ORGANIC CHEMISTRY

CARBOXYLIC ACIDS AND

IT'S DERIVATIVE ,
ALIPHATIC AMINES

CONTENTS
EXERCISE - I
EXERCISE - II
EXERCISE- III
EXRECISE - IV(A)
EXRECISE - IV(B)
ANSWER KEY
 EXERCISE -I(A)

Q.1 Which one of the following is an acyl group:

O O O
|| || ||
(A) R–O– (B) R  C  O  (C) R  C  (D) R  C  NH 

Q.2 In the given reaction :

O
||
 CHBr3 + [X]
( i ) Br2 / KOH
C 6 H 5  C  CH 3  
(ii ) H 
[X] will be:
(A) C6H5–CHO (B) C6H5COOH (C) C6H5–CH2OH (D) CH3COOH

Q.3 In the reaction sequence :

CH MgBr ( i ) CO
2  (B)
CH3–CC–H 3  CH4+ (A)   
( ii ) H 2 O / H

(B) will be:

(A) CH3–CC–CH3 (B) CH3–CC–MgBr (C) CH3–CC–COOH (D) CH3–CH=CH–COOH

Q.4 Consider the given reaction

Br / 
RCOOAg 2  R–Br
which one of the following acid will give maximum yield of R–Br in the above reaction?
(A) CH  CH  COOH (B) CH3–CH2–CH2–COOH
3
|
CH 3

CH 3
|
(C) CH 3  C  COOH (D) All will give same yield
|
CH 3

Q.5 Benzoic acid on treatment with hydrazoic acid in the presence of concentrated sulphuric acid gives:
(A) Benzamide (B) Sodium benzoate (C) Aniline (D) C6H5CON3

Q.6 The given reaction

C 2H5 C2 H5
| |
N 3H / Conc . H 2SO 4
CH 3  C  COOH       CH 3
 C  NH 2
| |
C3H 7 C 3H 7

is called :
(A) Schmidt reaction (B) Cirtius reaction
(C) Hofmann rearrangement (D) Lossen rearrangement
Q.7 In the given reaction :
CH3–CH2–COOH (
i ) AgNO 3
  [X]
( ii ) Br2 / 

[X] will be:

(A) Ethyl bromide (B) Propyl bromide (C) Propyl propanoate (D) All of these

Q.8 In the reaction sequence:


CH 3  CH  COOH  [Y]
|
OH
[Y] will be:

(A) (B) CH2=CH–COOH

OH
|
(C) CH 2  CH 2  COOH (D)

Q.9 Acetylation reaction with acetyl chloride is carried out in the presence of which solvent?
(A) HOH (B) CH3OH (C) Pyridine (D) NaOH

Q.10 In the reaction:

O
||
C6H5–H [
X]
 C 6 H 5  C  CH 2  C 6 H 5
AlCl3
[X] will be:
(A) C6H5CH2COCl (B) (C6H5–CH2CO)2O
(C) Both (A) and (B) (D) C6H5–CHCl2

Q.11 In the given reaction :

[X] + Acetic anhydride  Aspirin
[X] will be:
(A) Benzoic acid (B) o-methoxybenzoic acid
(C) o-Hydroxybenzoic acid (D) p-Hydroxybenzoic acid

Q.12 The given reaction is :

O
||
C6H5–CHO + C6H5CHO Na [ Fe ( CO ) 4 ]
2    C 6 H 5  C  O  CH 2C 6 H 5
(A) Claissen reaction (B) Tischenko reaction(C) Perkin reaction (D) Cannizzaro reaction
Q.13 In the given reaction:
O O
|| ||
C  CH 3  CH 3  C  OC 2 H 5 C H ONa
2 5
   [X]
C 2 H 5OH

[X] will be:

OH O O
| || ||
C  CH 2  C  CH 3 HC  CH  C  CH 3
(A) (B)
|
H
O O O
|| || ||
(C) CH 3  C  CH 2  C (D) CH 3  C  CH 2  COOH

Q.14 Number of cross products in the given reaction:

CH3COOC2H5 + C6H5–CH2–COOC2H5 C
2 H5ONa
 
C 2 H 5OH

(A) One (B) Three (C) Two (D) four

Q.15 Hofmann degradation is given by:

(A) Imide (B) Acid chloride (C) Acid anhydride (D) None of these

Q.16 In the given reaction:

O
|| LiAlH
C 6H 5  C  N 4  [X]
 

[X] will be:

(A) C6H5–CH2OH (B) C6H5COOH (C) C6H5CONH2 (D) C6H5–CH2–N

Q.17 Which one of the following compounds gives carboxylic acid with HNO2?
O
||
(A) C 6 H 5  C  Cl (B) C6H5CONH2

O O
|| ||
(C) CH 3  C  O  C  CH 3 (D) CH3COOC2H5
Q.18 In the reaction sequence:
O
|| H 2O / H 
CH 3  C  H HCN

   (A)   Product
OH 

Product will be:

OH
|
(A) CH 3  C  COOH
|
H

OH
|
(B) HOOC  C  CH 3
|
H

OH OH
| |
(C) Mixture of CH 3  C  COOH and HOOC  C  CH 3
| |
H H

OH
|
(D) CH 3  CH  CONH 2

Q.19 In the given reaction:

Cl
| ( i ) NH3
CH 3  CH  COOH    [X]
1 mole
( ii ) H 2O
Product [X] will be:
(A) -Amino acid (B) -Aminoamide (C) -Amino acid (D) -Aminoamide

Q.20 Which of the following reactions will give -hydroxy acid as a product:
( i ) NaCN / HCl
(A) CH3–CHO    
( ii ) H 2O / H / 

( i ) Zn
(B) CH3–CHO + Br–CH2–COOC2H5   
( ii ) NH 4Cl / HOH
( iii ) HOH / H  / 

X
|
(C) CH 2  CH 2  COOH NaOH
 /HOH

(D) All of these

Q.21 Rochelle salt is dimetal salt of :

(A) Tartaric acid (B) Citric acid (C) Oxalic acid (D) Salicylic acid
Q.22 In the given reaction :

PCl
3  [X]


[X] will be :

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

Q.23 Sodium bicarbocate reacts with salicylic acid to form:

(A) C6H5ONa (B) (C) (D)

Q.24 In the given reaction :

C
200
  [X]

[X] will be:

(A) Phenyl salicylate (B) Aspirin (C) Phenol (D) Benzoic acid

Q.25 Arrange these esters in decreasing order of ease of esterfication with CH3OH/H :
(I) CH 3  CH  COOH (II) CH 3  CH  CH 2  COOH
| |
CH 3 CH 3

CH 3
|
(III) CH 3  C  COOH (IV) (CH3–CH2)3C–COOH
|
CH 3
(A) II > I > III > IV (B) I > II > III > IV (C) III >IV > II > I (D) IV > III > II > I

Q.26 Arrange following compounds in decreasing order of reactivity for hydrolysis reaction :

(I) C6H5COCl (II) NO2 COCl

O
||
(III) CH3 COCl (IV) OHC C  Cl

(A) II > IV > I > III (B) II > IV > III > I (C) I > II > III > IV (D) IV > III > II > I
Q.27 In the given reaction sequence:

( i ) KMnO / O H /  ( i ) SOCl Br / KOH
CH3–CH2–OH   4    (A)  2  (B) 2  (C)
(ii ) H  ( ii ) NH 3 / 

(C) will be :
(A) Methylamine (B) Eltylamine (C) Propylamine (D) Acetamide
Q.28 Which one of the following on heating gives unsaturated acid:
(A) -Hydroxy acid (B) -Hydroxy acid (C) -Hyroxy acid (D) -Hydroxy acid
Q.29 Which will form lactone on treatment with NaOH ?
(A) -Bromo acid (B) -Bromo acid (C) -Hydroxy acid (D) -Bromo acid
Q.30 Which one of the following will go decarboxylation on heating?
(A) Succinic acid (B) Phthalic acid (C) Malonic acid (D) Adipic acid
Q.31 In the given reaction :
2 ( i ) Br / P
CH3–COOH    [X]
( ii ) NaCN
( iii ) H 2O / H  / 

[X] will be:

(A) CH2 (B) COOH–CH2–CH2–COOH

CH 2  CO
(C) | (D) CH2
CH 2  CO

Q.32 Which optically active compound on reduction with LiAlH4 will give optically inactive compound?
(A) CH 3  CH  COOH (B) CH 3  CH 2  CH  COOH
| |
OCH 3 OH

(C) CH 3  CH 2  CH  COOH (D) CH 3  CH  CH 2  COOH

| |
CH 2 OH OH
Q.33 In the given reaction:
O
||
CH 3  CH  C  CH 2  CH 3 CF COOOH
3   [X] as main product
|
CH 3
[X] will be:
O O
|| ||
(A) CH 3  CH 2  C  O  CH  CH 3 (B) CH 3  CH  C  O  CH 2  CH 3
| |
CH 3 CH 3

O
||
(C) CH 3  C  OC(CH 3 )3 (D) (CH3)3COOCH3
Q.34 Which one of the following reactions can be used for the preparation of -hydroxy acid:
(A) Perkin reaction (B) Reformatsky reaction
(C) Aldol condensation (D) Claisen condensation

Q.35 Which acid can be oxidised be Fehling solution:

(A) Malonic acid (B) Acetic acid (C) Oxalic acid (D) formic acid

Q.36 In the given reaction:

HBr
 [X]

[X] will be:

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

Q.37 Reducing property of formic acid is due to the presence of :

O O
|| ||
(A) – OH (B)  C  H (C)  C  OH (D) All of these
Q.38 In the given reaction:


HOH / H
  [X]

[X] will be:

OH
|
(A) HOOC–CH2–CH2– CH –CH3 (B) CH3–CH2–CH2–CH2–COOH

(C) HO–CH2–CH2–CH2–COOH (D) CH 3  CH 2  CH  CH 2  COOH

|
OH
Q.39 In the given reaction:

LiAlH
4  [A]
 

[B]
[A] and [B] respectively be:

(A) CH 2OH  CH 2  CH 2  CH  CH 2OH and

|
OH

(B) and CH 2OH  CH 2  CH 2  CH  CH 2OH

|
OH

(C) Both are

OH
|
(D) Both are CH 2OH  CH 2  CH 2  CH  CH 2OH

Q.40 In the given reaction:

COOC 2 H 5
+ | Pyridne
  [X]
COOC 2 H 5

[X] will be :

(A) (B)

(C) (D)
Q.41 In the given reaction sequence:
CH 2  COOH
 CH CH NH / 
|  (A) 3 2 2 (B)
CH 2  COOH
(B) will be:

O O
|| ||
(A) CH 2  C  NH  C 2 H 5 (B) CH 2  C
| |
CH 2  C  NH  C 2 H 5 CH 2  C
|| ||
O O
O
||
CH 2  COOH CH 2  C  NH  C 2 H 5
(C) | (D) |
CH 2  COOH CH 2  COOH

Q.42 In the given reaction :

( i ) NaCN / HCl
CH3CHO     (A) Fenton
  (B)
( ii ) H 2O / H /  reagent

(B) will be :
(A) Acetic acid (B) Oxalic acid (C) Pyruvic acid (D) Citric acid

Q.43 In which reaction product is hydrocarbon?

(A) RCOOK Electrolys is 2/
(B) RCOOAg I
   
CH 3
Cl / hv
| C 2 H 5OH
(C) CH3–CH3 2 
 (D) CH 3  C  Cl  
|
CH 3
Q.44 Sodium benzoate on heating with sodalime gives:
(A) Benzene (B) Benzophenone (C) Methane (D) Calcium benzoate

Q.45 Which of the following compounds gives carbondioxide with NaHCO3?

(A) Acetic acid (B) Hexanol (C) Phenol (D) Acetylene

Q.46 When propanoic acid is treated with aqueous sodium bicarbonate, carbon dioxide is liberated. The
carbon of the CO2 comes from :
(A) Methyl group (B) Carboxylic group (C) Methylene group (D) Bicarbonate

Q.47 The reduction of benzoyl chloride with Pd and BaSO4/CaCO3 produces:

(A) Benzyl chloride (B) Benzoic acid (C) Benzaldehyde (D) All of these

Q.48 Which one of the following esters cannot undergo self Claisen condensation?
(A) CH3–CH2–CH2–COOC2H5 (B) C6H5COOC2H5
(C) C6H11–CH2–COOC2H5 (D) C6H5–CH2COOC2H5
Q.49 Amides may be converted into amines by a reaction named after :
(A) Kekule (B) Perkin (C) Hofmann (D) Claisen
Q.50 The treatment of an ester with LiAlH4 followed by acid hydrolysis produces :
(A) Two aldehyde (B) One carboxylic acid and one alcohol
(C) Two alcohols (D) Two acids

Q.51 Which of the following is hydrolysed to give secondary amine:

O
||
(A) Alkyl cyanide (B) H  C  N

(C) Nitro paraffins (D) Acid amide

Q.52 N-Ethyl pthalimide on hydrolysis gives:

(A) Methyl alcohol (B) Ethyl amine (C) Dimethyl amine (D) Diethyl amine

Q.53 Which amine will not react with nitrous acid:

(A) Methyl amine (B) Ethyl amine
(C) Dimethyl amine (D) N, N Dimethyl ethane amine

Q.54 Which gas will be evolved out when [CH3CH2NH2 + (CH3)2CHNH2] is treated with sodium nitrite and
HCl:
(A) Chlorine (B) Ammonia (C) Nitrogen (D) NO2

Q.55 Boiling Ethylamine on reaction with acidified KMnO4 gives:

(A) Acetaldehyde (B) Ethanoic Acid (C) Ethanol (D) Acetamide

Q.56 Methyl amine on reaction with chlorine in the presence of NaOH gives:
(A) Chloroform (B) Methyl chloride
(C) N-Methyl chloramine (D) Chloramine

Q.57 Highest value of pKb will be of:

(A) NH3 (B) (CH3)2NH (C) (CH3)3N (D) CH3NH2

Q.58 Lowest boiling point will be of the compound:

(A) Ethylamine (B) Ethylmethylamine
(C) 1-Propaneamine (D) N,N-Dimethylmethaneamine

Q.59 Amines are basic in nature because:

(A) They produce OH– ions when treated with water
(B) They have replaceable H atoms on N atoms
(C) They have lone pair of electron on N atom
(D) None of these

Q.60 Which of the following diazonium salt is relatively stable of 0-5°C:

(A) CH3–NN}Cl– (B) CH3C(CH3)–NN}Cl–
(C) C6H5–NN}Cl– (D) (CH3)3C–NN}Cl–

Q.61 Alkylamine dissolve in hydrochloric acid to form alkylammonium chloride. The nitrogen in the latter salt is:
(A) Quadricovalent only (B) Tricovalent only
(C) Unielectrovalent only (D) Quadricovalent, Unielectrovalent

Q.62 Which of the following can be detected by carbylamine reaction:

(A) Urea (B) CH3CONH2 (C) C2H5NH2 (D) All of above
Q.63 Cyanides exists in:
(A) Tautomeric form (B) Geometrical form (C) In both form (D) None
Q.64 Hydrolysis of alkyl isocyanide yields:
(A) Primary amine (B) Tert. amine (C) Alcohol (D) Aldehyde
Q.65 Which of the following compound gives the smell of mustard oil:
(A) Alkyl isocyanate (B) Alkyl isothiocyanate
(C) Alkyl isocyanide (D) Alkyl isonitrile
Q.66 The compound obtained by the reaction between primary amine and aldehyde is:
(A) An amide (B) lmine (C) Nitrite (D) Nitro
Q.67 When propionamide reacts with Br2 in the presence of alkali the product is:
(A) CH3CH2CH2NH2 (B) CH3CH2NH2 (C) C3H7CN (D) C2H5CN
Q.68 A reaction of ethyl amine & acetic anhydride leads to the formation of:
(A) CH3NHCOCH3 (B) C2H5CONHCH3 (C) CH3CONHC2H5 (D) CH3–CH=NOC2H5
Q.69 Identify X in the reaction

CHCl / KOH
 3  Intermediate HCl
 X
heat 300 K

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

conc . HCl
Q.70 C=S  A + B
Heat

The unknown compounds A and B in the above reaction are:

(A) Phenyl mercaptan and aniline (B) Thiophenol and aniline hydrochloride
 —  —
(C) C6H5–N=C=S and C 6H 5 NH 3} Cl (D) C6H5CH2SH and C 6H 5 NH 3} Cl

Q.71 Aniline with solid KOH and CS2 gives:

(A) Thiourea (B) Phenyl thio urea (C) Phenol (D) Diphenyl thio urea
O
|| P2O5 CH MgBr
Q.72 C NH 2   W 3  X (
yellow ppt .)
  Y 
Z

 H3 O Ca ( OH ) 2 ,I 2
Z is:
O
||
(A) C  CH 3 (B) COOH

O
||
(C) C (D)
 ( i ) NH , 
3 ( i ) ND ,
Q.73 Y    
(ii ) KOD , Br 
COOH  3 X, What are X and Y:
2 ( ii ) KOH , Br2 

(A) X is NH2; Y is ND2

(B) X is ND2; Y is NH2

(C) both ND2

(D) both NH2

Q.74 Major end product of the following sequence of reaction is:

2 2 Ca ( OH ) ,Cl HNO
CH3CH2CH2CONH2      X 2  Z

(A) CH3CH2CH2NH2 (B) CH3CH2CH2OH
(C) CH 3CHCH 3 (D) CH3CH2COOH
|
OH

Q.75 The bond angles in methane (I), ammonia (II) and trimethyl amine (III) increase in the order:
(A) I > III > II (B) I > II > III (C) II > I > III (D) III > II > I

Q.76 Name the products in the acid-base reaction:

(a) CH3CH2NH2+ HI (b) (CH3)3N + HBr
(A) (a) Trimethyl ammonium iodide (b) Trimethyl ammonium bromide
(B) (a) Ethyl ammonium iodide (b) Methyl ammonium bromide
(C) (a) Ethyl ammonium iodide (b) Trimethyl ammonium bromide
(D) All of these

Q.77 Acetic anhydride and ammonia gives the product:

(A) CH3CONH2 (B) CH3CONHCH3 (C) CH3CN (D) CH3COONH4
Q.78 The artificial sweetener aspartame (A) is converted to _________ on storage for extended periods of
time in aqueous solution:
O O
 || ||
H 3 N  CH  C  NH  CH  C  OCH 3
| |
CH 2 CH 2 Ph
|
CO2 (A )
O O
|| ||
(A) H 2 N  CH  C  NH  CH  C  OCH 3
| |
CH 2 CH 2 Ph
|
CO 2

O O
|| ||
H 2 N  CH  COH  H 2 NCH  COH  CH 3OH
(B) | |
CH 2 CH 2 Ph
|
CO 2 H

(C) + CH3OH

(D) no change, remains as (A)

Q.79 Reductive amination of A forms:

A:

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

Q.80 The synthetic sweetener aspartame, known commercially as Nutra sweet, is carboxylic acid. In aqueous
solution on standing it changes to:

(A) (B)

(C) (D) no hydrolysis is possible

 EXERCISE - I(B)

Q.1 Consider the following statements regarding the following reaction:

( CH 3CO ) 2 O 2 H O
C6H5CHO       C H – CH = CH – COOH + CH COOH
6 5 3
CH 3COONa 

(A) Acetate ion acts as base in this reaction

(B) The anhydride having atleast one -hydrogen, provides an enolate for the reaction
(C) The acetate deprotonates the anhydride to form the nucleophile needed for the reaction
(D) EtONa can also be use as base
Q.2 Which of the following will liberate CO2 on reaction with NaHCO3

(A) OH (B) CH3COOH

CH OH
(C) (D) | 2
CH 2OH

Q.3 RCOOR' can be prepared by:

(A) esterification of RCOOH
(B) esterification of (RCO)2O
(C) Baeyer-Villiger oxidation of RCOR' with peroxy acid
(D) reaction of RCOCl with R'OH

Q.4 In the Hofmann bromamide degradation recation

O
||
R  C  NH 2 + KOH + Br2 
Intermediates are:
(A) RCONHBr (B) RNCO (C) RNH2 (D) None

Q.5 C4H11N + HNO2  C4H10O (3° alcohol)

(X)
hence X will give:
(A) carbyl amine reaction
(B) Hofmann mustard oil reaction
(C) diazonium salt (as the intermediate) with HNO2
(D) base insoluble product with Hinsburg reagent

Q.6 Mixture of 1°, 2° and 3° amines can be separated by:

(A) Hinsberg's method (B) Hofmann's isocyanide test
(C) fractional distillation (D) NaNO2 HCl
Q.7 Which is/are correct reaction(s):

(A) Cl + NH3  + NH4Cl

(B) Cl + 2NH3  NH2+ NH4Cl

(C) Cl + NH3  + NH4Cl

0C
(D) NH2 + HNO2 

Q.8 Which of the following compounds will give acetic acid with KMnO4/H/:
(A) CH3–CHO (B) CH3–CH=CH–CH3
(C) CH3–CC–CH3 (D) CH3CH2OH

Q.9 Acetic acid can be used for the preparation of :

(A) Ethane (B) Methane (C) Acetone (D) ethanol

Q.10 Which one of the following acids will form acetyl chloride with PCl5?
(A) MeCOOH (B) MeCOOMe
(C) MeCOOCOMe (D) Me–CONH2

Q.11 Consider the following reaction:

O O
|| H
||
CH 3  C  OH  CH 3  OH 
 CH 3  C  O  CH 3  HOH
True about the above reaction is:
(A) Product is having smell like fruits
(B) Nucleophilic addition followed by elimination reaction
(C) follows AAC' mechanism
(D) it is irriversible reaction

Q.12 In the given reaction :


RCOOAg + X2  R–X+CO2 + AgX
X2 can be:
(A) Cl2 (B) Br2 (C) I2 (D) F2

Q.13 Which one of the following compounds will give HVZ reaction?

(A) (B)

(C) (D)

Q.14 Sodium salt of which one of the monobasic acids on electrolysis does not give hydrocarbon:
(A) C6H5COOH (B) HCOOH
(C) Me3C–COOH (D) COOH–CH=CH–COOH
Q.15 Which one of the following acids undergoes decarboxylation on strong heating:
(A) Pyruvic acid (B) 3-butenoic acid (C) Formic acid (D) Salicylic acid

Q.16 Which one of the following compounds is least reactive with water?
O O O O
|| || || ||
(A) CH 3  C  Cl (B) C 6 H 5  C  NH 2 (C) CH 3  C  NH 2 (D) C 6 H 5  C  Cl
Q.17 Acetic anhydride is used as:
(A) Solvent (B) Dehydrating agent (C) Acetylating agent (D) Anticeptic

Q.18 In the given reaction:

O O
|| ||
[ X]
R  C  OH  R  C  O  CH 3
[X] will be:
(A) CH2N2 (B) CH3OH/H (C) MeCOOH (D) Me2SO4

Q.19 Which of the following gives silver mirror test?

(A) HCOOH (B) CH3COCHOHCH3
(C) Tartaric acid (D) Glucose

Q.20 An example of a primary amine is:

(A) n-Propylamine (B) Isopropylamine (C) t-Butyl amine (D) Sec. butyl amine

Q.21 Which compound is soluble in water:

(A) [(CH3)2NH2]+ Cl– (B) [CH3NH3]+Cl–
(C) [(CH3)3NH]+ Cl– (D) PhNO2

Q.22 Which compound will liberate CO2 from NaHCO3 solution:

(A) CH3CO NH2 (B) CH3NH2 (C) (CH3)4N+OH– (D) CH3N+H3Cl–

Q.23 Which of the following compound can be produced if 1-propane amine is treated with NaNO2 and HCl
(A) Propane-1-ol (B) Propane-2-ol (C) 2-Chloropropane (D) 2-Propaneamine

Q.24 Which of the following amine does not react with Hinsberg reagent to give base soluble product
(A) Neopentyl amine (B) secpropyl amine (C) diethyl amine (D) Ethyl methyl amine

Q.25 Ethylamine can be prepared by

(A) Curtius reaction (B) Hofmann reaction (C) Mendius reaction (D)Reduction of formaldoxime

Q.26 The presence of primary amines can be confirmed in laboratory by:

(A) Reaction with HNO2 (B) reaction with CHCl3 and alc. KOH
(C) Reaction with Grignard reagent (D) Reaction with acetyl chloride
Q.27 Select correct statement (s):
(A) Cyclohexanone is oxidised to caprolactone which is hydrolysed under the reaction conditions
(B) Baeyer-Villiger oxidation involves migration of H/alkyl/aryl groups which is in order H > tert-alkyl >
sec-alkyl > phenyl > primary alkyl > methyl
(C) Pinacolone (CH 3 )3 CCCH 3 is oxidised to t-butyl acetate by C6H5CO3H
||
O
(D) All of the above are correct statements
Q.28 Following equilibrium is favoured in the forward side because of:

3 H O + (CH3)3COH
 

(A) (CH3)3COr (alkoxide ) – a strong nucleophile is formed

(B) (CH 3)3C(carbocation) is formed

(C) formed is stabilised by resonance

(D) (a weak acid) is formed

Q.29 Column I Column II

(organic compounds oxidised by HIO4) (products of HIO4 oxidation)
(A) CH3 COCHO (P) PhCH = O + HCOOH
(B) 1,2-cyclohexane dione (Q) CH3CH2CHO + HOOCCH3
(C) PhCH (OH) CHO (R) HOOC (CH2)4COOH
(D) CH3CH2CH (OH) COCH3 (S) CH3COOH + HCOOH

Q.30 Column I Column II

(A) C 6 H 5  C  OC 2 H 5  H 3C  C  O  C 2 H 5  (P) Anhydrous ZnCl2
|| ||
O O

C 6 H 5  C  CH 2  C  OC 2H 5  C 2 H 5OH
|| ||
O O

(B) H 3C  C  OH + Cl2  ClCH 2  C  OH (Q) C2 H5 O r

|| ||
O O

(C) C6H6+(H3C–C=O)2O  C 6 H 5  C  CH 3 (R) Red P

||
O

(D)  CH3CH(OH)CH2CH2CH2OH (S) LiAlH4

Q.31 Column I Column II
(Reagents reacting with PhCH2COOH) (Product formed)
(A) CH3MgBr (P) PhCH2COCl
(B) PCl5 (Q) PhCH2COOCH3
(C) NH3, followed by heating (R) CH4
(D) CH3OH in the presence of conc. H2SO4 (S) PhCH2 CONH2
Q.32 Column I (Reactions) Column II (Products)

(A) 2CH3CH2NH2 + (P) N = CH

(B) (CH3)2NH + C6H5COCl (Q) (CH3)2N—

O
||
(C) + (R) (CH3)2N– C

O O
|| ||
(D) CH3CH2NH2 + SO2Cl (S) C 2 H 5 NH  C  CH 2CH 2  C  O 

Q.33 Column I Column II

NaNO  HCl
(A) R'NH2  2 
 (P) RR'N–N= O
NaNO  HCl
(B) PhNH2  2 
 (Q) Ph–N+  NCl–
NaNO  HCl
(C) PhN(CH3)2  2 
 (R) (CH3 )2N N=O

NaNO  HCl
(D) RR'NH2  2 
 (S) R'OH + N2
Q.34 Column I Column II
(A) PhCONH2  PhCH2OH (P) B2H6 AcOH H2O

(B)  CH2OH–(CH2)2–CHOH–C6H5 (Q) LiAlH4

(C) C6H5CH = CH– COOH C6H5 – CH = CH2OH (R) H2Pd BaSO4

(D) CH3COCl  CH3–CHO (S) None
Q.35 Column I Column II
(A) RCN reduction
  (P) 1° Amine
( i ) CH MgBr
(B) RCN  3  (Q) Alcohol
(ii ) H 2 O

(C) RNC hydrolysis

  (R) Ketone
(D) RNH2 HNO
2  (S) Acid
 EXERCISE - II

Complete the following equation by writting the missing A, B, C, D..................etc.

CH COOH  HOH
Q.1 HCCH 3  (A)  B + C  CH3COOH
excess

PCl
Q.2 Ester (A) 5  B + C aq
.KOH

 (CH3)2CHCH2OH

(D) LiAlH
 4  (CH3)2CHCH2OH

ND
Q.3 3  (A) Br
R–COOH  , KOH
2  (B) NaNO HCl
 2 (C)
 

Moist Ag O [O] D I  Na / C H OH H O
Q.4  B  C  (HCOO)2Ca  G  2 
A   2 5
 H 
 3
CH3CN   X
2 ,SOCl 2

J H
3O


Q.5 Acid (A) SOCl

2  C

PCl MeNH
Q.6 3  B  
  A 
O MeOH 2  C

Q.7 O= + A  O = + B  O = (uriede)

O=

CH ( COOC H )
Q.8 CaCN2 + HOH H2SO
4  (A) 2  
  (B)
2 5
( H 2O 2 )

 
Q.9  A  B


Q.10  A+B

Q.11 H
 (A)
 Zn / Hg / HCl
Q.12 PhMe + (A) AlCl
3  p–MeC6H4–CO–CH2–CH2COOH    (B)

(i ) Alk .KOH
Q.13 CH3(CH2)14CH2CH2COOH Br / PBr
2 3  (A)   

 (B) (
C)

( ii ) H

( i ) Ag  ( ii ) Br
CH3(CH2)14COOH    2  (D)

Q.14 LiAlH
4  (A) 
   (B)  HCl (C) BaO
 (D) + CO2+H2O


H / Pd
Q.15 +  2 
(A) (limited)
 (B)


  (i ) H O
OH OH 2
Q.16  (A)  (B)  
  (C)

(ii ) H 3O

H / Pd 
Q.17 HCCH (
i ) 2 Na
 (A) 2 
 (B) C  D
( ii ) 2 CO 2 BaSO 4


Q.18 Phthalic acid + NH3  D  E

Q.19 MeCH(CH2COOH)2 (

CH 3CO ) 2 O
  F


O H
|| |
LiAlH
Q.20 CH 3  C  N 4  (A)
 

LiAlH
Q.21 4  (B)
 

Give the mechanism for the reaction with suitable examples:

O
|| Br / 4 KOH 
Q.22 R  C  NH 2 + 2   R–NH2

O
||
Q.23 R  C  OR ' NaOH
 RCOONa + R'OH
 O O O
|| RONa
|| ||
Q.24   
R  C  OR ' MeCOOEt R  C  CH 2  C  OC 2 H 5

O
||
Q.25 R  C  OH  HN 3 H2SO
4  RNH2


O O
|| ||
AlCl 3
Q.26 R  C  Cl  R  C  C6 H 5

O
|| ( i ) Ag
Q.27 R  C  Cl + CH2N2  R–CH2–COOH
( ii ) H 2O

Account for following:

Q.28 Fluoro acetic acid is stronger than chloro acetic acid.

Q.29 C–O bond length in formic acid are 1.23 Å and 1.36 Å but in sodium formate both carbon and oxygen
bonds have same value i.e. 1.27 Å.

Q.30 Acetic acid can be halogenated in presence of phosphorous and chlorine but formic acid cannot be
halogenated in the same way.
Q.31 The C–G bond in acid derivative is expected to be shorter and stronger than alkyl derivative.

Q.32 An acyl chloride undergoes nucleophilic attack more rapidly than does an alkyl halide.

Q.33 Primary and secondary amide exist as dimer in solid and pure liquid state.
How will you bring about the following transformation:

Q.34 Propanoic acid into lactic acid.

Q.35 Nitroethane to acetic acid.

Q.36 Benzoic acid to benzamide.

Q.37 Ethyl benzene to 2-phenyl propionic acid.

Q.38 Acetamide from acetone.

Q.39 Tartartic acid from ethylene.

Q.40 Lactic acid from acetic acid.

Q.41 Pyruvic acid from ethyl bromide.

Q.42 -hydroxy propionic acid from ethylene oxide.

 EXERCISE - III

Q.1 Show by a series of equations how you could synthesize each of the following compounds from the
indicated starting material and any necessary organic or inorganic reagents.
(a) 2-Methylpropanoic acid from tert-butyl alcohol
(b) 3-Methylbutanoic acid from tert-butyl alcohol
(c) 3,3-Dimethylbutanoic acid from tert-butyl alcohol
(d) HO2C(CH2)5CO2H from HO2C(CH2)3CO2H
(e) 3-Phenyl-1-butanol from CH 3CHCH 2 CN
|
C6 H 5

(f) from cyclopentyl bromide

(g) from (E)–ClCH=CHCO2H

Q.2 On standing in dilute aqueous acid, compound A is smoothly converted to mevaionolactone.

(i ) H O 
3
  
( ii ) 

Suggest a reasonable mechanism for this reaction. What other organic product is also formed?

Q.3 Suggest reaction conditions suitable for the preparation of compound A from 5-hydroxy-2-hexynoic
acid.

CH 3CHCH 2C  CCO 2 H 
|
OH
5-Hydroxy-2-hexynoic acid Compound A

Q.4 Outline reasonable mechanism for each of the following reactions

+ BrMgCH2CH2CH2CH2MgBr (
i ) THF
(a) 

( ii ) H 2O

(b) 


Q.5 Identify compounds A through C in the following equations:

O O
|| ||
(a) CH3O CCl + CCH pyridine
  compound A (C22H18O4)
|
OH
 O O
|| || CH MgI (1. equiv ) diethyl ether
(b) CH 3CCH 2CH 2COCH 2CH 3 3        compound B (a lactone, C6H10O2)

(c) heat
 compound C (C9H4O5) + H2O

Q.6 An organic compound C4H6O4 (A) when heated with acetic anhydride give another compound C4H4O3
(B) which in turn react with ammonia to give a third compound C4H5O2N (C). Both (B) and (C) may be
hydrolysed to A. With chlorine A give monochloro-compound (D) which reacts with caustic potash to
give either C4H4O5K2 (E) or C4H2O4K2 (F) depending upon the condition of reaction. Identify the
compound A to F.
Q.7 An organic compound A (C4H9NO) on treatment with bromine and alkali form another compound B
(C3H9N) on treatment with sodium nitrite and dilute hydrochloric acid. B yield C (C3H8O). C can be
oxidized to D (C3H6O). Which can also synthesised from methyl acetylene. Identify the compound A to D.
Q.8 With bromine and caustic potash the straight chain compound C4H9ON (A) give C3H9N (B), with
caustic soda C4H7O2Na (C) and with phosphorous pentoxide gives C4H7N (D). With hydrochloric
acid D give C4H8O2 (E) of which C is the sodium salt. B may be converted to an alcohol (F) and then to
a halide the grignard reagent from which react with carbon dioxide to give E. On oxidation F give.
Identify the compound A to H.
Q.9 Compound (A) with an empirical formula, C7H9N on diazotization give a product which undergoes
reaction with Cu2Cl2 & HCl to give a compound (B). B on oxidation give a compound (C). Compound
(A) on treatment with Br2/H2O form C7H6NBr3 (D). Give the structural formula of A, B, C & D.

Q.10 An organic compound A (C3H5N) on boiling with alkali give ammonia and sodium slat of an acid B
(C3H6O2) A on reduction give a compound C (C3H9N) which with nitrous acid give D (C3H8O). Give
the structural formula of A, B, C and D.
Q.11 An organic compound (A) C3H7ON on heating with POCl2 give a compound B which on hydrolysis
give a compound (C) C3H6O2 with the liberation of ammonia. Compound A on treatment with LiAlH4
form compound C3H9N (D). Compound D treating with HNO2 liberate N2 gas on refluxing with
chloroform and alcoholic KOH give compound E which have foul smell. Identify compound A,B, C, D
and E.
Q.12 An organic compound A (C8H8O) an treatment with NH2OH. HCl give B and C. Compound B and C
can be converted into D and E respectively by treatment of H2SO4. Compound B, C, D and E are all
isomer of molecular formula C8H9NO. When D is boiled with KOH, and oil F (C6H7N) separate out.
F react rapidly with CH3COCl to give back (D). On other hand. E on boiling with alkali followed by
acidification give a white solid G (C7H6O2). Identify A to G.
Q.13 An organic compound A, (C8H9NO) on heating with conc. H2SO4 give another isomer of (A) i.e. (B)
C8H9NO. Compound B on hydrolysis with dil HCl give an aliphatic acid C, C2H4O2 and (D) on
treatment with NaNO2 HCl at 0°C give a compound (E) which give a white ppt. of AgCl on addition of
AgNO3. Compound (E) react with alkaline -naphthol to produce orange dye what are to E.

Q.14 An organic compound A of the molecular formula C4H8O3 give effervescence with sodium bicarbonate
solution and can be acetylated. It can be separated into dextro and laevoisomers on heating it forms an
acid B with formula C4H6O2. Compound B give positive Bayer's test. Identify A and B.
Q.15 An aromatic compound A, C8H5NO2 can be condensed with an acid derivative (B) C7H11O4 Br in
presence of alkali to form compound (C), C15H15NO6. Compound (B) can be prepared by action of
sodium followed by bromine gas on diethyl malonate. Compound (C) condensed again with ethyl chloro
acetate in presence of sodium to give compound (D) C19H21NO8. D on heating with a base can be
converted into E and a salt of acid F (C8H6O4). Compound A can be obtained by heating F with
ammonia. E on boiling with mineral acid produce amino acid G (C4H7NO4). Identify A to C.
Q.16 An organic acid A (C3H4O3) is catalytically reduced in presence of ammonia to give (B) C3H7NO2. B
react with acetyl chloride hydrochloric acid and alcohol. It can also react with nitrous acid to give
another compound (C) C3H6O3 along with evolution of N2. What are (A), (B) and (C)?
Q.17 A dibasic acid (A), C4H6O6, on heating with KHSO4 give a monobasic acid (B), C3H4O3, with the
elimination of CO2 and H2O. Acid (B) on reduction give another monobasic acid (C), C3H6O3. Both
(B) and (C) on heating with I2 and NaOH solution give yellow precipitate of iodoform and sodium
oxalate. Acid (A) react with two moles of acetyl chloride, while (C) reacts with one mole of acetyl
chloride. Acid (A) reacts with four moles of HI to form succinic acid, while (C) react with two moles of
HI to give propionic acid. Identify A, B, C and give equation for reaction.

Q.18 An organic compound of the formula C3H6O (A) gave iodoform test but not Tollen's and Fehling tests.
Two molecules of (A) condenes in presence of dry HCl gas to yield (B) of formula C6H10O. Compound
(B) decolourised Br2/CCl4 and cold dilute neutral KMnO4, but no ppt. with ammonical AgNO3 or
CuCl solution. It gave iodoform test and potassium salt of a compound on heating with I2 and KOH. The
potassium salt on treatment with H2SO4 gave compound (C) of formula C5H8O2. Compound (C) on
heating with sodalime gave (D) of formula C4H8. Identify compound A to D & write the chemical
equation.

Q.19 An organic compound (A) of formula C3H6O from a monoxime with hydroxylamine and form iodoform
on heating with I2 and NaOH and sodium acetate. Compound A on reaction with NaCN and dil. H2SO4
gave product B. Which on hydrolysis produced (C). Compound (C) on heating gave (D), which on
decarboxylation gave (E) of formula C3H6. Compound (E) on ozonolysis gave one molecule of
acetaldehyde and one of methanal. What are A to E?
Q.20 Two moles of an ester (A) are condensed in the presence of sodium ethoxide to give a -keto ester (B)
and ethanol. On heating in an acidic solution (B) gives ethanol and -keto acid (C). On decarboxylation
(C) gives 3-pentanone. Identify (A), (B) and (C) with proper reasoning. Name the reaction involved in
the conversion of (A) to (B).
Q.21 An acidic compound (A), C4H8O3 loses its optical activity on strong heating yielding (B), C4H6O2
which reacts readily with KMnO4. (B) forms a derivatives (C) with SOCl2, which on reaction with
(CH3)2 NH gives (D). The compound (A) on oxidation with dilute chromic acid gives an unstable
compound (E) which decarboxylates readily to give (F), C3H6O. The compound (F) gives a hydrocarbon
(G) on treatment with amalgamated Zn and HCl. Give structures of (A) to (G) with proper reasoning.
Q.22 An organic compound (A), C5H8O3 on heating with soda-lime gives (B),which reacts with HCN to give
(C). The compound (C) reacts with thionylchloride to produce (D), which on reaction with KCN gives
compound (E). Alkaline hydrolysis of (E) gives a salt (F), which on heating with soda-lime
produces -butane. Careful oxidation of (A) with dichromate gives acetic and malonic acid. Give structures
of (A) to (F) with proper reasoning.
Q.23 An acid (A), C8H7O2 Br on bromination in the presence of FeBr gives two isomers, (B) and (C) of
formula C8H6O2Br2. Vigorous oxidation of (A), (B) and (C) gives acids (D), (E) and (F) respectively.
(D), C7H5O2Br is the strongest acid among all of its isomers, whereas (E) and (F) each has a molecular
formula of C7H4O2Br2. Give structures of (A) to (F) with justification.
 EXERCISE - IV (A)
O
||
Q.1 The reaction of R  C  NH 2 with a mixture of Br2 and KOH gives R–NH2 as a product. The
intermediates involved in this reaction are: [IIT 1992]
O O
|| ||
(A) R  C  NHBr (B) R–N=C=O (C) R–NHBr (D) R  C  N

Q.2 Which of the following carboxylic acids undergo decarboxylation easily: [IIT 1995]
(A) C6H5CO–CH2COOH (B) C6H5COCOOH
(C) C 6 H 5CH 2  COOH (D) C 6 H 5CH 2  COOH
| |
OH NH 2

Q.3 The molecular weight of benzoic acid in benzene as determined by depression in freezing point method
corresponds to : [IIT 1996]
(A) Ionization of benzoic acid (B) Dimerisation of benzoic acid
(C) Trimerisation of benzoic acid (D) Solvation of benzoic acid

Q.4 When propionic acid is treated with aqueous NaHCO3, CO2 is liberated. The 'C' of CO2 comes from
(A) Methyl group (B) Carboxylic acid group
(C) methylene group (D) bicarbonate [IIT 1999]

Q.5 Benzoyl chloride is prepared from benzoic acid by: [IIT 2000]
(A) Cl2, hv (B) SO2Cl2 (C) SOCl2 (D) Cl2, H2O

Q.6 Which of the following acids has the smallest dissociation constant? [IIT 2002]
(A) CH3CHFCOOH (B) FCH2CH2COOH (C) BrCH2CH2COOH (D) CH3CHBrCOOH

Acidic

Q.7 Hydrolysis Products formed by P & Q can be differentiated by [IIT 2003]

(A) 2 & 4 DNP (B) Lucas reagent (ZnCl2)conc. HCl

(C) NaHSO3 (D) Fehlings solution

Q.8 When benzamid is treated with POCl3, the product is: [IIT 2004]
(A) Benzonitrile (B) Aniline (C) Chlorobenzene (D) Benzylamine

Q.9 Which of the following is obtained when 4-Methylbenzenesulphonic acid is hydrolysed with excess of
sodium acetate? [IIT 2005]
—
(A) CH3 CO O N a (B) CH3 + SO3


(C) CH3 SO 3 N a + CH3COOH (D) CH3 SO2O. COCH3 + NaOH
Q.10 The correct IUPAC name of C6H5COCl is
(A) Benzoyl chloride (B) Benzene chloro ketone
(C) Benzene carbonyl chloride (D) Chloro phenyl ketone [IIT 2006]

Q.11 Which of the following reactants on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product? [IIT 2006]

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

EXERCISE - IV (B)
Q.1 Compound (A) (C6H12O2) on reduction with LiAlH4 yielded two compounds (B) and (C). The compound
(B) on oxidation gave (D) which on treatment with aqueous alkali and subsequent heating furnished (E).
The latter on catalytic hydrogenation gave (C). The compound (D) was oxidised further to give (F)
which was found to be monobasic acid (molecular mass = 60.0). Deduce the structure of (A), (B), (C),
(D) and (E). [IIT 1990]
Q.2 In the following reactions, identify the compounds (A), (B), (C) and (D) [IIT 1994]
PCl5 + SO2  (A) + (B)
(A) + CH3COOH  (C) + SO2 + HCl
2(C) +b (CH3)2Cd  2(D) + CdCl2
Q.3 Complete the following equations by writing the missing A and B [IIT 1995]
(i) CH3CH2COOH P
/ Br2
 (A) (
i ) Alc.KOH ( excess)
    (B)
( ii ) H 

O
||
(ii) C4H8O3(A) CrO Warm
3  (B)  CH 3  C  CH 3  CO 2
Q.4 A mixture of an acid anhydride (A) and a monobasic acid (B) on heating produces another monobasic
acid (C) of equivalent weight 74 and an anhydride (D). The acids and anhydrides remain in equilibrium.
The anhydride (D) contains two identical fluoro-alkyl groups. The acid (B) contains a trifluoromethyl
group and has an equivalent weight of 128. Give structures of (A) to (D) with proper reasoning. (Atomic
weight of fluorine = 19). [IIT 1998]
Q.5 Identify A and B in the following equations: [IIT 1999]

O
||

( i ) OH H C  CH  C  OH
CH2 NaOEt
  (A) (B)    3
( ii ) H   |
CH 2  C  OH
||
O
Q.6 Write the structure of product A & B: [IIT 2000]
O
|| H3O 
CH 3  C  O18C2 H 5   A + B

Q.7 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
BaC*O3 + H2SO4 C (gas) [C* denotes C14] [IIT 2001]
( i ) Mg / ether LiAlH
CH 2  CH  Br    Y   4  Z
( ii ) X
( iii ) H3O 

Q.8 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? [IIT 2003]
Q.9 Give major products A, B, C and D in following reaction sequence. [IIT 2004]

KCN
 A (
i ) NaOEt / EtOH
   B 
H 3O
 C
DMF ( ii ) PhCHO / 
D
 ANSWER KEY
EXERCISE -I(A)

Q.1 C Q.2 B Q.3 C Q.4 B Q.5 C Q.6 A Q.7 A

Q.8 D Q.9 C Q.10 C Q.11 C Q.12 B Q.13 C Q.14 C
Q.15 A Q.16 D Q.17 B Q.18 C Q.19 A Q.20 A Q.21 A
Q.22 B Q.23 B Q.24 A Q.25 A Q.26 A Q.27 A Q.28 B
Q.29 D Q.30 C Q.31 A Q.32 C Q.33 A Q.34 B Q.35 D
Q.36 B Q.37 B Q.38 A Q.39 A Q.40 B Q.41 B Q.42 C
Q.43 A Q.44 A Q.45 A Q.46 D Q.47 C Q.48 B Q.49 C
Q.50 C Q.51 B Q.52 B Q.53 D Q.54 C Q.55 A Q.56 C
Q.57 A Q.58 D Q.59 C Q.60 C Q.61 D Q.62 C Q.63 A
Q.64 A Q.65 B Q.66 B Q.67 B Q.68 C Q.69 D Q.70 C
Q.71 D Q.72 C Q.73 A Q.74 C Q.75 A Q.76 C Q.77 A
Q.78 C Q.79 C Q.80 C

EXERCISE - I(B)
Q.1 A,B,C Q.2 B,C Q.3 A,B,C,D Q.4 A,B
Q.5 A,B,C Q.6 A,C Q.7 A,C,D Q.8 A,B,C,D
Q.9 A,B,C,D Q.10 A,B,C Q.11 A,B Q.12 A,B
Q.13 B,C Q.14 B,C Q.15 A,B,C,D Q.16 B
Q.17 A,B,C Q.18 A,B,D Q.19 A,B,C,D Q.20 A,B,C,D
Q.21 A,B,C Q.22 D Q.23 A,B,C Q.24 A,B
Q.25 A,B,C Q.26 B Q.27 D Q.28 B
Q.29 (A) S, (B) R, (C) P, (D) Q
Q.30 (A) Q, (B) R, (C) P, (D) S Q.31 (A) R, (B) P, (C) S, (D) Q
Q.32 (A) Q, (B) S, (C) P, (D) Q Q.33 (A) S, (B) Q, (C) P, (D) R
Q.34 (A) S, (B) Q, (C) S, (D) R Q.35 (A) P, (B) R, (C) P,S, (D) Q

EXERCISE - II
Q.1 (A) CH3CH(OOCCH3)2; (B) CH3CHO; (C) (CH3CO)2O
Q.2 (A) (CH3)2CHCOOCH2CH(CH3)2 ; (B) (CH3)2CHCOCl; (C) (CH3)2CHCH2Cl
Q.3 (A) RCOND2; (B) RNH2; (C) ROH
Q.4 (A) CH3Cl; (B) CH3OH; (C) HCOOH; (D) Ca(OH)2; (G) HCHO; (H) CH3Cl; (I) KCN; (J) CH3CN;
(X) CH3COOH
Q.5 (A) CH3COOH; (B) CH3COONa; (C) CH3COCl; (E) (CH3CO)2O
Q.6 (A) HOOCCH2CH2COOMe; (B) ClOCCH2CH2COOMe; (C) MeNHOCCH2CH2COOMe
Q.7 (A) 2NH3; (B) CH3COCl; (C) H2SO4 + SO3

Q.8 (A) H2NCONH2; (B) O = Q.9 (A) ; (B)

Q.10(A) (B) Q.11 (A)

Q.12 (A) ; (B) p-MeC6H4CH2CH2CH2COOH

Q.13 (A) CH3(CH2)14CH2CHBrCOOH; (B) CH3(CH2)14CH=CHCOOH; (C) KMnO4;

(D) CH3(CH2)14Br

Q.14 (A) ; (B) ; (C) CN–/H3O+ ; (D)

Q.15(A) ; (B) Q.16 (A) ; (B) ; (C)

Q.17 (A) C COOH ; (B) H  C  COOH ; (C) ; (D)

|| | ||
C COOH H  C  COOH

Q.18 (D) ; (E) Q.19 (F)

Q.20 (A) CH3CH2NH– Q.21

EXERCISE - III
CH 2COOH CH ClCOOH
Q.6 (A) | (B) (C) (D) | 2
CH 2COOH CH 2COOH
Succinic acid
CH 2 (OH )COOK CHCOOK
(E) | (F) | |
CH 2COOK CHCOOK
Potassium maleate
Q.7 (A) (CH3)2CHCONH2; (B) (CH3)2CHNH2 ; (C) (CH3)2CHOH ; (D) CH3COCH3
Q.8 (A) CH3CH2CH3CONH2; (B) CH3CH2CH2NH2; (C) CH3CH2CH2COONa; (D) CH3CH2CH2CN
(E) CH3CH2CH2COOH; (F) CH3CH2CH2OH ; (G) CH3CH2CHO; (H) CH3CH2COOH

Q.9 (A) (B) (C) (D)

Q.10 (A) CH3CH2CN ; (B) CH3CH2COOH; (C) CH3CH2CH2NH2; (D) CH3CH2CH2OH

Q.11 (A) CH3CH2CONH2; (B) C2H5CN; (C) C2H5COOH; (D) CH3CH2CH2NH2;
 
(E) CH3CH2CH2 N  C
 O CH 3 CH 3 OH O
|| | | | ||
C  CH 3 C  N  OH ; (C) C  N ;(D) NH  C  CH 3
Q.12 (A) ; (B)

O O
|| ||
C  NH  CH 3 C  OH
(E) ; (F) NH2 ; (G)

CH 3 O
| ||
Q.13 (A) C  N  OH ; (B) NH  C  CH 3 ; (C) CH COOH; (D) NH2
3

N 2 Cl 
(E)

OH
|
Q.14 (A) CH 3  CH  CH 2  COOH ; (B) CH3–CH=CH–COOH

Q.15 (A) ; (B) Br–CH(COOEt)2; (C) ;

COOEt
| COOEt
|
(D) CCH 2COOEt ; (E) H 2 N  CCH 2COOEt ; (F)
| |
COOEt COOEt
Q.16 (A) CH2 = C(OH)–COOH; (B) CH3–C(NH2)–COOH; (C) CH3CH(OH)–COOH

CH (OH)COOH
Q.17 (A) | ; (B) CH3–CO–COOH; (C) CH3–CH(OH)–COOH
CH (OH)COOH
Q.18 (A) CH3–CO–CH3; (B) (CH3)2C=CHCOCH3; (C) (CH3)2C=CHCOOH; (D) (CH3)2C=CH2
Q.19 (A)CH3–CO–CH3; (B) (CH3)2C(OH)CN; (C) (CH3)2C(OH)COOH; (D) CH2= C–(CH3)–COOH
(E) CH3–CH=CH2
Q.20 Claisen condensation, (A) C2H5COOC2H5; (B) C2H5COCH(CH3)COOC2H5;
(C) C2H5COCH(H3)COOH
Q.21 (A) CH3CH(OH)CH2COOH; (B) CH3CH=CHCOOH; (C) CH3CH=CHCOCl
(D) CH3–CH=CHCON(CH3)2; (E) CH3COCH2COOH; (F) CH3COCH3; (G) CH3CH2CH3
Q.22 (A) CH3–CO–CH2CH2–COOH; (B) CH3COCH2CH3; (C) CH3C(OH)(CN)CH2CH3
(D) CH3C(Cl)(CN)CH2CH3; (E) CH3C(CN)2CH2CH3; (F) CH3C(COONa)2CH2CH3

Q.23 (A) ; (B) ; (C) ; (D) ;

(E) ; (F)
 EXERCISE - IV (A)
Q.1 A,B Q.2 A Q.3 B Q.4 D Q.5 C Q.6 C Q.7 D
Q.8 A Q.9 C
EXERCISE - IV (B)

Q.1 (A) CH3CH2CH2COOCH2CH3; (B) CH3CH2OH ; (C) CH3CH2CH2CH2OH; (D) CH3CHO;

(E) CH3CH= CHCHO
Q.2 (A) SOCl2; (B) POCl3; (C) CH3COCl; (D) CH3COCH3
Q.3 (i) (A) CH3CHBrCOOH; (B) CH2 = CHCOOH;
(ii) (A) CH3CH(OH)CH2COOH; (B) CH3COCH2COOH
Q.4 (A) (CH3CH3CO)2O; (B) CF3CH2COOH; (C) CH3CH2COOH; (D) (CF3CH2CO)2O
HC  (COOC2 H5 ) 2
|
Q.5 (A) NaCH(COC2H5)2; (B) CH 3  HC  COOC2 H5
Q.6 (A) CH3COOH; (B) C2H5O18H
Q.7 BaC*O3 + H2SO4  C*O2(X) + BaSO4
(i ) Mg ,(ii ) C*O
CH2=CH–Br   2 
(iii ) H3O 

CH2=CH–C*OOH(Y) LiAlH
 4 

CH2=CHC*H2OH(Z) H
CH2=H–C* H 2 C* H 2 CH=C*H2
 Br–  Br–
CH2=CH–C*H2 Br BrCH2 – CH=C*H2
O3ZnH2O  O3ZnH2O Br–C*H2CHO + HCHO Br–CH2CHO + HC*HO
H
|
Ph H (  ) CH3CH 2 C OH
| | |
CH3
Q.8 CH 3  C  COOH + CH 3  C  COOH     
| | conc.H 2SO 4 , 
H Ph
(racemic mixture)
Ph H H H
| | | |
CH 3  C  C  O  C  CH 2CH 3 + CH 3  C  C  O  C  CH 2CH 3
| || | | || |
H O CH 3 Ph O CH 3
during esterification reaction only –COOH and –OH partcipates. There is no effect on structure or
configuration of carbon adjacent to these groups. So when(±) acid reacts with pure (+) alcohol two
esters are produced which are diastereoisomers of each other.

Q.9 (A) (B) (C) (D)