversion will be : [JEE Mains - 2017]
(A) [Ag(NH3)2] OH , H /CH3OH, CH3MgBr (B) CH3MgBr, H /CH3OH, [Ag(NH3)2]+OH–
+ – + +
(C) CH3MgBr, [Ag(NH3)2]+OH–, H+/CH3OH (D) [Ag(NH3)2]+OH–, CH3MgBr, H+/CH3OH
6. The major product of the following reaction is [JEE-MAIN 2019]
HO (i) CrO 3
(ii) SoCl 2/
(iii) 
HO
O O
O O
(A) (B) (C) (D)
HO Cl
HO Cl
ORGANIC CHEMISTRY
7. The major product Y in the following reaction is [JEE-MAIN 2019]
Ph CH3
NaOCl (i) SOCl2
X (ii) Aniline Y
O
O NH2
Ph
N NH2 Ph
HN Ph
O
O
(A) (B) (C) (D)
Ph
O
Ph
8. The major product of the following reaction is [JEE-MAIN 2019]
O
O HO CH3
NaBH4
EtOH
HO CH3
CHO
CHO
OH
OH O OH
(A) (B) (C) (D)
OEt
9. The increasing order of the following compounds towards HCN addition is : [JEE-MAIN 2020]
(i) (ii)
(iii) (iv)
(A) (iii) < (i) < (iv) < (ii) (B) (i) < (iii) < (iv) < (ii)
(C) (iii) < (iv) < (ii) < (i) (D) (iii) < (iv) < (i) < (ii)
ORGANIC CHEMISTRY
10. The increasing order of the reactivity of the following compounds in nucleophile addition reaction is:
Propanal, Benzaldehyde, Propanone, Butanone [JEE-MAIN 2020]
(A) Benzaldehyde > Butanone < Propanone < Propanal
(B) Butanone < Propanone < Benzaldehyde < Propanal
(C) Benzaldehyde < Propanal < Propanone < Butanone
(D) Propanal < Propanone < Butanone < Benzaldehyde
11. The compound A in the following reactions : [JEE-MAIN 2020]
(A) (B)
(C) (D)
12. The number of chiral centres present in [B] is .............. [JEE-MAIN 2020]
13. Consider the following reactions : [JEE-MAIN 2020]
(I2 + NaOH)
'B' yellow ppt

Ag2O
silver mirror

ORGANIC CHEMISTRY
(I2 + NaOH)

no yellow ppt
'C'
LiA1H4 Anhydrous ZnCl2
'D' gives white turbidity
& Conc. HCl
within 5 minutes
‘A’ is
(A) (B) (C) (D)
14. The correct match between Item – I (starting material) and Item-II (reagent) for the preparation of
benzaldehyde is: [JEE-MAIN 2020]
Item-I
(I) Benzene (P) HCl and SnCl2, H3O+
(II) Benzonitrile (Q) H2, Pd-BaSO4,S and quinoline
(III) Benzoyl Chloride (R) Co, HCl and AlCl3
(A) (I)-(R), (II)-(Q) and (III)-(P) (B) (I)-(Q), (II)-(R) and (III)-(P)
(C) (I)-(P), (II)-(Q) and (III)-(R) (D) (I)-(R), (II)-(P) and (III)-(Q)
[JEE-ADVANCED]
1. Which reagent both acetaldehyde and acetone react easily is [JEE 1981]
(A) Tollen's reagent (B) Schiff's reagent (C) Grignard reagent (D) Fehling reagent
2. Write the structural formula of the main organic product formed when methanal reacts with ammonia.
[JEE 1981]
3. Outline the reaction sequence for the conversion of methanal to ethanal (the number of steps should not
be more than three) [JEE 1981]
4. A compound that gives a positive iodoform test is [JEE 1982]

(A) 1-pentanol (B) 3-pentanone (C) 2-pentanone (D) pentanal
5. An alkene 'A' on ozonolysis yields acetone and an aldehyde. The aldehyde is easily oxidised to an acid
'B'. When 'B' is treated with bromine in presence of phosphorus yields a compound 'C' which on hydrolysis
gives a hydroxyl acid 'D'. This acid can also be obtained from acetone by the reaction with hydrogen
cyanide followed by hydrolysis. Identify the compounds A,B,C and D. [JEE 1982]
6. When acetaldehyde is treated with Fehling's solution, it gives a precipitate of [JEE 1983]
(A) Cu (B) CuO (C) Cu2O (D) Cu + Cu2O + CuO
7. The Cannizzaro's reaction is not given by [JEE 1983]

(A) trimethyl acetaldehyde (B) acetaldehyde
(C) benzaldehyde (D) formaldehyde
ORGANIC CHEMISTRY
8. Base catalysed aldol condensation occurs with [JEE 1984]
(A) propionaldehyde (B) benzaldehyde
(C) 2-methyl propionaldehyde (D) 2,2-dimethyl propionaldehyde
9. Which of the following compounds will give a yellow precipitate with iodine and alkali?
(A) 2-hydroxy propane (B) Acetophenone [JEE 1984]
(C) Methyl acetate (D) Acetamide
10. Which of the following compounds will react with ethanolic KCN? [JEE 1984]
(A) Ethyl chloride (B) Acetyl chloride
(C) Chlorobenzene (D) Benzaldehyde
11. Show with balanced equation, what happens, when the following are mixed: [JEE 1984]
"Chloral is heated with aqueous hydroxide"
12. Which of the following will not react with alkali and iodine is [JEE 1985]
(A) acetone (B) ethanol (C) diethyl ketone (D) isopropyl alcohol
13. Arrange the following in order of their increasing reactivity towards HCN : [JEE 1985]
CH3CHO, CH3COCH3, HCHO, C2H5COCH3
14. Write down product of the following reaction. [JEE 1985]

NaOH
Propanal 
heat
15. Give reason in one or two sentences for the following [JEE 1986]
"Hydrazones of aldehydes and ketones are not prepared in highly acidic medium"
16. How may the following transformation be carried out (in not more than six steps) "Benzaldehyde to
cyanobenzene"? [JEE 1986]
17. Complete the following with appropriate structures [JEE 1986]
? NaOH
 CH=CH–CHO
18. Which of the following compounds is oxidised to prepare methyl ethyl ketone? [JEE 1987]
(A) 2-propanol (B) 1-butanol (C) 2-butanol (D) t-butyl alcohol
19. Answer the followings with suitable equations wherever necessary [JEE 1987]
(i) Suggest a reagent to distinguish acetaldehyde from acetone.
(ii) What happens when excess chlorine is passed through boiling toluene in the presence of sunlight?
ORGANIC CHEMISTRY
20. Which of the following is/are an example of aldol condensation? [JEE 1989]
(A) 2CH3CHO dil
. NaOH
 CH3CH(OH)CH2CHO
OH
|
(B) 2CH3COCH3 dil
. NaOH
 H 3C — C — CH 2COCH 3
|
CH 3
(C) 2HCHO dil

. NaOH
 CH3OH + HCOONa
(D) C6H5CHO + HCHO dil
. NaOH
 C6H5CH2OH + HCOONa
21. A ketone A, which undergoes haloform reaction, gives compound B on reduction. B on heating with
sulphuric acid gives compound C, which forms mono-ozonide D. D on hydrolysis in presence of zinc
dust gives only acetaldehyde. Identify A,B and C. Write down the reactions involved. [JEE 1989]
22. The formation of cyanohydrin from a ketone is an example of: [IIT 1990]
(A) Electrophilic addition
(C) Nucleophilic substitution (D) Electrophilic substitution
23. 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
24. 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
25. Give reason in one or two sentences: [JEE 1991]

"Iodoform is obtained by the reaction of acetone with hypoiodite but not with iodide."
26. Hydrogenation of benzoyl chloride in the presence of Pd and BaSO4 gives: [IIT 1992]
(A) Benzyl alcohol (B) Benzaldehyde (C) Benzoic acid (D) Phenol
27. Arrange the following in increasing order of expected enol content. [JEE 1992]
CH3COCH2CHO, CH3COCH3, CH3CHO, CH3COCH2COCH3
28. Write the structure of the major organic product expected from the following reaction. [JEE 1992]
MeO CHO + HCHO KOH


29. An organic compound C3H6O does not give a precipitate with 2,4-Dinitrophenyl hydrazine reagent and
does not react with metallic sodium. It could be: [IIT 1993]
(A) CH3CH2CHO (B) CH3COCH3
(C) CH2=CH–CH2OH (D)CH2=CH–O–CH3
ORGANIC CHEMISTRY
30. Under Wolff Kishner reduction conditions, the conversions which may be brought about is?
(A) Benzaldehyde into Benzyl alcohol (B) Cyclohexanol into Cyclohexane
(C) Cyclohexanone into Cyclohexanol (D) Benzophenone into Diphenylmethane
[IIT 1995]
31. In the reaction, P is [IIT 1995]

SeO
CO 2  P + Se + H2O
(A) CH3COCHO (B) CH3COOCH3 (C) CH3COCH2OH (D) None
NaOC H in absolute
32. C6H5–CHO + CH3 – COOC2H5  25   (D). [IIT 1995]
C2 H 5OH and heat
 
33. In the Cannizzaro reaction given below, 2Ph–CHO OH  Ph–CH2OH + PhCO 2 the slowest step is:
(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–CH2OH [IIT 1996]
34. C = O (
i ) KCN / H 2SO 4
   D. [IIT 1996]
(ii ) LiAlH 4
35. Suggest appropriate structures for the missing compounds. (the number of carbon atoms remains the
same throughout the reaction) [JEE 1996]
CH3
dil
.KMnO
4  A HIO
4  B HO
¯  C

CH3
36. Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is
(A) MeCOCl (B) MeCHO (C) MeCOOMe (D) MeCOOCOMe
[IIT 1997]
37. In a Cannizzaro reaction the intermediate which is the best hydride donor is: [IIT 1997]
H H
| |

(A) C 6 H 5  C  O (B) C 6 H 5  C  O 
| |
OH O
(C) (D)
38. CH3CHO + H2NOH  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
ORGANIC CHEMISTRY
39. Complete the following, giving the structures of the principal organic products [JEE 1997]
O
(i) + Ph3P = CH2  A
(ii) ClCH2CH2CH2COPh + KOH MeOH

 B
O
C6H5 
(iii) H3C + NaOH H3O C
O
40. Acetophenone on reaction with hydroxylamine-hydrochloride can produce two isomeric oximes. Write
structures of the oximes. [IIT 1997]
41. Among the following compounds, which will react acetone to give a product containing > C = N–
(A) C6H5NH2 (B) (CH3)3N (C) C6H5NHC6H5 (D) C6H5NHNH2
[IIT 1998]
42. The product obtained via oxymercuration (HgSO4–H2SO4) of 1-butyne would be

O
||
(A) CH 3CH 2  C  CH 3 (B) CH3CH2CH2CHO
(C) CH3CH2CHO + HCHO (D) CH3CH2COOH + HCOOH [IIT 1998]
43. Which of the following will undergo aldol condensation: [IIT 1998]
(A) Acetaldehyde (B) Propanaldehyde
(C) Benzaldehyde (D) Trideutero acetaldehyde
44. Which of the following will react with water: [IIT 1998]
(A) CHCl3 (B) Cl3CCHO (C) CCl4 (D) ClCH2CH2Cl
45. 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
46. Write the intermediate steps for each of the following reactions. [JEE 1998]

(i) C6H5CH (OH)C CH H
3O
 C6H5CH = CHCHO

(ii) H
OH O CH3
47. An aldehyde (A) (C11H8O), 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]
(i ) LiAlH
48. (
C)
   4  (D) [IIT 1998]
(ii ) H  ,heat
ORGANIC CHEMISTRY
49. 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
50. The appropriate reagent for the following transformation: [IIT 2000]

(A)Zn(Hg), HCl (B) NH2NH2, OH– (C) H2/Ni (D) NaBH4
51. What would be the major product in each of the following reaction? [IIT 2000]
Base

52. Identify (A), (B) and (C), and give their structures. [IIT 2000]
Br
2 A + B

NaOH
C (C7H12O)
53. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
(A) benzyl alcohol and sodium formate (B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate (D) benzyl alcohol and methyl alcohol [IIT 2001]
54. 1-propanol & 2-propanol can be best distinguished by: [JEE 2001]
(A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution
(B) Oxidation with acedic dichromate followed by reaction with Fehling solution
(C) Oxidation by heating with copper followed by reaction with Fehling solution
(D) Oxidation with concentrated H2SO4 followed by reaction with Fehling solution
55. An alkene (A) C16H16 on ozonolysis gives only one product (B) C8H8O. Compound (B) on reaction
with NaOH / I2 yields sodium benzoate. Compound (B) reacts with KOH / NH2 NH2 yielding a
hydrocarbon (C) C8H10. Write the structures of compound (B) and (C). Based on this information two
isomeric structures can be proposed for alkene (A). Write their structures and identify the isomer which
on catalytic hydrogenation (H2 / Pd–C) gives a racemic mixture. [JEE 2001]
56. A compound C9H7O2Cl exists predominantly in enol form (A) and also in keto form (B). On oxidation
with KMnO4 it gives m-chlorobenzoic acid as one of the products. Identify the compounds (A) and (B).
[JEE 2001]
57. Compound A (molecular formula C3H8O) is treated with acidified potassium dichromate to form a
product B (molecular formula C3H6O). B forms a shining silver mirror on warming with ammonical silver
nitrate. B when treated with an aqueous solution of H2NCONHNH2. HCl and sodium acetate gives a
product C. Identify the structure of C.
ORGANIC CHEMISTRY
CH 3
|
(A) CH3CH2CH = NNHCONH2 (B) CH 3  C  NNHCONH 2
|
CH 3
(C) CH 3  C  NCONHNH2 (D) CH3CH2CH=NCONHNH2 [IIT 2002]

|
CH3
58. Five isomeric para-disubstituted aromatic compounds A to E with molecular formula C8H8O2 were
given for identification. Based on the following observations, give structure of the compounds.
(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. [IIT 2002]
59. Write structures of the products A, B, C, D and E in the following scheme. [IIT 2002]
Na  Hg HNO / H SO
CH2CH2CH3 Cl / FeCl 3
2    A  
3
 B   2 
4  C
HCl
CH CHCH O  Na  H / Pd / C
 D 2  E
2  2  
CHO OHC
(i ) NaOH(excess)100 C
60.       [IIT 2003]
(ii ) H  / H 2 O
CHO OHC
any one of the products formed is :
COOH HOOC CH2OH CH2OH
(A) (B)
COOH HOOC CH2OH CH2 OH
O
CH2OH COOH O
(C) (D)
COOH CH2OH O
O
61. Acidic
 Products formed by P & Q can be differentiated by: [IIT 2003]
Hydrolysis
(A) 2, 4 DNP (B) Lucas reagent (ZnCl2) conc. HCl

(C) NaHSO3 (D) Fehlings solution
ORGANIC CHEMISTRY
62. C6H12 HCl

 C6H13Cl + (C)
(A) (B)
ozonolysis
(D)   (E)
NaOH
(A) ozonolysis
  (F) + (G)  HCOONa + 1° alcohol
(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]
63. 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
CH COONa
64. + X 3  [IIT 2005]
What is X?
(A) CH3COOH (B) BrCH2, COOH (C) (CH3CO)2O (D) CHO–COOH
65. The smallest ketone and its next homologue are reacted with NH2OH to form oxime.Which statement is
correct about this :
(A) Two different oximes are formed (B) Three different oximes are formed
(C) Two oximes are optically active (D) All oximes are optically active [JEE 2006]
66. 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 [JEE 2007]
(A) (B) (C) (D)
67. 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.
(D) Statement-1 is False, Statement-2 is True. [JEE 2007]
ORGANIC CHEMISTRY
Paragraph for Question Nos. 68 to 70 (3 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 salicylaldeydes as depicted below.
 [I]   aq

. HCl

(Intermediate)
68. Which one of the following reagents is used in the above reaction? [JEE 2007]
(A) aq. NaOH + CH3Cl (B) aq. NaOH + CH2Cl2
(C) aq. NaOH + CHCl3 (D) aq.NaOH + CCl4
69. The electrophile in this reaction is [JEE 2007]
(A)  CHCl (B) +CHCl2 (C)  CCl 2 (D)  CCl 3
70. The structure of the intermediate I is [JEE 2007]
(A) (B)
(C) (D)
71. 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 OMR. [JEE 2007]
Column I Column II
(A) C6H5CHO (P) gives precipitate with
2,4-dinitrophenylhydrazine
(B) CH3CCH (Q) gives precipitate with AgNO3
(C) CN– (R) is a nucleophile
(D) I– (S) is involved in cyanohydrin formation
Paragraph for Question No. 72 to 74
In the following reaction sequence, products I, J and L are formed. K represents a reagent.
1. Mg / ether
1. NaBH 4 2. CO Cl H
2
Hex-3-ynal    I  2  J 
K Me L
3. H O Pd/BaSO4
2. PBr3 3 || quinoline
O
72. The structure of the product I is [JEE 2008]
Me
(A) Me Br (B)
Br
Me Br
(C) Me Br (D)
ORGANIC CHEMISTRY
73. The structures of compounds J and K, respectively are [JEE 2008]
OH
(A) Me COOH and SOCl2 (B) Me || and SO2Cl2
O
(C) Me and SOCl2 (D) Me COOH and CH3SO2Cl
COOH
74. The structure of product L is [JEE 2008]

Me CHO
(A) (B) Me CHO
CHO
(C) (D) Me CHO
Me

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.
O
H3C
Ph
M=
Ph H
75. Compound H is formed by the reaction of

O O
|| ||
(A) + PhMgBr (B) + PhCH2MgBr
Ph CH3 Ph CH3
O O Me
(C) || + PhCH2MgBr (D) || +
Ph H Ph H Ph MgBr
76. The structure of compound I is [JEE 2008]
Ph CH3 H 3C Ph CH3 H3C CH3

Ph
(A) (B) (C) (D)
H Ph H Ph H CH2Ph Ph H
77. The structures of compounds J, K and L, respectively, are [JEE 2008]

(A) PhCOCH3, PhCH2COCH3 and PhCH2 COO¯K+
(B) PhCHO, PhCH2CHO and PhCOO¯K+
(C) PhCOCH3, PhCH2CHO and CH3COO¯K+
(D) PhCHO, PhCOCH3 and PhCOO¯K+
ORGANIC CHEMISTRY
Paragraph for Question Nos. 78 to 80
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. O
1. MeMgBr
P  Q  3  R 1
. OH ¯
 S
2. Zn , H O
2. H , H 2O 2.  2
3. H 2SO 4 , 
78. The structure of the carbonyl compound P is [JEE 2009]

Me
(A) (B)
O Me O Me
O
(C) (D)
O Et
Me
79. The structure of the products Q and R, respectively, are [JEE 2009]
O
Me H
(A) , COMe
Me
Me Me Me
H
(B) , CHO
Me
Me Me Me
H
(C) , CHO
Et
Me Me Et
Me O
CH3
(D) , CHO
Me Me Et
80. The structure of the product S is [JEE 2009]

O O
O
Me
(A) (B) (C) (D)
O
Me Me Me Me
Me
ORGANIC CHEMISTRY
Paragraph for Questions 81 to 83

Two aliphatic aldehydes P and Q react in the presence of aqueous K2CO3 to give compound R, which
upon treatment with HCN provides compound S. On acidification and heating, S gives the product
shown below:
H3C OH
H3C
O
O
81. The compounds P and Q respectively are [JEE 2010]
CH3
CH H H
and H3C
(A) H3C C C
O O
CH3
CH H H H
and
(B) H3C C C
O O
H
H3C CH 2 H and H3C
CH C C
(C)
CH3 O O
H3C CH 2 H H H
and
CH C C
(D)
CH3 O O
82. The compound R is [JEE 2010]

O
O
H3C C
H 3C C
C H
(A) C H (B)
H 3C H3C
CH
CH2
H3C OH
OH
CH3 O CH3 O
CH C CH C
H3C CH H H3C H
CH
(C) (D)
CH2 CH
OH H3 C OH
ORGANIC CHEMISTRY
83. The compound S is [JEE 2010]
CH3 O O
CH C H3C C
H3C CH H CH H
(A) (B) H3C
CH2 CH2
CN CN
CH3 CN CN
CH CH H3C CH
H3C OH C OH
CH
(C) (D) H3C
CH2
CH2
OH OH
84. In the scheme given below, the total number of intramolecular aldol condensation products formed from
‘Y’ is [IIT 2010]
1. O
 3  Y 1
. NaOH ( aq )
 
2. Zn , H O
2
85. Match the reactions in column I with appropriate types of steps / reactive intermediate involved in these
reactions as given in column II [JEE 2011]
Column I Column II
(A) (P) Nucleophilic substitution
(B) (Q) Electrophilic substitution
(C) (R) Dehydration
(D) (S) Nucleophilic addition
(T) Carbanion
ORGANIC CHEMISTRY
Paragraph for Questions 86 & 87
An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product
through the following sequence of reactions, in which Q is an intermediate organic compound.
86. The structure of compound P is [IIT 2011]

(A) CH3CH2CH2CH2 – CC–H (B) H3CH2C – C  C– CH2CH3
(C) (D)
87. The structure of the compound Q is [IIT 2011]
(A) (B)
OH
|
(C) (D) CH 3CH 2CH 2CHCH 2CH 3
Paragraph for Questions 88 to 89

In the following reaction sequence, the compound J is an intermediate.
(CH 3CO) 2 O (i) H 2 , Pd / C
I CH COONa J K
3 (ii ) SOCl2
(iii ) anhyd. AlCl3
J (C9H8O2) gives effervescence on treatment with NaHCO3 and a positive Baeyer's test.
88. The compound 'K' is : [JEE 2012]
(A) (B) (C) (D)
ORGANIC CHEMISTRY
89. The compound 'I' is : [JEE 2012]
(A) (B) (C) (D)
90. With reference to the scheme given, which of the given statement(s) about T, U, V and W is (are)
correct? [JEE 2012]
O
O
H3C T
LiAlH4
 excess
CrO3/H (CH3CO)2O
V U W
(A) T is soluble in hot aqueous NaOH
(B) U is optically active
(C) Molecular formula of W is C10H18O4
(D) V gives effervescence on treatment with aqueous NaHCO3
91. Among P, Q, R and S, the aromatic compound(s) is / are [JEE Advance 2013]
Cl
AlCl
3  P
NaH
 Q
(
NH 4 )2 CO3
 R
100115C
O O
O
HCl
 S
(A) P (B) Q (C) R (D) S
ORGANIC CHEMISTRY
Paragraph For Questions 92 to 93
Schemes 1 and 2 describe sequential transformation of alkynes M and N. Consider only the major
products formed in each step for both the schemes.
Scheme–1
Scheme–2
92. The product X is [JEE Advance 2014]

H
H3CO
(A) (B) H3CO H
H H
H
CH3CH2O
(C) (D) CH 3CH2O H
H H
93. The correct statement with respect to product Y is [JEE Advance 2014]
(A) It gives a positive Tollens test and is functional isomer of X
(B) It gives a positive Tollens test and is a geometrical isomer of X
(C) It gives a positive iodoform test and is a functional isomer of X.
(D) it gives a positive iodoform test and is a geometrical isomer of X.
94. The major product of the following reaction is [JEE Advance 2015]
O
i
. KOH , H 2O



ii . H , heat
CH3
O
CH3 CH3
O O
(A) (B)
O
O CH3
(C) CH3 (D)
ORGANIC CHEMISTRY
95. In the following reactions, the product S is [JEE Advance 2015]

H3C
i. O3 NH3
R S
ii. Zn, H2O
H 3C H3C N
N
(A) (B)
N N
(C) (D)
H 3C H 3C
96. Positive Tollen's test is observed for [JEE Advance 2016]

H O
CHO OH
Ph O
(A) H H (B) (C) Ph (D)
O Ph Ph
H
97. The major product of the following reaction sequence is [JEE Advance 2016]
O
i
) HCHO (excess)/N aOH, heat
    
ii ) HCHO/H (catalytic amount)
O O OH
(A) (B)
O OH
HO
(C) (D)
OH
98. Compounds P and R upon ozonlysis produce Q and S, respectively. The molecular formula of Q and S
is C8H8O. Q undergoes Cannizzaro reaction but not haloform reaction, whereas S undergoes haloform
reaction but not Cannizzaro reaction. [JEE ADVANCE 2017]
i) O3/CH2Cl2
(i) P ii) Zn/H2O
Q
(C8H8O)
i) O3/CH2Cl2
(ii) R ii) Zn/H2O
S
(C8H8O)
The option(s) with suitable combination of P and R, respectively, is(are)
ORGANIC CHEMISTRY
(A) H3C and

CH3
H3C CH3
CH3 CH3
(B) and
CH3
CH3
H3C
CH3 CH3
(C) and
CH3
H3C
(D) H3C and H3C

CH3
99. The reaction(s) leading to the formation of 1,3,5-trimethylbenzene is(are) [JEE ADVANCE 2018]
O
Conc. H 2SO4 heated iron tube
(A) (B) Me H
 873 K
O
(1) Br2, NaOH CHO
+
(2) H3O
(C) (D) Zn/Hg, HCl
(3) sodalime, 
OHC CHO
O O
Paragraph for Question Nos. 100 and 101 [IIT-JEE Advance 2018]
Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3/CuCl followed by reaction with
Ac2O/NaOAc gives compound X as the major product. Compound X upon reaction with Br2/Na2CO3,
followed by heating at 473 K with moist KOH furnishes Y as the major product. Reaction of X with H2/
Pd-C, followed by H3PO4 treatment gives Z as the major product.
(There are two questions based on Paragraph "X", the question given below is one of them)
100. The compound Y is
OH
COBr Br
(A) (B)
HO O
Br
COBr
(C) (D)
Br
PREVIOUS YEARS QUESTIONS ORGANIC
CarbonylCHEMISTRY
Compound
101. The compound Z is
OH
(A) (B) (C) (D)

O O O
Paragraph for Question Nos. 102 and 103 [IIT-JEE Advance 2018]
An organic acid P (C1H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol
to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P
undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another
set of reactions to produce S.
(1) H2/Pd-C
(2) NH3/ (1) H2/Pd-C (1) HCl
(3) Br2/NaOH (2) SOCl2 (2) Mg/Et2O
S P Q R
(4) CHCl3, KOH,  (3) MeMgBr, CdCl2 (3) CO2(dry ice)
+
(5) H2/Pd-C (4) NaBH4 (4) H3O
(There are two questions based on PARAGRAPH "A", the question given below is one of them)
102. The compound R is
HO2C
CO2H
(A) (B)
CO2H
CO2H
(C) (D)
103. The compound S is
H
N
(A) (B) (C) NH2 (D)
HN
NH2
ORGANIC CHEMISTRY
104. In the following reaction sequence, the amount of D(in g) formed from 10 moles of acetophenone
is_______.
(Atomic weights in g mol–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) [JEE ADVANCE : 2018]
O
NaOBr NH3, Br2/KOH Br2(3 equiv)

+ A B C D
H3O AcOH
(60%) (50%) (50%) (100%)
Answer the following by appropriately matching the lists based on the information given in the paragraph
(Q.105 to Q.106) [IIT Adv. 2019]
List-I includes starting materials and reagents of selected chemical reactions. List -II gives structures of
compound that may be formed as intermediate products and/or final products form the reactions of
List-I.
List-I List-II
i) DIBAL-H
CN ii) dil. HCl CHO
(I) (P)
O iii) NaBH4
iv) conc.H2SO4 CO2H
O
i) O3
ii) Zn, H2O OH
(II) iii) NaBH4 (Q)
OH
CO2H iv) conc.H2SO4
i) KCN
+
ii) H3O , 
Cl
(III) iii) LiAlH4 (R) O
CO2CH3 iv) conc.H2SO4
CO2Me OH
i) LiAlH4
(IV) ii) conc.H2SO4 (S)
CO2Me
CO2H
CO2H
(T)
CO2H
(U) O
105. Which of the following options has correct combination considering List-I and List-II ?
(A) (I), (Q), (T), (U) (B) (II), (P), (S), (U) (C) (II), (P), (S), (T) (D) (I), (S), (Q), (R)
ORGANIC CHEMISTRY
106. Which of the following options has correct combination considering List-I and List-II ?
(A) (III), (S), (R) (B) (IV), (Q), (U)
(C) (III), (T), (U) (D) (IV), (Q), (R)
107. Total number of hydroxyl groups present in a molecule of the major product P is ________.
[IIT Adv. 2019]
(i) H2, Pd-BaSO4, quinoline

P
(ii) dil. KMnO4(excess), 273 K
108. Total number of isomers, considering both structural and stereoisomers, of cyclic ethers with the molecular
formula C4H8O is _______. [IIT Adv. 2019]
109. Choose the correct option(s) for the following reaction sequence : [IIT Adv. 2019]
2+
(i) Hg , dil. H2SO4 (i) SOCl2
CHO (ii) AgNO3, NH4OH pyridine Zn-Hg,
Q R S
(iii) Zn-Hg, conc. HCl (ii) AlCl3 Conc. HCl
MeO
Consider Q, R and S as major products
CO2H
(A)
MeO MeO
O
(Q) (R)
OH
CO2H
(B)
MeO MeO
(Q) (S)
(C)
MeO MeO
O
(R) (S)
(D)
MeO MeO
O
(R) (S)
ORGANIC CHEMISTRY
110. Consider the following transformations of a compound P. [IIT Adv. 2020]
Choose the correct options(s).
(A) P is (B) X is Pd-C/quinoline/H2
(C) P is (D) R is
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. A 2. C 3. D 4. A 5. A 6. B 7. B
8. A 9. A 10. B 11. B 12. D 13. A 14. D
[JEE-ADVANCED]
1. C 2. (CH2)6N4
O
|| CH MgBr PCC
3. H  C  H 3 CH3–CH2–OH  CH3–CHO 4. C
H 3O
O OH OH
|| |  |
H
5. CH 3  C  CH3 HCN 
 CH 3  C  CN H 2O CH 3  C  COOH
| |
CH 3 CH 3
( D)
Br CH 3 CH 3 CH 3
| | | |
C = CH 3  C  COOH , B = CH 3  CH  COOH , A = CH 3  C  CH  CH  CH 3
|
CH 3
6. C 7. B 8. A 9. AB 10. ABD
aq OH ¯
11. CCl3–CHO    HCOO  + CHCl3 12. C
13. III > I > II > IV 14.
CH 3  CH  CH  CH 2  CH3
|
CHO
15. Hydrazine form salt therefore no further reaction with aldehyde & ketones.
C – H + CH3–CHO
16. 17. 18. C
O
19. (i) Tollen's reagent (ii) Benzo chloride is obtained 20. AB
O
||
21. (A) CH 3  C  CH 2  CH 3 (B) CH 3  CH  CH 2  CH3
|
(C) CH3 – CH = CH – CH3 OH
22. B 23. A 24. D
25. Hypoiodite is oxidising reagent whereas I¯ is reducing agent.
26. B 27. I > IV > II > III 28. MeO CHO + HCHO
29. D 30. D 31. A
ORGANIC CHEMISTRY
32. C6H5CH = CHCOOC2H5
(D)
33. B 34. C
(a racemic mixture)
CH3
OH CH3 O
O
35. (A) (B) (C)
O
CH3
HO CH3 CH3
36. A 37. D 38. B
CH2
O
39. (i) (ii) Ph–C
40. C 6 H 5  C  CH 3 and C 6 H 5  C  CH 3
|| ||
N  OH HO  N
syn anti (isomers )
41. AD 42. A 43. ABD 44. B 45. BD

 +
46. (i) C6H 5 – CH – C C–H H C6H 5 – CH – C C–H
 H 2O
OH OH
O
 ||
H
 C 6 H5  CH  CH  C  H  C 6 H5  CH  C  C  OH
|
H

H

(ii) + H

OH O O CH3
H
CH=CH–CC–CHO
CHO CHO 
47. Ozonolysis
  
 + 2| Ag
 COOH
COOH |
COOH
(A)
(B) (Oxalic acid)
6 5 C H CHO
48.  
 Base
(C) (D) 49. B 50. B
ORGANIC CHEMISTRY
51. Base

52. Br NaOH + CHBr3

2  

(A) (B) (C)
53. A 54. C
O
Ph Ph Ph CH3 C–CH3 CH2–CH3
55. (A) C=C + C=C (B) (C)
CH3 CH3 CH3 Ph
H
O O O
CHO COOH
H
56. KMnO
 4 
Cl Cl Cl
(A) (B)
57. A
O
CHO CHO CH2 CHO COOH O–CH=CH2
C–CH3
58. (A) or (B) (C) (D) (E)
OCH3 CH2 OH OH CH3 OH

OH
O NO2 NO2
C–Pr Bu Bu Bu
59. (A) (B) Cl (C) (D) Cl

Cl Cl
Cl Cl O–CH2–CH=CH2
Cl
NH2
Bu
(E) 60. C 61. D
Cl
O–Pr
ORGANIC CHEMISTRY
62. Me3C – CH=CH2 HCl

 Me2 C –CHMe2 + Me3C– CH –Me
| |
Cl Cl
(A) (B) (C)
alc.KOH Me
(i) O3
Me2C = CMe2 + C=O
(ii) Zn/H3O
(D) Me
(E)
(A) Ozonolysis
  HCHO + Me3C–CHO NaOH
(F) (G)
HCOONa + Me3C–CH2OH (1°alcohol)
63. C 64. C 65. B 66. A 67. C 68. C 69. C

70. B 71. (A) P, S; (B) Q; (C) Q, R, S; (D) Q,R 72. D 73. A 74. C
75. B 76. A 77. D 78. B 79. A 80. B 81. B
82. A 83. D 84. 1 85. (A) R,S,T (B) P,S,T (C) R,S (D) Q,R
86. D 87. B 88. C 89. A 90. ACD 91. ABCD
92. A 93. C 94. A 95. A 96. ABC 97. A 98. AC
99. ABD 100. C 101. A 102. A 103. B 104. 495 105. B
106. D 107. 6.00 108. 10.00 109. AC 110. BC
ORGANIC CHEMISTRY
CARBOXYLIC ACID AND ITS DERIVATIVE

[JEE-MAIN / AIEEE]
1. Sodium ethoxide has reacted with ethanoyl chloride. The compound that is produced in the above
reaction is : [AIEEE-2011]
(A) Diethyl ether (B) 2-Butanone (C) Ethyl chloride (D) Ethyl ethanoate
2. A compound with molecular mass 180 is acylated with CH3COCl to get a compound with molecular
mass 390. The number of amino groups present per molecule of the former compound is :
[JEE(Mains) 2013]
(A) 2 (B) 5 (C) 4 (D) 6
3. Compound (A), C8H9Br, gives a white precipitate when warmed with alcoholic AgNO3. Oxidation of
(A) gives an acid (B), C8H6O4. (B) easily forms anhydride on heating. Identify the compound (A).
[JEE (Mains) 2013]
CH2Br
CH2Br C2H5 CH2Br
(A) (B) (C) (D)
Br CH3
CH3 CH3
4. 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 CH3CH2NH2. A is [JEE (Mains) 2013]
(A) CH3COOH (B) CH3CH2CH2COOH
(C) (D) CH3CH2COOH
5. In the Hofmann bromamide degradation reaction, the number of moles of NaOH and Br2 used per mole
of amine produced are : [JEE (Mains) 2016]
(A) Four moles of NaOH and two moles of Br2
(B) Two moles of NaOH and two moles of Br2
(C) Four moles of NaOH and one mole of Br2
(D) One mole of NaOH and one mole of Br2
ORGANIC CHEMISTRY
6. Which of the following compounds will form significant amount of meta products during mono-nitration
reaction? [JEE (Mains) 2017]
OH OCOCH3 NH2 NHCOCH3
(A) (B) (C) (D)
7. Sodium salt of an organic acid ‘X’ produces effervescene with conc. H2SO4. ‘X’ reacts with the acidi-
fied aqueous CaCl2 solution to give a white precipitate which decolourises acidic solution of KMnO4.
‘X’ is : [JEE (Mains) 2017]
(A) C6H5COONa (B) HCCONa (C) CH3COONa (D) Na2C2O4
8. The major product obtained in the following reaction is [JEE (Mains) 2017]
O
O
DIBAL – H
COOH
OH OH
CHO CHO
(A) (B)
COOH CHO
CHO CHO
(C) (D)
COOH CHO
9. Which of the following compounds will be suitable for Kjeldahl's method for nitrogen estimation ?
[JEE (Mains) 2018]
(A) (B) (C) (D)
10. The increasing order of basicity of the following compounds is : [JEE (Mains) 2018]
NH2 NH
(a) (b)
NH2
(c) (d) NHCH3
NH
(A) (b) < (a) < (c) < (d) (B) (b) < (a) < (d) < (c)
(C) (d) < (b) < (a) < (c) (D) (a) < (b) < (c) < (d)
ORGANIC CHEMISTRY
11. Which dicarboxylic acid in presence of a dehydrating agent is least reactive to give an anhydride ?
[2019 Mains]
CO2H CH2
CH2 COOH
(A) (B)
CO2H CH2 COOH
CH2
COOH C
CH2 OH
(C) (D)
COOH CH2 OH
C
12. The major product of the following reaction is [2019 Mains]
OH
CH2OH
H2SO4 (cat.)
CHCl3
CO2Et
O O OH OH
(A) (B) (C) (D)

OEt
O
CO2Et COOH
O O
13. The major product of the following reaction is [2019 Mains]
O Cl
(i) AlCl3, heat

O +
(ii) H2O
ORGANIC CHEMISTRY
O CO2H
Cl
(A) (B)
Cl O
O
O Cl O
(C) (D)
COOH Cl
O
14. The increasing order of the reactivity of the following with LiAlH4 is [2019 Mains]
O O O O O
(A) (B) (C) (D)

C2H5 NH2 C2H5 OCH3 C2H5 Cl C2H5 O C2H5
(A) (A) < (B) < (D) < (C) (B) (A) < (B) < (C) < (D)
(C) (B) < (A) < (D) < (C) (D) (B) < (A) < (C) < (D)
15. The major product obtained in the following reaction is [2019 Mains]
CO2Et
O
O
O O
(A) (B)
CO2Et
CO2Et
O O
(C) (D)
CO2Et
CO2Et
ORGANIC CHEMISTRY
16. The decreasing order of case of alkaline hydrolysis for the following esters is [2019 Mains]
COOC2H5 Cl COOC2H5
(I) (II)
O2N COOC2H5 CH3O COOC2H5
(III) (IV)
(A) III > II > IV > I (B) III > II > I > IV (C) II > III > I > IV (D) IV > II > III > I
17. The compound A and B in the following reaction are, respectively [2019 Mains]
HCHO  HCl AgCN


 A  B
(A) A = Benzyl alcohol, B = Benzyl isocyanide

(B) A = Benzyl alcohol, B = Benzyl cyanide
(C) A = Benzyl chloride, B = Benzyl isocyanide
(D) A = Benzyl chloride, B = Benzyl cyanide
18. The major product of following reaction is [2019 Mains]

(i) AIH(i.Bu )
R  C  N 
(ii) H O
2

2
(A) RCHO (B) RCONH2 (C) RCOOH (D) RCH2NH2
19. The major product of the following reaction is [JEE-Main 2019]

OH
Ethyle formate (1 equiv.)
CH3 CH CH2CH2NH2 
Triethylamine

OH
(A) CH3 CH CH2CH2NHCHO (B) CH3 = CH––CH2NH2
O
OH
(C) CH3 –– CH –– CH = CH2 (D) O H
CH3CHCH 2CH2NH2
ORGANIC CHEMISTRY
20. Ethylamine (C2H5NH2) can be obtained from N-ethylphthalimide on treatment with
[JEE-Main 2019]
(A) NaBH4 (B) NH2NH2 (C) H2O (D) CaH2
21. Hinsberg’s reagent is [JEE-Main 2019]

(A) SOCl2 (B) C6H5COCl (C) C6H5SO2Cl (D) (COCl)2
22. Which of the following amines can be prepared by Gabriel phthalimide reaction ?
[JEE-Main 2019]
(A) n-butylamine (B) triethylamine (C) t-butylamine (D) neo-pentylamine
23. A compound ‘X’ on treatment with Br2/NaOH, provided C3H9N, which gives positive carbylamine test.
Compound ‘X’ is [JEE-Main 2019]
(A) CH3COCH2NHCH3 (B) CH3CH2CH2CONH2
(C) CH3CON(CH3)2 (D) CH3CH2COCH2NH2
24. The major product of the following reaction is [JEE-Main 2019]
CH3N NaBH4
OH O
(A) CH3N (B) CH3NH
OH OH
(C) CH3NH (D) CH3N
25. The major product formed in the reaction given below will be [JEE-Main 2019]
NH2
NaNO2
Aq.HCl,0-5°C
(A) NO 2 (B) OH
NO2 OH
(C) (D)
ORGANIC CHEMISTRY
26. The major product obtained in the following reaction is [JEE-Main 2019]
OH
(CH3CO)2 O/pyridine (1eqv.)

room temperature
NH2
COCH3
OH OH
(A) (B)
NH2 NHCOCH3
OCOCH3
(C) (D)
NHCOCH3 NH2
27. The major products of the following reaction are [JEE-MAIN 2019]
OH
(1) CHCl3/aq.NaOH
(2) HCHO, NaOH (conc.)
(3) H3 O+
Cl
OH OH
COOH COOH
(A) and methanol (B) and methanol
Cl OH
OH OH
OH OH
(C) and formic acid (D) and formic acid
OH Cl
ORGANIC CHEMISTRY
28. Major products of the following reaction are [JEE-MAIN 2019]
CHO
(i) 50% NaOH

+HCHO (ii) H3O
+
COOH
(A) CH3OH and HCO2H (B) CH3OH and
CH2OH
CH2OH COOH
(C) HCOOH and (D) and
[JEE-ADVANCED]
1. Statement-1 : Acetate ion is more basic than the methoxide ion.
Statement-2 : The acetate ion is resonance stabilized. [JEE-2004]
(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
2. In conversion of 2-butanone to propanoic acid which reagent is used. [JEE-2005]
(A) NaOH, NaI / (B) Fehling solution (C) NaOH, I2 / (D) Tollen's reagent
Passage (3 and 4) [JEE 2006]
X II


3. Which reagent (X) is used to convert I to II

(A) KBr / NaOH (B) Br2 / NaOH (C) NaHCO3 (D) N-Bromo succinimide
ORGANIC CHEMISTRY
4. Which step is rate determining step [JEE 2006]
(A) Formation of II (B) Formation of III (C) Formation of V (D) Formation of IV
5. + under Hofmann conditions will give : [JEE 2006]
(A) + (B) +
(C) + (D) +
6. Statement-1 : p-Hydroxybenzoic acid has a lower boiling point that o-hydroxybenzoic acid.
Statement-2 : o-Hydroxybenzoic acid has intramolecular hydrogen bonding. [JEE 2007]
Statement-1
7. In the reaction T, the structure of the
Product T is : [JEE-2010]
(A) (B)
(C) (D)
8. The major product of the following reaction is : [JEE-2011]
ORGANIC CHEMISTRY
(A) (B)
(C) (D)
9. The carboxyl functional group (– COOH) is present in : [JEE-2012]

(A) picric acid (B) barbituric acid (C) ascorbic acid (D) aspirin
10. The compound that undergoes decarboxlylation most readily under mild condition is :[JEE-2012]
(A) (B)
(C) (D)
11. With reference to the scheme given, which of the given statements(s) about T, U, V and W is (are)
correct? [JEE-2012]
(A) T is soluble in hot aqueous NaOH

(B) U is optically active
(C) Molecular formula of W is C10H18O4
(D) V gives effervescence on treatment with aqueous NaHCO3
ORGANIC CHEMISTRY
12. The total number of carboxylic acid groups in the product P is [JEE(Advanced)-2013]
Paragraph for Question 13 and 14 [JEE(Advanced)-2013]

P and Q are isomers of dicarboxylic acid C4H4O4. Both decolorize Br2/H2O. 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.
13. Compounds formed form 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
14. In the following reaction sequences V and W are respectively : [JEE(Advanced)-2013]

H / Ni
Q 2 V
+ V 
AlCl3 ( anhydrous)
     W
1 . Zn Hg / HCl
2. H3PO 4
O
CH2OH
(A) O and (B) and
CH2OH
O W O W
V V
O
HOH2C
(C) O and (D) and
CH2OH CH2OH
V W
W
V O
ORGANIC CHEMISTRY
15. The major product of the following reaction is [JEE(Advanced)-2017]
OH
i) NaNO2, HCl, 0°C

ii) aq. NaOH
NH2
ONa+ OH
(A) (B)
N2Cl Cl
OH
N=N OH
(C) (D)
N=N
PARAGRAPH (16-17) [JEE(Advanced)-2018]

An organic acid P (C11H12O2) can easily be oxidized to a dibasic acid which reacts with ethyleneglycol
to produce a polymer decron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P
undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another
set of reactions to produce S.
1) H 2 / Pd  C 1) HCl
2) NH3 /  1) H 2 / Pd  C
2) Mg/Et 2 O 2)SOCl2
S   Q 
 P 
3) Br2 / NaOH
3) CO 2 (dry ice)
4) CHCl3 .KOH, 
R
3) MeMgBr,CdCl2
 4) NaBH 4 4) H3 O
5) H 2 / Pd  C
16. The compound R is

HO2C
CO2H
(A) (B)
CO2H
CO2H
(C) (D)
ORGANIC CHEMISTRY
17. The compound S is
(A) (B)
NH2 HN
H
N
(C) NH2 (D)
18. Aniline reacts with mixed acid (conc. HNO3 and conc. H2SO4) at 288 K to give P (51%), Q (47%) and
R (51%), Q(47%) and R (2%). The major product(s) of the following reaction sequence is/are
[JEE(Advanced)-2018]
(1)Ac 2 O,pyridine (1)Sn /HCl

(2)Br2 ,CH 3CO 2 H (2)Br2 / H 2 O
R 
(3)H O 
 S 
(3)NaNO 2 ,HCl/273  278K
 major product(s)
3
(4) NaNO 2 ,HCl/ 273  278K (4)H 3 PO 2
(5)EtOH, 
Br Br
Br Br
(A) (B)
Br Br
Br Br
Br Br
(C) (D)
Br Br Br Br
Br
ORGANIC CHEMISTRY
19. 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
NH2
(i) Br2(excess), H2O
(ii) NaNO2, HCl, 273 K
(iii) CuCN/KCN
Scheme 1 : Q
(iv) H3O+, D
(major)
(v) SoCl2, pyridine
P
(i) Oleum
Scheme 2 : +
S
(iii) H
(major)
(iv) Br2, CS 2, 273 K
R
(i) NaHO
Scheme 3 : (ii) Q
T
(major)
20. In the following reaction, compound Q is obtained from compound P via an ionic intermediate.
What is the degree of unsaturation of Q ?
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. D 2. B 3. D 4. D 5. C 6. C 7. D
8. B 9. A 10. B 11. B 12. D 13. D 14. A
15. B 16. B 17. C 18. A 19. A 20. B 21. C
22. A 23. B 24. C 25. B 26. B 27. D 28. C
[JEE-ADVANCED]
1. D 2. C 3. B 4. D 5. A 6. D 7. C
8. A 9. D 10. B 11. A,C,D 12. 2 13. B 14. A
15. C 16. A 17. B 18. D 19. 4.00 20. 18
ORGANIC CHEMISTRY
NAME REACTIONS
[JEE-ADVANCED]
(OBJECTIVE)
1. m-chlorobenzaldehyde on reaction with conc. KOH at room temperature gives: [JEE 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
 
2. In the Cannizzaro reaction given below, 2Ph–CHO OH
 Ph–CH2OH + PhCO 2 the slowest step is:
(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–CH2OH [JEE 1996]
3. In a Cannizzaro reaction the intermediate which is the best hydride donor is: [JEE 1997]
H H
| |

(A) C 6 H 5  C  O (B) C 6 H 5  C  O 
| |
OH O
(C) (D)
4. Which of the following will undergo aldol condensation: [JEE 1998]

(A) Acetaldehyde (B) Propanaldehyde
(C) Benzaldehyde (D) Trideutero acetaldehyde
5. A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives:
(A) benzyl alcohol and sodium formate [JEE 2001]
(B) sodium benzoate and methyl alcohol
(C) sodium benzoate and sodium formate
(D) benzyl alcohol and methyl alcohol
ORGANIC CHEMISTRY
CHO OHC
(i ) NaOH(excess)100 C
6.       [JEE 2003]
(ii ) H  / H 2 O
CHO OHC
any one of the products formed is :
COOH HOOC CH2OH CH2OH
(A) (B)
COOH HOOC CH2OH CH2 OH
O
CH2OH COOH O
(C) (D)
COOH CH2OH O
O
CH COONa
7. + X 3  [JEE 2005]
What is X?
(A) CH3COOH (B) BrCH2, COOH
(C) (CH3CO)2O (D) CHO–COOH
8. 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
[JEE 2007]
(A) (B)
(C) (D)

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.
O
H3C
Ph
M=
Ph H
ORGANIC CHEMISTRY
9. Compound H is formed by the reaction of [JEE 2008]
O O
|| ||
(A) + PhMgBr (B) + PhCH2MgBr
Ph CH3 Ph CH3
O O Me
(C) || + PhCH2MgBr (D) || +
Ph H Ph H Ph MgBr
10. The structure of compound I is [JEE 2008]
Ph CH3 H 3C Ph
(A) (B)
H Ph H Ph
Ph CH3 H3C CH3

(C) (D)
H CH2Ph Ph H
11. The structures of compounds J, K and L, respectively, are [JEE 2008]

(A) PhCOCH3, PhCH2COCH3 and PhCH2COO¯K+
(B) PhCHO, PhCH2CHO and PhCOO¯K+
(C) PhCOCH3, PhCH2CHO and CH3COO¯K+
(D) PhCHO, PhCOCH3 and PhCOO¯K+
12. The number of aldol reaction (s) that occurs in the given transformation is [JEE 2012]
OH
OH
conc. aq. NaOH
CH3CHO + 4HCHO    

HO
OH
(A) 1 (B) 2 (C) 3 (D) 4
SUBJECTIVE
1. Write the chemical equation to show what happens when [JEE 1981]
" Ethyl acetate is treated with sodium ethoxide in ethanol and the reaction mixture is acidified".
NaOC H in absolute
2. C6H5–CHO + CH3 – COOC2H5  25   (D). [JEE 1995]
C2 H 5OH and heat
3. (
C)
 [JEE 1998]
ORGANIC CHEMISTRY
4. In the scheme given below, the total number of intramolecular aldol condensation products formed from
‘Y’ is [JEE 2010]
1. O
 3  Y 1
. NaOH ( aq )
 
2. Zn , H O
2 2. heat
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-ADVANCED]
OBJECTIVE
1. D 2. B 3. D 4. ABD 5. A 6. C 7. C
8. A 9. B 10. A 11. D 12. C
SUBJECTIVE
O O
||
 CH3 C OC2 H 2
1. CH3COOC2H5 C
2 H 5O
 C H 2COOC2 H5     CH3–C–CH2–COO2H5
Claisen Condensation
O
+
H
H2O
C2H5OH + CH3–C–CH2COOH
2. C6H5CH = CHCOOC2H5
(D)
3. (C) C 6 H 5CHO / Base 4. 1
ORGANIC CHEMISTRY
PHENOL & ANILINE

(CARBENE & NITRENE MECHANISM BASED)
[JEE-MAIN / AIEEE]
OCOCH3
COOH
1. The compound is used as [AIEEE-2002]
(A) antiseptic (B) antibiotic (C) analgesic (D) pesticidie
2. When primary amine reacts with chloroform in ethanoic KOH then the product is
[AIEEE-2002]
(A) an isocynide (B) an aldehyde (C) a cyanide (D) an alcohol
3. The reaction of chloroform with alcoholic KOH and p-toluidine form [AIEEE-2003]
(A) H3C CN (B) H3C N2Cl
(C) H3C NHCHCl2 (D) H3C NC
– +
OH O Na
4. + CHCl3 + NaOH
CHO
The electrophile involved in the above reaction is [AIEEE-2006]

(A) dichloromethyl cation (CHCl2) (B) dichlorocarbene(: CCl2)
– 
(C) trichloromethyl anion (CCl3) (D) formyl cation (CHO)
5. In the chemical reaction, [AIEEE-2007]

CH3CH2NH2 + CHCl3 + 3KOH  (A) + (B) + 3H2O, the compound (A) and (B) are respectively
(A) C2H5CN and 3KCl (B) CH3CH2CONH2 and 3KCl
(C) C2H5NC and K2CO3 (D) C2H5NC and 3KCl
6. The major product obtained on interaction of phenol with sodium hydroxide and carbon dioxide is :
[AIEEE-2009]
(A) salicylic acid (B) pthalic acid (C) benzoic acid (D) salicylaldehyde
7. Aspirin is known as : [AIEEE-2012]

(A) Acetyl salicylic acid (B) Phenyl salicylate (C) Acetyl salicylate (D) Methyl salicylic acid
8. 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 CH3CH2NH2. A is : [IIT-JEE Mains 2013]
(A) CH3CH2COOH (B) CH3COOH
(C) CH3CH2CH2COOH (D) CH 3 – CH – COOH
CH3
ORGANIC CHEMISTRY
9. The reaction of phenol with benzoyl chloride to give phenyl benzoate is known as :
[IIT-JEE Mains (Online)2013]
(A) Schotten - Baumann reaction (B) Reimer - Tiemann reaction
(C) Claisen reaction (D) Gatterman-Koch reaction
10. Phenol on heating with CHCl3 and NaOH gives salicylaldehyde. The reaction is called :
(A) Claisen reaction (B) Hell - Volhard - Zelinsky reaction
(C) Cannizzaro’s reaction (D) Reimer - Tiemann reaction
11. Carbylamine forms from aliphatic or aromatic primary amine via which of the following intermediates ?
(A) Carbene (B) Carbon radical (C) Carbo cation (D) Carbanion
12. Which one of the following reactions will not result in the formation of carbon bond ?
[IIT Mains Online 2014]
(A) Reimer-Tieman reaction (B) Friedel Craft's acylation
(C) Wurtz reaction (D) Cannizzaro reaction
13. In the Hofmann bromamide degradation reaction , the number of moles of NaOH and Br2 used per mole
of amine produced are : [JEE MAIN 2016]
(A) One mole of NaOH and one mole of Br2. (B) Four moles of NaOH and two moles of Br2.
(C) Two moles of NaOH and two moles of Br2.(D) Four moles of NaOH and one mole of Br2.
14. In the Hofmann bromamide degradation reaction, the number of moles of NaOH and Br2 used per mole
of amine produced are : [IIT-JEE Mains 2016]
(A) One mole of NaOH and one mole of Br2.
(B) Four moles of NaOH and two moles of Br2.
(C) Two moles of NaOH and two moles of Br2.
(D) Four moles of NaOH and one mole of Br2.
15. p-cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cya-
nide to form, the compound B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure
of the carboxylic acid is [AIEEE-2005]
CH3 CH3
CH(OH)COOH
(A) (B)
CH(OH)COOH
OH OH
CH3 CH3
CH2COOH
(C) (D)
CH2COOH
OH OH
ORGANIC CHEMISTRY
16. Which one of the following methods is neither meant for the synthesis nor for separation of amines?
(A) Hinsberg method (B) Hofmann method [AIEEE-2005]
(C) Wurtz reaction (D) Curtius reaction
17. Sodium phenoxide when heated with CO2 under pressure at 125ºC yields a product which on acetylation
produces C.
ONa 125 º H 
 B 
+ CO2 5Atm  C
Ac O 2
The major product C would be [JEE MAINS-2014]

OH
OH O–COCH3 O–COCH3
COCH3
(A) (B) COOCH3 (C) (D) COOH
COOH
COCH3
18. Consider the reaction sequence below : [JEE MAINS ONLINE-2016]

OCH3
Succinic anhydride Clemmenson's

A
AlCl3 reduction
X is :
OH OCH3 OH
OCH3
H3CO H3CO
(A) (B) (C) (D)
OH
OH
19. Phenol on treatment with CO2 in the presence of NaOH followed by acidification produces compound
X as the major product. X on treatment with (CH3CO)2O in the presence of catalytic amount of H2SO4
produces
[JEE MAINS OFFLINE-2018]
O
CO2H O O CH3 O O CH3

C
O CH3 O
OH
(A) (B) (C) (D)
CO2 H
CH3 CO2H
O
CO2H
ORGANIC CHEMISTRY
20. p-hydroxybenzophenone upon reaction with bromine in carbon tetrachloride gives
O O
Br
Br
(A) (B)
HO HO
O Br O
Br
(C) (D)
HO HO
21. The organic compound that gives following qualitative analysis is [JEE MAINS ONLINE-2019]
Test Inference
(i) Dil. HCl Insoluble
(ii) NaOH solution Soluble
(iii) Br2/water Decolourisation
OH OH
NH2 NH2
(A) (B) (C) (D)
22. The major product of the following reaction is [JEE MAINS ONLINE-2019]
OH
Br2(excess)
SO3H
OH OH
Br
(A) (B)
Br Br
Br SO3H
OH OH
Br Br Br Br
(C) (D)
Br SO3H
ORGANIC CHEMISTRY
23. The major product of the following reaction is [JEE MAINS ONLINE-2019]
CH3
OH
(i)aq.NaOH
(ii)CH3 l
CH3 CH3
OH OH
(A) (B)
CH3 CH3
CH3
CH3 OH
OCH3
(C) (D)
CH3
24. The increasing ordered of the pKa values of the following compound is
OH OH OH OH
NO2
NO2 OMe
A B C D
(A) D < A < C < B (B) B < C < A < D (C) C < B < A < D (D) B < C < D < A
25. A solution of phenol in chloroform when treated with aqueous NaOH gives compound P as a major
product. The mass percentage of carbon in P is_______. (to the nearest integer)
(Atomic mass : C = 12; H = 1; O = 16) [JEE MAINS ONLINE-2020]
[JEE-ADVANCED]
1. Acetamide is treated separately with the following regents. Which of these would give methylamine?
[JEE 1983]
(A) PCl5 (B) Sodalime (C) NaOH + Br2 (D) Hot, conc. H2SO4
2. Carbylamine test is performed in alc. KOH by heating a mixture of [JEE 1984]

(A) chloroform and silver powder
(B) trihalogenated methane and a primary amine
(C) an alkyl halide and a primary amine
(D) an alkyl cyanide and a primary amine
ORGANIC CHEMISTRY
PREVIOUS YEARS QUESTIONS Phenol & Aniline (Carbene & Nitrene Mechanism Based)
3. When phenol is reacted with CHCl3 and NaOH followed by acidification, salicyladehyde is formed.
Which of the following species are involved in the above mentioned reaction as intermediates ?
–
[JEE 1995]
O OH O O
H CHCl2 H CH2Cl
(A) CCl2 (B) (C) CHCl (D)
OH
4. CH3NH2 + CHCl3 + KOH  Nitrogen containing compound + Cl + H2O. Nitrogen containing

compound is [JEE 2006]
–   –
(A) CH3CN (B) CH3NHCH3 (C) CH3 – N  C (D) CH3 – N  C
AlCl3 (i) O2 / 
5. + Cl – CH2CH2 – CH3 P + Q + Phenol [JEE 2006]
(ii) H3O
P and Q are respectively
(A) + CH3CH2CHO (B) + CH3COCH3
(C) + CH3COCH3 (D) + CH3CH2CHO
Comprehension (Q.6 to Q.8) [JEE-2006]

RCONH2 is converted into RNH2 by means of Hofmann bromamide degradation.
O O O
Cl  Cl  Cl
NH2 NH–Br –
..N – Br
(i) (ii) (iii)
–
OK+ O
O C
H2N Cl  N Cl  N Cl
H
(vi) (v) (iv)
In this reactin, 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.
ORGANIC CHEMISTRY
6. How can the conversion of (i) to (ii) be brought about?

(A) KBr (B) KBr + CH3ONa (C) KBr + KOH (D) Br2 + KOH
7. Which is the rate determining step in Hofmann bromamide degradation?

(A) Formation of (i) (B) Formation of (ii) (C) Formation of (iii) (D) Formation of (iv)
8. What are the constituent amines formed when the mixture of (i) and (ii) undergoes Hofmann bromamide
degradation ?
15
CONH2 CONH2
D (i) (ii)
15
NH2 NH2 15
(A) , , NH2 , NH2
D D
NH2 15 15 15
(B) , NH2 (C) NH2 , NH2
D
15
(D) NHD ,
Question No.9 to 11 (3 questions) :

Reimer-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 salicyladehydes as depicted below.
OH ONa OH
CHO CHO
[I] aq. HCl
[JEE 2007]
CH3 CH3 CH3
(I) (II) (III)
9. Which one of the following reagents is used in the above reaction ?

(A) aq NaOH + CH3Cl (B) aq NaOH + CH2Cl2
(C) aq NaOH + CHCl3 (D) aq NaOH + CCl4
10. The electrophile in this reaction is

(A) :CHCl (B) +CHCl2 (C) :CCl2 (D) .CCl3
11. The structure of the intermediate I is
ONa ONa ONa ONa

CH2Cl CHCl2 CCl3 CH2OH
(A) (B) (C) (D)
CH3 CH3 CH3 CH3
ORGANIC CHEMISTRY
12. In the reaction [JEE 2010]

O (1) NaOH/Br2
CH3 C T
O
NH2 (2) C
Cl
the structure of the product T is
O
(A) CH3 C O (B) NH
NH – C C CH3
O
(C) CH3 NH (D) CH3 C O

C NH – C
O
Multiple Choice Questons :

13. A new carbon-carbon bond formation is possible in [JEE 1998]
(A) wolf-kishner reduction (B) Friedel-Craft alkylation

(C) Clemmensen reduction (D) Reimer-Tiemann reaction
14. A positive carbylamine test is given by [JEE 1999]
(A) N, N-dimethylaniline (B) 2,4-dimethylaniline
(C) N-methyl-o-methylaniline (D) p-methylbenzylamine
15. In the following reaction, the product(s) formed is(are) [IIT-JEE Advance 2013]
OH
CHCl3
– ?
OH
CH3
OH O OH OH
OHC CHO CHO
CH3 H3C CHCl2 H3C CHCl2 CH3

P Q R S
(A) P (major) (B) Q (minor) (C) R (minor) (D) S (major)
ORGANIC CHEMISTRY
16. The correct statement(s) about the following reaction sequence is(are) [JEE ADVANCE 2016]
(i) O2 CHCl3/NaOH
Cumene (C9H12) + (P) (Q)(major) + (R)(minor) (Q) NaOH (S)
(ii) H3O PhCH2Br
(A) R is steam volatile

(B) Q gives dark violet coloration with 1% aqueous FeCl3 solution
(C) S gives yellow precipitate with 2,4-dintriophenylhdrazine.
(D) S gives dark violet coloration with 1% aqueous FeCl3 solution.

(i)NaOH H /H O Al O3
17. Phenol    A   2
 B 2  C
CH COOH,  3
(ii ) CO2 / 140C ( esterifica tion )
In this reaction, the end product C is:

(A) salicylaldehyde (B) salicylic acid
(C) phenyl acetate (D) aspirin
18. Column I Column II

O O
(A) – (P) NaOH + Br2
O + CHBr3
O OH
(B) (Q) KOBr
O
(C) R – C – NH2 R – NH2 (R) LiAlH4
O
(D) R – C – NH2 R – CH2 – NH2 (S) DIBAL – H
Match the Column :
19. Column-I Column-II [IIT 2009]
(A) CH3CH2CH2CN (P) Reduction with Pd – C/H2
(B) CH3CH2OCOCH3 (Q) Reduction with SnCl2/HCl
(C) CH3 – CH = CH – CH2OH (R) Development of foul smell on treatment
with chloroform and alcoholic KOH
(D) CH3CH2CH2CH2NH2(s) (S) Reduction with diisobutylaluminium hydride
(DIBAL-H)
(T) Alkaline hydrolysis
ORGANIC CHEMISTRY
O
||
KOH Ph Cl OH CHCl3
20. NH ( A ) (B) (C) (D)
H2O KOH major product
||
O
Structure of (D) is :
(A) Ph – CH2NH2 (B) Ph – NC (C) PhCH2NC (D) PhCH2CN
21. Consider the reaction sequence from P to Q shown below. The overall yield of the major product Q
from P is 75%. What is the amount in grams of Q obtained from 9.3 mL of P ? (Use density of P = 1.00
g mL–1 ; Molar mass of C = 12.0, H= 1.0, O=16.0 and N = 14.0 g mol–1)
[JEE-Advanced 2020]
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. C 2. A 3. D 4. B 5. D 6. A 7. A
8. A 9. A 10. D 11. A 12. D 13. D 14. D
15. B 16. C 17. D 18. B 19. B 20. C 21. B
22. C 23. C 24. B 25. 69
[JEE-ADVANCED]
1. C 2. B 3. A 4. D 5. C 6. D 7. D
8. B 9. C 10. C 11. B 12. C 13. BD 14. BD
15. BD 16. BC or BCD 17. D
18. A  PQ ; B  R ; C  PQ ; D  R;
19. (A)  QST, (B)  ST, (C)  P, (D)  R 20. B 21. 18.6
ORGANIC CHEMISTRY
PRACTICAL ORGANIC CHEMISTRY

[JEE-MAIN / AIEEE]
1. Match the catalysts to the correct processes: [JEE Main 2015]
Catalyst Process
(A) TiCl3 (i) Wacker process
(B) PdCl2 . (ii) Ziegler -Natta Polymerization
(C) CuCl2 (iii) Contact process
(D)V2O5 (iv) Deacon’s process
(A) (A) -{ii), (B) -(iii), (C) -(iv), (D) -(i) (B) (A) -(iii), (B) -(i), (C) -(ii), (D) -(iv)
(C) (A) -(iii), (B) -(ii), (C) -(iv), (D) -(i) (D) (A) -(ii), (B) -(i), (C) -(iv), (D) -(iii)
2. The distillation technique most suited for separating glycerol from spent-lye in the soap industry is :
(A) Distillation under reduced pressure (B) Simple distillation [JEE Main 2016]
(C) Fractional distillation (D) Steam distillation
3. Which of the following compounds will be suitable for Kjeldahl's method for nitrogen estimation?
+ –
NO2 N2Cl NH2
(A) (B) (C) (D)
N
[JEE Main 2018]
4. Two compounds A and B with same molecular formula (C3H6O) undergo Grignard reaction with
methylmagnesium bromide to give products C and D. Products C and D show following chemical tests.
Test C D
Ceric ammonium nitrate Test Positive Positive
Tubridity obtained after
Lucas Test Turbidity obtained immediately
five minutes
Iodoform Test Positive Negative
C and D respectively are: [JEE Main (Online) 2020]
(A)
(B)
(C)
(D)
ORGANIC CHEMISTRY
5. In as estimation of bromine by Carius method, 1.6 g of an organic compound gave 1.88 g of AgBr.
The mass percentage of bromine in the compound is......... [JEE Main (Online) 2020]
(Atomic mass, Ag = 108, Br = 80 g mol–1)
6. Match the following : [JEE Main (Online) 2020]
Test /Method Reagent
(i) Lucas Test (a) C6H5SO2Cl / aq. KOH
(ii) Dumas method (b) HNO3 / AgNO3
(iii) Kjeldahl's method (c) CuO / 
(iv) Hinsberg Test (d) Conc. HCl and ZnCl2
(e) H2SO4
(A) (i)-(d), (ii)-(c), (iii)-(b), (iv)-(e) (B) (i)-(d), (ii)-(c), (iii)-(e), (iv)-(a)
(C) (i)-(b), (ii)-(a), (iii)-(c), (iv)-(d) (D) (i)-(b), (ii)-(d), (iii)-(e), (iv)-(a)
[JEE-ADVANCED]
1. 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 OMR. [JEE 2007]
Column I Column II
(A) C6H5CHO (P) gives precipitate with
2,4-dinitrophenylhydrazine
(B) CH3CCH (Q) gives precipitate with AgNO3
(C) CN – (R) is a nucleophile
(D) I– (S) is involved in cyanohydrin formation
2. 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 OMR.
Column I Column II [JEE 2008]
+ -
(A) H2N – NH3Cl (P) sodium fusion extract of the compound gives
Prussian blue colour with FeSO4
+ -
NH3I
(B) HO (Q) gives positive FeCl3 test
COOH
+ -
(C) HO NH3Cl (R) gives white precipitate with AgNO3
+ -
(D) O2N NH – NH3Br (S) reacts with aldehydes to form the corresponding
hydrazone derivative
NO2
3. An organic compound (C8H10O2) 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 ?
[JEE Advanced 2020]
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. D 2. A 3. D 4. A 5. 50.00 6. B
[JEE-ADVANCED]
1. (A) P, S; (B) Q; (C) Q, R, S; (D) Q,R 2. (A) R,S (B) P,Q (C) P,Q,R (D) P,S
3. 6
ORGANIC CHEMISTRY
BIOMOLECULES
[JEE-MAIN / AIEEE]
1. RNA contains - [AIEEE-2002]
(A) Urasil, Ribose (B) Thiamine, Ribose
(C) Cytocine, Deoxyribose (D) Adenine, Deoxyribose
2. Complete hydrolysis of cellulose gives – [AIEEE-2003]
(A) D-glucose (B) L-glucose (C) D-fructose (D) D-ribose
3. The reason for double helical structure of DNA is operation of – [AIEEE-2003]
(A) Hydrogen bonding (B) Electrostatic attractions
(C) vander Waal’s forces (D) Dipole-dipole interaction
4. Coordination compounds have great importance in biological systems, In this context which of the following
statements is incorrect ? [AIEEE-2004]
(A) Chlorophylls are green pigments in plants and contain calcium
(B) haemoglobin is the red pigment of blood and contains iron
(C) Cyanocobalamin is B12 and contains cobalt
(D) Carboxypeptidase–A is an enzyme and contains zinc
5. Which base is present in RNA but not in DNA ? [AIEEE-2004]
(A) Uracil (B) Cytosine (C) Guanine (D) Thymine
6. Insulin production and its action in human body are responsible for the level of diabetes. This compound
belongs to which of the following categories ? [AIEEE-2004]
(A) A co-enzyme (B) A hormone (C) An enzyme (D) An antibiotic
7. Identify the correct statement regarding enzymes : [AIEEE-2004]
(A) Enzymes are specific biological catalysts that can normally function at very high temperatures
(T~ 1000 K)
(B) Enzymes are normally heterogeneous catalysts that are very specific in their action
(C) Enzymes are specific biological catalysts that cannot be poisoned
(D) Enzymes are specific biological catalysts that possess well-defined active sites
8. In both DNA and RNA, heterocylic base and phosphate ester linkages are at – [AIEEE-2005]
(A) C2' and C5' respectively of the sugar molecule
(B) C5' and C2' respectively of the sugar molecule
(C) C5' and C1' respectively of the sugar molecule
(D) C1' and C5' respectively of the sugar molecule
9. The pyrimidine bases present in DNA are – [AIEEE 2006]
(A) cytosine and guanine (B) cytosine and thymine
(C) cytosine and uracil (D) cytosine and adenine
10. The term anomers of glucose refers to – [AIEEE 2006]
(A) a mixture of (D)-glucose and (L)-glucose
(B) enantiomers of glucose
(C) isomers of glucose that differ in configuration at carbon one (C-1)
(D) isomers of glucose that differ in configurations at carbons one and four (C-1 and C-4)
ORGANIC CHEMISTRY
11. The secondary structure of a protein refers to – [AIEEE 2007]
(A) -helical backbone (B) hydrophobic interactions
(C) sequence of -amino acids (D) fixed configuration of the polypeptide backbone
12. -D-(+)-glucose and -D-(+)-glucose are [AIEEE 2008]

(A) epimers (B) anomers (C) enantiomers (D) conformers
13. The two functional groups present in a typical carbohydrate are : [AIEEE 2009]
(A) – OH and –COOH (B) – CHO and –COOH
(C) > C = O and –OH (D) – OH and –CHO
14. Which of the following compounds can be detected by Molisch's test ? [AIEEE 2012]
(A) Amines (B) Primary alcohols (C) Nitro compounds (D) Sugars
15. Which one of the following statement is correct? [AIEEE 2012]

(A) All amino acids except glycine are optically active.
(B) All amino acids except glutamic acid are optically active.
(C) All amino acids except lysine are optically active.
(D) All amino acids are optically active.
16. Synthesis of each molecule of glucose in photosynthesis involves: [JEE Main 2013]
(A) 10 molecules of ATP (B) 8 molecules of ATP
(C) 6 molecules of ATP (D) 18 molecules of ATP
17. Which one of the following bases is not present in DNA? [JEE Main 2014]
(A) Adenine (B) Cytosine (C) Thymine (D) Quinoline
18. Thiol group is present in : [JEE Main 2016]

(A) Methionine (B) Cytosine (C) Cystine (D) Cysteine
19. Which of the following compounds will behave as a reducing sugar in an aqueous KOH solution ?
[JEE Main 2017]
HOH2C O CH2OH HOH2C O CH2OH

HO HO
(A) (B) OCH3
OH OH
HOH2C
HOH2C O CH2OH
O CH2OCH3
OH HO
(C) (D) OCOCH3
OH
OH OH
20. Glucose on prolonged heating with HI gives: [JEE Main 2018]

(A) Hexanoic acid (B) 6-iodohexanal (C) n-Hexane (D) 1-Hexene
ORGANIC CHEMISTRY
21. Which of the given statements in incorrect about glycogen ? [JEE Mains 2019]
(A) It is straight chain polymer similar to amylose
(B) Only -linkages are present in the molecule
(C) It is present in animal cells
(D) It is present in some yeast and fungi
22. Which of the following statement is not true about RNA? [JEE Mains 2019]
(A) It controls the synthesis of protein
(B) It has always double stranded -helix structure
(C) It usually does not replicate
(D) It is present in the nucleus of the cell
23. Number of stereo-centres present in linear and cyclic structures of glucose are respectively
[JEE Mains 2019]
(A) 4 and 5 (B) 4 and 4 (C) 5 and 4 (D) 5 and 5
24. Amylopectin is composed of [JEE Mains 2019]

(A) -D-glucose, C1-C4 and C2-C6 linkages (B) -D-glucose, C1-C4 and C2-C6 linkages
(C) -D-glucose, C1-C4 and C1-C6 linkages (D) -D-glucose, C1-C4 and C1-C6 linkages
25. The peptide that gives positive ceric ammonium nitrate and carbylamine tests is [JEE Mains 2019]
(A) Lys-Asp (B) Ser-Lys (C) Gln-Asp (D) Asp-Gln
26. Which of the following statement is not true about sucrose ? [JEE Mains 2019]
(A) It is also named as invert sugar
(B) The glycosidic linkage is present between C1 of -glucose and C1 of -fructose
(C) It is a non-reducing sugar
(D) On hydrolysis, it produces glucose and fructose
27. Fructose and glucose can be distinguished by [JEE Mains 2019]

(A) Fehling’s test (B) Barfoed’s test (C) Benedict’s test (D) Seliwanoff’s test
28. Maltose on treatment with dilute HCl gives [JEE Mains 2019]
(A) D-glucose and D-fructose (B) D-fructose
(C) D-galactose (D) D-glucose
29. Which of the following tests cannot be used for identifying amino acids ? [JEE Mains 2019]
(A) Barfoed test (B) Ninhydrin test (C) Xanthoproteic test (D) Biuret test
30. The increasing order of pKa of the following amino acids in aqueous solution is Gly, Asp, Lys, Arg
(A) Asp < Gly < Arg < Lys (B) Arg < Lys < Gly < Asp [JEE Mains 2019]
(C) Gly < Asp < Arg < Lys (D) Asp < Gly < Lys < Arg
PREVIOUS YEARS QUESTIONS ORGANICBiomolecules
CHEMISTRY
31. Consider the following reactions : [JEE Mains 2020]
x.eq.of
(i) Glucose + ROH 
dry HCl
 Acetal 
(CH3CO)2 O
 acetyl derivative
Ni/H2 y eq.of
(ii) Glucose   A 
(CH3CO)2 O
z eq.of
(iii) Glucose 
(CH3CO)2 O
'x', 'y' and 'z' in these reactions are respectively :

(A) 5, 6 & 6 (B) 4, 5 & 5 (C) 4, 6 & 5 (D) 5, 4 & 5
32. The correct observation in the following reaction is: [JEE Mains 2020]
(A) Formation of blue colour (B) Formation of violet colour

(C) Formation of red colour (D) Gives no colour
33. The number of groups present in a tripeptide Asp–Glu-Lys is [JEE Mains 2020]
34. What are the functional groups present in the structure of maltose ? [JEE Mains 2020]
(A) Two acetals (B) One acetal and one ketal
(C) One ketal and one hemiketal (D) One acetal and one hemiacetal
35. Which of the following is not an essential amino acid ? [JEE Mains 2020]
(A) Tyrosine (B) Valine (C) Leucine (D) Lysine
36. The number of chiral carbon(s) present in peptide, IIe-Arg-Pro, is ........ . [JEE Mains 2020]
37. The number of chiral carbons present in sucrose is........... [JEE Mains 2020]
38. Which one of the following statement is not true ? [JEE Mains 2020]
(A) Lactose contains -glycosidic linkage between C1 of galactose and C4 of glucose
(B) On acid hydrolysis, lactose gives one molecule of D(+) - glucose and one molecule of
D(+)-galactose.
(C) Lactose is a reducing sugar and it gives Fehling's test.
(D) Lactose (C11H22O11) is a disaccharide and it contains 8 hydroxyl groups.
ORGANIC CHEMISTRY
[JEE-ADVANCED]
1. Give the structures of the products in each of the following reactions. [JEE 2000]

Sucrose H A + B
2. Aspartame, an artificial sweetener, is a peptide and has the following structure: [JEE 2001]
CH 2  C6 H 5
|
H 2 N  CH  CONH  CH  COOCH 3
|
CH 2  COOH
(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?
3. Following two amino acids lysine and glutamine form dipeptide linkage. What are two possible dipeptides?
NH2 NH2
H2N COOH + HOOC COOH [JEE 2003]
4. The structure of D-Glucose is as follows- [JEE 2004]

CHO
H OH
HO H
H OH
H OH
HO
(a) Draw the structure of L -Glucose
(b) Give the reaction of L - Glucose with Tollen's reagent.
5. Which of the following pairs give positive Tollen’s test? [JEE 2004]
(A) Glucose, sucrose (B) Glucose, fructose
(C) Hexanal, Acetophenone (D) Fructose, sucrose
6. Two forms of D – glucopyranose, are called. [JEE 2005]

(A) Enantiomers (B) Anomers (C) Epimers (D) Diastereomers
7. When benzene sulphonic acid and p-nitrophenol are treated with NaHCO3, the gases released
respectively are [JEE 2006]
(A) SO2, NO2 (B) SO2, NO (C) SO2, CO2 (D) CO2, CO2
8. Statement-1 : Glucose gives a reddish-brown precipitate with Fehling’s solution.

because [JEE 2007]
Statement-2 : Reaction of glucose with Fehling’s solution gives Cu2O and gluconic acid.
ORGANIC CHEMISTRY
9. 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.
10. 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
11. Cellulose upon acetylation with excess acetic anhydride / H2SO4 (catalytic) gives cellulose triacetate
whose structure is AcO [JEE 2008]
H O O–
H
AcO
OAc H
H O O H
AcO H
OAc H H OAc
H H O O H
(A) OAc H H OAc
–O H
AcO
H OAc
H O O–
H
AcO
OH H
H O O H
AcO H
OH H H OH
O O
H H H
OH H H OH
(B) – O H
H OH
AcO AcO AcO
H H O H H O H H
H O O–
OAc H H
OAc H OAc H
–O O O H
(C) H OAc H OAc H OAc
AcO AcO AcO
H H O H H O H H
H O O–
H
H H H H
– O O H H
(D) O H
OAc OAc OAc OAc OAc OAc
ORGANIC CHEMISTRY
12. The correct statement(s) about the following sugars X and Y is(are) [JEE 2009]
CH2OH CH2OH
O O
H H HOH2C O H CH2OH H H
H H
OH H O O H HO
H HO H O OH
HO CH2OH H
H OH OH H OH H
OH H HO H
H OH
(X)
(Y)
(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  and  , respectively.
(D) The glucosidic linkages in X and Y are  and  , respectively.
13. Among cellulose, poly vinyl chloride, nylon and natural rubber, the polymer in which the intermolecular
force of attraction is weakest in [JEE 2009]
(A) Nylon (B) Poly vinyl chloride
(C) Cellulose (D) Natural Rubber
14. The correct statement about the following disaccharide is [JEE 2010]
CH2OH
O H CH2OH O
H H
H
OH H H HO
OH CH 2OH
OCH 2CH2O
H OH OH H
(a) (b)
(A) Ring (a) is pyranose with -glycosidic link.
(B) Ring (a) is furanose with -glycosidic link
(C) Ring (b) is furanose with -glycosidic link
(D) Ring (b) is pyranose with -glycosidic link
15. The following carbohydrate is [JEE 2011]
(A) a ketohexose (B) an aldohexose (C) an -furanose (D) an -pyranose
16. 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]
ORGANIC CHEMISTRY
17. The substituents R1 and R2 for nine peptides are listed in the table given below. How many of these
peptides are positively charged at pH = 7.0 ? [JEE 2012]
 
H 3 N  C H  CO  NH  C H  CO  NH  C H  CO  NH  C H  CO O
| | | |
H R1 R2 H
Peptide R1 R2
I H H
II H CH 3
III CH 2COOH H
IV CH 2CONH2 (CH 2 ) 4 NH 2
V CH 2CONH2 CH 2CONH 2
VI (CH 2 ) 4 NH 2 (CH 2 ) 4 NH 2
VII CH 2COOH CH 2CONH 2
VIII CH 2OH (CH 2 ) 4 NH 2
IX (CH 2 ) 4 NH 2 CH 3
18. When the following aldohexose exists in its D-configuration, the total number of stereoisomers in its
pyranose form is [JEE 2012]
CHO
|
CH 2
|
CHOH
|
CHOH
|
CHOH
|
CH 2OH
19. 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 Advance 2013]
20. The total number of distinct naturally occuring amino acids obtained by complete acidic hydrolysis
of the peptide shown below is [JEE Advance 2014]
O
O O H O H O H
N
N N N
N N N
H
N CH2 O H O H CH2 O
O
ORGANIC CHEMISTRY
21. The structure of D- (+) glucose is : [JEE Advance 2015]
CHO
H OH
HO H
H OH
H OH
CH 2 OH
The structure of L-(–) glucose is :
CHO CHO CHO CHO

HO H H OH HO H HO H
H OH HO H HO H HO H
HO H H OH H OH HO H
(A) (B) HO (C) HO (D)
HO H H H H OH
CH 2 OH CH 2 OH CH 2 OH CH 2 OH
22. For 'invert sugar', the correct statement(s) is (are) [JEE Advance 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 catalysed hydrolysis of maltose
(B) 'invert sugar' is an equimolar mixture of D-(+)-glucose and D-(–)-fructose
(C) specific rotation of 'invert sugar' is –20°
(D) on reaction with Br2 water, 'invert sugar' forms saccharic acid as one of the products
23. The Fischer presentation of D-glucose is given below. [JEE Advance 2018]
CHO
H OH
HO H
H OH
H OH
CH2OH
D-glucose
The correct structure(s) of -L-glucopyranose is (are)
ORGANIC CHEMISTRY
H H
O O
HO CH2 OH OH HO CH2 OH OH
(A) H H HO H (B) H H H H
OH H OH OH
CH2OH H
O O
H H OH HO CH2OH H
(C) HO OH HO H (D) H H HO OH
H H OH H
24. Which of the following statements(s) is (are) true ? [JEE Advanced 2019]
(A) Oxidation of glucose with bromine water gives glutamic acid
(B) The two six-membered cyclic hemiacetal forms of D-(+)-glucose are called anomers
(C) Monosaccharides cannot be hydrolysed to give polyhydroxy aldehydes and ketones
(D) Hydrolysis of sucrose gives dextrorotatory glucose and laevorotatory fructose
25. The structure of a peptide is given below : [JEE Advanced 2020]
If the absolute values of the net charge of the peptide at pH = 2, pH = 6, and pH = 11 are |z1|, |z2|, and
|z3|, respectively, then what is |z1| + |z2| + |z3|?
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. A 2. A 3. A 4. A 5. A 6. B 7. D
8. D 9. B 10. C 11. A 12.  13. C 14. D
15. A 16. D 17. D 18. D 19. D 20. C 21. A
22. B 23. A 24. D 25. B 26. B 27. D 28. D
29. A 30. D 31. C 32. C 33. 5 34. 4 35. A
36. 4 37. 9 38. A
[JEE-ADVANCED]
CH2OH
CHO
CHO
H OH
OH C=O
HO H
1. + HO H
H OH
OH H OH
H OH
OH H OH
CH2OH CH2OH
Glucose Frucose
2. (i) Amine, carboxylic acid, Amide, Ester

O
NH–C COOH
3. H2N COOH
NH2 O
HOOC NH–C COOH
CHO COO
HO H HO H
+
H OH [Ag(NH3)2] H OH
4. HO H HO H
HO H HO H
HO HO
L - Glucose
5. B 6. B 7. D 8. A 9. D
10. (A) P,S; (B) Q, R; (C) P, R; (D) PRS 11. A 12. BC 13. D 14. A
15. B 16. 6 17. 4 18. 8 19. 4 20. 1 21. A
22. BC 23. D 24. BCD 25. 5
ORGANIC CHEMISTRY
POLYMER
[JEE-MAIN / AIEEE]
1. Monomers are converted to polymer by – [AIEEE-2003]
(A) Hydrolysis of monomers
(B) Condensation reaction between monomers
(C) Protonation of monomers
(D) None is correct
2. Nylon threads are made of – [AIEEE-2003]

(A) Polyamide polymer (B) Polyethylene polymer
(C) Polyvinyl polymer (D) Polyster polymer
3. Which of the following is a polyamide ? [AIEEE-2005]

(A) Nylon-66 (B) Teflon (C) Bakelite (D) Terylene
4. Which of the following is fully fluorinated polymer- [AIEEE-2005]

(A) Teflon (B) Neoprene (C) PVC (D) Thiokol
5. Bakelite is obtained from phenol by reacting with [AIEEE 2008]

(A) CH3CHO (B) CH3COCH3 (C) HCHO (D) (CH2OH)2
6. Buna-N synthetic rubber is a copolymer of - [AIEEE 2009]
Cl
|
(A) H 2 C  CH  C  CH 2 and H2C  CH  CH  CH2
(B) H2C  CH  CH  CH2 and H5 C 6  CH  CH2

(C) H2C = CH – CN and H2C = CH – CH = CH2
(D) H 2 C  CH  CN and H 2 C  CH  C  CH 2
|
CH 3
7. The species which can best serve as an initiator for the cationic polymerization is
[AIEEE 2012]
(A) AlCl3 (B) BuLi (C) LiAlH4 (D) HNO3
8. Which one is classified as a condensation polymer? [JEE Main 2014]

(A) Neoprene (B) Teflon (C) Acrylonitrile (D) Dacron
9. Which polymer is used in the manufacture of paints and lacquers ? [JEE Main 2015]
(A) Polypropene (B) Poly vinyl chloride
(C) Bakelite (D) Glyptal
ORGANIC CHEMISTRY
10. Which of the following statements about low density polythene is FALSE? [JEE Main 2016]
(A) It is used in the manufacture of buckets, dust-bins etc.
(B) Its synthesis requires high pressure.
(C) It is a poor conductor of electricity.
(D) Its synthesis requires dioxygen or a peroxide initiator as a catalyst.
11. The formation of which of the following polymers involves hydrolysis reaction ?
[JEE Main 2017]
(A) Bakelite (B) Nylon 6, 6 (C) Terylene (D) Nylon 6
12. Which of the following polymers is not obtained by condensation polymerisation?

[JEE Main 2020]
(A) Nylon 6, 6 (B) Buna – N (C) Bakelite (D) Nylon 6
13. Consider the Assertion and Reason given below : [JEE Main 2020]
Assertion (A) : Ethene polymerized in the presence of Ziegler Natta Catalyst at high
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 but (R) is not the correct explanation of (A).
(B) Both (A) and (R) are correct and (R) is the correct explanation of (A).
(C) (A) is correct but (R) is wrong.
(D) (A) and (R) both are wrong.
14. The correct match between Item-1 and Item-II is : [JEE Main 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)-(IV), (b)-(III), (c)-(II), (d)-(I) (B) (a)-(III), (b)-(IV), (c)-(III), (d)-(I)
(C) (a)-(IV), (b)-(III), (c)-(I), (d)-(II) (D) (a)-(III), (b)-(IV), (c)-(I), (d)-(II)
ORGANIC CHEMISTRY
[JEE-ADVANCED]
1. Give the structures of the products in each of the following reactions : [JEE 2000]
NOH

H C Polymerisa
 tion  [D]n
2. Monomer A of a polymer on ozonolysis yields two moles of HCHO and one mole of CH3COCHO.
(a) Deduce the structure of A. [JEE 2005]
(b) Write the structure of “all cis” – form of polymer of compound A.
3. On complete hydrogenation, natural rubber produces [JEE Advance 2016]

(A) ethylene-propylene copolymer (B) vulcanised rubber
(C) polypropylene (D) polybutylene
4. Choose the correct option(s) from the following: [JEE Advance 2019]
(A) Cellulose has only -D-glucose units that are joined by glycosidic linkages
(B) Teflon is prepared by heating tetrafluoroethene in presence of a persulphate catalyst at high
pressure
(C) Natural rubber is polyisoprene containing trans alkene units
(D) Nylon-6 has amide linkages
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. B 2. A 3. A 4. A 5. C 6. C 7. A
8. D 9. D 10. A 11. D 12. B 13. B 14. A
[JEE-ADVANCED]
O O O
CH3
Ozonolysis +
CH2
2. (a)
H2C H H H3 C H
A
H3 C H H3C H
CH2 CH2
(b) CH2
CH2
H3C H
3. A
4. BD
ORGANIC CHEMISTRY
CHEMISTRY IN EVERYDAY LIFE

[JEE-MAIN / AIEEE]
1. 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)5NOS]
2. Which one of the following method is neither meant for the synthesis nor for separation of amines ?(A)
Hinsberg method (B) Hofmann method [AIEEE-2005]
(C) Wurtz reaction (D) Curtius reaction
3. Which one of the following types of drugs reduces fever ? [AIEEE - 2005]
(A) Tranquiliser (B) Antibiotic (C) Antipyretic (D) Analgesic
4. The hydrocarbon which can react with sodium in liquid ammonia is : [AIEEE-2008]
(A) CH3CH2 C  CH (B) CH3CH = CHCH3
(C) CH3CH2C  CCH2CH3 (D) CH3CH2CH2C  CCH2CH2CH3
5. Which of the following reagents may be used to distinguish between phenol and benzoic acid ?
[AIEEE-2011]
(A) Aqueous NaOH (B) Tollen's reagent (C) Molisch reagent (D) Neutral FeCl3
6. Aspirin is known as : [AIEEE-2012]

(A) Acetyl salicylic acid (B) Phenyl salicylate
(C) Acetyl salicylate (D) Methyl salicylic acid
7. What is DDT among the following : [AIEEE-2012]

(A) Greenhouse gas (B) A fertilizer
(C) Biodegradable pollutant (D) Non-biodegradable pollutant
8. The gas leaked from a storage tank of the Union Carbide plant in Bhopal gas tragedy was :
(A) Methylisocyanate (B) Methylamine [JEE(Mains)-2013]
(C) Ammonia (D) Phosgene
9. Which of the following is an anionic detergent ? [JEE(Mains)-2016]

(A) Sodium lauryl sulphate (B) Cetyltrimethyl ammonium bromide
(C) Glyceryl oleate (D) Sodium stearate
10. Which of the following is a thermosetting polymer [JEE(Mains)-2019]

(A) Bakelite (B) Buna-N (C) Nylon-6 (D) PVC
ORGANIC CHEMISTRY
11. The correct match 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
temp. and Pressure
C. Novolac III. Ziegler-Natta catalyst
D. Nylon-6 IV. Acid or base catalyst
Codes
A B C D A B C D
(A) III I IV II (B) IV II I III
(C) II IV I III (D) III I II IV
12. Which of the following is a condensation polymer ? [JEE(Mains)-2019]

(A) Nylon-6, 6 (B) Neoprene (C) Teflon (D) Buna-S
13. Noradrenaline is a/an [JEE(Mains)-2019]

(A) antidepressant (B) antithistamine (C) neurotransmitter (D) antacid
O
14. Which of the following compounds is a constituent of the polymer [ HN – C – NH CH 2]n ?
[JEE(Mains)-2019]
(A) N-methyl urea (B) Methylamine (C) Ammonia (D) Formaldehyde
15. The two monomers for the synthesis of nylon 6, 6 are [JEE(Mains)-2019]
(A) HOOC(CH2)4COOH, H2N(CH2)4 NH2 (B) HOOC(CH2)6COOH, H2N(CH2)4 NH2
(C) HOOC(CH2)4COOH, H2N(CH2)6 NH2 (D) HOOC(CH2)6COOH, H2N(CH2)6 NH2
16. Poly--hydroxybutyrate-Co--hydroxyvalerate (PHBV) is a copolymer of .....

(A) 3-hydroxybutanoic acid and 2-hydroxypentanoic acid [JEE(Mains)-2019]
(B) 2-hydroxybutanoic acid and 3-hydroxypentanoic acid
(C) 3-hydroxybutanoic acid and 4-hydroxypentanoic acid
(D) 3-hydroxybutanoic acid and 3-hydroxypentanoic acid
17. The antifertility drug ‘’Novestrol’’ can react with : [JEE(Mains)-2020]

(A) ZnCl2 / HCl ; FeCl3 ; Alcoholic HCN (B) Alcoholic HCN ; NaOCl ; ZnCl2 / HCl
(C) Br2 / water, ZnCl2 / HCl ; NaOCl (D) Br2 / water, ZnCl2 / HCl ; FeCl3
18. Glycerol is separated in soap industries by : [JEE(Mains)-2020]
(A) Steam distillation (B) Differential distillation
(C) Fractional distillation (D) Distillation under reduced pressure
ORGANIC CHEMISTRY
19. An ionic micelle is formed on the addition of : [JEE(Mains)-2020]
(A) (excess water to liquid)
(B) liquid diethyl ether to aqueous NaCl solution.
(C) (excess water to liquid)
(D) Sodium stearate to pure toluene

20. Match the following drugs with their therapeutic actions : [JEE(Mains)-2020]
(i) Ranitidine (a) Antidepressant
(ii) Nardil (Phenelzine) (b) Antibiotic
(iii) Chloramphenicol (c) Antihistamine
(iv) Dimetane (Brompheniramine) (d) Antacid
(e) Analgesic
(A) (i)-(a) ; (ii) -(c) ; (iii) -(b) ; (iv) - (e) (B) (i)-(d) ; (ii) -(c) ; (iii) -(a) ; (iv) - (e)
(C) (i)-(d) ; (ii) -(a) ; (iii) -(b) ; (iv) - (c) (D) (i)-(e) ; (ii) -(a) ; (iii) -(c) ; (iv) - (d)
21. If a person is suffering from the deficiency of nor-adrenaline, what king of drug can be suggested ?
[JEE(Mains)-2020]
(A) Antihistamine (B) Analgesic (C) Anti-inflammatory (D) Antidepressant
22. The following molecule acts as an : [JEE(Mains)-2020]
N
(CH2 )2
N
(Brompheniramine)
Br
(A) Anti-depressant (B) Antiseptic (C) Anti-histamine (D) Anti-bacterial
[JEE-ADVANCED]
1. Statement-1 : Aniline on reaction with NaNO2 / HCl at 0ºC followed by coupling with -naphthol
gives a dark blue precipitate. [IIT-JEE 2008]
Statement-2 : The colour of the compound formed in the reaction of aniline with NaNO2/HCl at 0ºC
followed by coupling with -naphthol is due to the extended conjugation.
Statement-1
(D) Statement-1 is False, Statement-2 is True
ORGANIC CHEMISTRY
2. Match the entries in Column I with the correctly related quantum number(s) in Column II.
[IIT-JEE 2008]
Column I Column II
 
(A) H2 N —NH3 Cl (p) sodium fusion extract of the compound gives
Prussian blue colour with FeSO4
NH3I
(B) HO (q) gives positive FeCl3 test
COOH
(C) HO NH3Cl (r) gives white precipitate with AgNO3
(D) O2 N NH—NH3Br (s) reacts with aldehydes to form the corresponding

NO2
hydrazone derivative
3. Amongst the following, the total number of compounds soluble in aqueous NaOH is :
[IIT-JEE 2010]
H3C CH3
N OCH2CH3 OH
CH2OH
NO2 OH CH2CH3 COOH

CH2CH3
N
H3C CH3
(A) 5 (B) 3 (C) 6 (D) 4
4. The compound that does not liberate CO2, on treatment with aqueous sodium bicarbonate solution, is
[JEE(Advanced) 2013]
(A) Benzoic acid (B) Benzenesulphonic acid
(C) Salicylic acid (D) Carbolic acid (Phenol)
ORGANIC CHEMISTRY
ANSWER KEY
[JEE-MAIN/AIEEE]
1. A 2. C 3. C 4. A 5. D 6. A 7. D
8. A 9. A 10. A 11. A 12. A 13. C 14. D
15. C 16. D 17. D 18. D 19. C 20. C 21. D
22. C
[JEE-ADVANCED]
1. D 2. A  r,s ; B  p, q, r ; C  p,q, r, ; D  p, r, s 3. D 4. D

RA Sir JEE PYQ Organic Chemistry

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What are the main topics covered in the document?

What is the IUPAC name of compound CH3COCH(CH3)2 according to the document?

What is the IUPAC name of compound CH3COCH(CH3)2 according to the document?

CONTENT

JEE CRASH COURCE

1. Nomenclature of organic compounds 01 – 07

3. General Organic Chemistry 18 – 31

6. Alcohol & Ether 78 – 95

7. Grignard Reagent 96 – 101

8. Oxidation & Reduction of Organic Compound 102 – 103

9. Carbonyl Compound 104 – 136

10. Carboxylic Acid and its derivative 137 – 151

11. Name Reactions 152 –156

13. Practical Organic Chemistry 168 – 169

14. Biomolecules 170 – 181

15. Polymer 182 – 185

16. Chemistry in Everyday Life 186 – 190

NOMENCLATURE OF ORGANIC COMPOUND

(A) 3,3 -dimethyl-1-hydroxy cyclohexane (B) 1, 1 – dimethyl–3– hydroxy cyclohexane

(A) 6-bromo-2-chlorocyclohexene (B) 3-bromo-1-chlorocyclohexene

5. The IUPAC name of [AIEEE-2007]

(A) 1, 1-diethyl-2-dimethylpentane (B) 4, 4-dimethyl-5, 5-diethylpentane

7. The IUPAC name of neopentane is : [AIEEE -2009]

8. The IUPAC name of compound is :- [AIEEE -2012 (Online)]

(A) 1, 2-Epoxy propane (B) Propylene oxide

9. The IUPAC name of the followig compounds is : [AIEEE -2012 (Online)]

(A) (Z) – 5– hepten – 3 – yne (B) (Z) – 2– hepten – 4 – yne

10. Aspirin is known as : [AIEEE -2012]

(A) 3-bromo-3-methyl-1, 2-dimethylprop-1-ene

16. The IUPAC name for the following compound is : [JEE-Main-2020]

(A) 2,5-dimethyl-6-carboxy-hex-3-enal (B) 2,5-dimethyl-5-carboxy-hex-3-enal

17. The IUPAC name of the following compound is : [JEE-Main-2020]

(A) 3-bromo-5-methylcyclopentane (B) 3-bromo-5-methylcyclopentanoic acid

18. The IUPAC name of the following compound is : [JEE-Main-2020]

(1) 2-nitro-4-hydroxymethyl-5 amino benzaldehyde

(A) 3,3,3-trimethyl-1-propene (B) 1,1,1-trimethyl-2-propene

2. Write the IUPAC name of CH3CH2CH = CHCOOH [JEE 1986]

3. The IUPAC name of the compound CH2=CH–CH(CH3)2 is:

5. Write I.U.P.A.C name of following:

(a) Me = methyl group [JEE 1990]

7. The IUPAC name of C6H5COCl is

8. The IUPAC name of the following compound is [JEE 2009]

9. The correct structure of ethylenediaminetetraacetic acid (EDTA) is [IIT-JEE 2010]

(A) 1-chloro-4-methylbenzene (B) 4-chlorotoluene

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

Pent-2-en-1-oic acid or Pent-2-enoic acid

2. Which of the following does not show geometrical isomerism ? [AIEEE-2002]

3. Racemic mixture is formed by mixing two [AIEEE-2002]

CH3 O CH3 H CH3

6. Which of the following will have meso-isomer also ? [AIEEE-2004]

(A) H3C CH3 (B) H3C

(C) H3C (D)

15. Which one of the following conformation of cyclohexane is chiral? [AIEEE-2007]

(A) S, S (B) R, R (C) R, S (D) S, R

17. The alkene that exhibits geometrical isomerism is : [AIEEE-2009]

19. The IUPAC name of neopentane is : [AIEEE-2009]

25. The product of the reaction given below is : [JEE Mains-2016]

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

26. The absolute configuration of [JEE Mains-2016]