ORGANIC CHEMISTRY

CARBOXYLIC ACIDS AND

IT'S DERIVATIVE ,
ALIPHATIC AMINES

Problem is just Distance between Expectation & Reality, so either expect less & Accept reality or
Expect a lot & turn it into reality. Your choice.
 EXERCISE -I
Q.1 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.2 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.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 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.6 Benzoic acid on treatment with hydrazoic acid (N3H) in the presence of concentrated sulphuric acid
gives:
(A) Benzamide (B) Sodium benzoate (C) Aniline (D) C6H5CON3

Carboxylic Acids & It's Derivative Aliphatic amines Page # 2

Q.7 In the given reaction :
O
|| ( i ) Br2 / KOH CHBr3 + [X]
C 6 H 5  C  CH 3   
(ii ) H 
[X] will be:
(A) C6H5–CHO (B) C6H5COOH (C) C6H5–CH2OH (D) CH3COOH

Q.8 In the given reaction:

O O
|| ||
C  CH 3  CH 3  C  OC 2 H 5 C
2 H5ONa
  [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.9 Number of cross products in the given reaction: (Without considering stereoisomers )
C 2 H5ONa
CH3COOC2H5 + C6H5–CH2–COOC2H5   
C 2 H 5OH
(A) One (B) Three (C) Two (D) four

Q.10 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

Carboxylic Acids & It's Derivative Aliphatic amines Page # 3

Q.11 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.12 In the given reaction :

PCl
3  [X]


[X] will be :

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

Q.13 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.14 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.15 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

Carboxylic Acids & It's Derivative Aliphatic amines Page # 4

Q.16 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.17 In the given reaction sequence:


( i ) KMnO 4 / O H /  ( i ) SOCl Br / KOH
 (A)  2  (B) 2  (C)
CH3–CH2–OH     
 ( ii ) NH 3 / 
(ii ) H
(C) will be :
(A) Methylamine (B) Eltylamine (C) Propylamine (D) Acetamide

Q.18 Sodium bicarbocate reacts with salicylic acid to form:

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

Q.19 Which one of the following on heating gives unsaturated acid:

(A) -Hydroxy acid (B) -Hydroxy acid (C) -Hyroxy acid (D) -Hydroxy acid

Q.20 Which will form lactone on treatment with NaOH ?

(A) -Bromo acid (B) -Bromo acid (C) -Hydroxy acid (D) -Bromo acid

Q.21 Which of the following will go decarboxylation on heating?

(A) Succinic acid (B) Phthalic acid (C) Malonic acid (D) Glutaric acid

Q.22 In the given reaction :

2 ( i ) Br / P
CH3–COOH    [X]
( ii ) NaCN
[X] will be: ( iii ) H 2O / H  / 
(A) CH3COOH (B) COOH–CH2–CH2–COOH
CH 2  CO
(C) | (D) CH2
CH 2  CO

Q.23 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
Carboxylic Acids & It's Derivative Aliphatic amines Page # 5
Q.24 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.25 Which one of the following reactions can be used for the preparation of -hydroxy ester:
(A) Perkin reaction (B) Reformatsky reaction
(C) Aldol condensation (D) Claisen condensation

Q.26 Which acid can be oxidised by Fehling solution:

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

Q.27 In the given reaction:

HBr
 [X]

[X] will be:

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

Q.28 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.29 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
Carboxylic Acids & It's Derivative Aliphatic amines Page # 6
Q.30 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.31 In the given reaction:

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

[X] will be :

(A) (B)

(C) (D)

Carboxylic Acids & It's Derivative Aliphatic amines Page # 7

Q.32 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.33 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.34 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.35 Which of the following compounds gives carbondioxide with NaHCO3?

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

Q.36 The reduction of benzoyl chloride with Pd and BaSO4/CaCO3 produces:

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

Q.37 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.38 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.39 N-Ethyl pthalimide on hydrolysis gives:

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

Carboxylic Acids & It's Derivative Aliphatic amines Page # 8

Q.40 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.41 Which of the following diazonium salt is relatively stable at 0-5°C:

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

Q.42 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.43 Which of the following can be detected by carbylamine reaction:

(A) Urea (B) CH3CONH2 (C) C2H5NH2 (D) All of above

Q.44 Hydrolysis of alkyl isocyanide yields:

(A) Primary amine (B) Tert. amine (C) Alcohol (D) Aldehyde

Q.45 Which of the following compound gives the smell of mustard oil:
(A) Alkyl isocyanate (B) Alkyl isothiocyanate
(C) Alkyl isocyanide (D) Alkyl isonitrile

Q.46 The compound obtained by the reaction between primary amine and aldehyde is:
(A) An amide (B) Imine (C) Nitrite (D) Nitro

Q.47 A reaction of ethyl amine & acetic anhydride leads to the formation of:
(A) CH3NHCOCH3 (B) C2H5CONHCH3
(C) CH3CONHC2H5 (D) CH3–CH=NOC2H5

Q.48 Identify X in the reaction

CHCl / KOH dil HCl

 3  Intermediate   X
heat 300 K

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

O
|| P2O5 CH MgBr
Q.49 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)

Carboxylic Acids & It's Derivative Aliphatic amines Page # 9

 ( i ) NH , 
3 ( i ) ND ,
Q.50 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.51 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.52 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.53 Acetic anhydride and ammonia gives the product:

(A) CH3CONH2 (B) CH3CONHCH3 (C) CH3CN (D) CH3COONH4

Q.54 Reductive amination of A forms:

A:

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

Q.55 An optically active compound 'X' has molecular formula C4H8O3. It evolves CO2 with aq. NaHCO3.
'X' reacts with LiAlH4 to give an achiral compound. 'X' is :
(A) CH 3CH 2CHCOOH (B) CH 3CHCOOH
| |
OH Me

(C) CH 3CHCOOH (D) CH 3CHCH 2 COOH

| |
CH 2OH OH

Carboxylic Acids & It's Derivative Aliphatic amines Page # 10

 EXERCISE - II

Q.1 Which of the following will liberate CO2 on reaction with NaHCO3

(A) OH (B) CH3COOH

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

Q.2 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.3 In the Hofmann bromamide degradation recation

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

Q.4 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.5 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.6 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.7 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

Carboxylic Acids & It's Derivative Aliphatic amines Page # 11

Q.8 Acetic acid can be used for the preparation of :
(A) Ethane (B) Methane (C) Acetone (D) ethanol

Q.9 Which of the following will form acetyl chloride with PCl5?
(A) MeCOOH (B) MeCOOMe
(C) MeCOOCOMe (D) Me–CONH2

Q.10 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.11 Which one of the following compounds will give HVZ reaction?

(A) (B)

(C) (D)

Q.12 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.13 Which one of the following acids undergoes decarboxylation on strong heating:
(A) Adipic acid (B) 3-butenoic acid (C) Formic acid (D) Salicylic acid

Q.14 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.15 Acetic anhydride is used as:

(A) Solvent (B) Dehydrating agent
(C) Acetylating agent (D) Anticeptic
Q.16 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

Carboxylic Acids & It's Derivative Aliphatic amines Page # 12

Q.17 Which of the following gives silver mirror test?
(A) HCOOH (B) CH3COCHOHCH3
(C) Tartaric acid (D) Glucose

Q.18 Which compound is soluble in water:

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

Q.19 Which compound will liberate CO2 from NaHCO3 solution:

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

Q.20 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.21 Which of the following amine reacts with Hinsberg reagent to give base soluble product
(A) Neopentyl amine (B) secpropyl amine (C) diethyl amine (D) Ethyl methyl amine

Q.22 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.23 Hofmann degradation is given by:

(A) Imide (B) Acid chloride (C) Acid anhydride (D) Amide

Q.24 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.25 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

Carboxylic Acids & It's Derivative Aliphatic amines Page # 13

Q.26 Column I (Reactions) Column II (Products)

(A) 2CH3NH2 + (P) N = CH

(B) (CH3)2NH + C6H5COCl (Q) CH3 – NH—

O
||
(C) + (R) (CH3)2N– C

O O
|| ||
(D) CH3NH2 + SO2Cl (S) CH 3 NH  C  CH 2CH 2  C  O 

Q.27 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'NH  2 
 (S) R'OH + N2

Q.28 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.29 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

Carboxylic Acids & It's Derivative Aliphatic amines Page # 14

 EXERCISE - III

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

PCl
Q.1 Ester (A) 5  B + C aq
.KOH
 (CH3)2CHCH2OH


(D) LiAlH
 4  (CH3)2CHCH2OH

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

Q.3 Acid (A) SOCl

2  C

PCl MeNH
Q.4 3  B  
  A 
O MeOH 2  C

 
Q.5  A  B


Q.6  A+B

Q.7 H
 (A)

Zn / Hg / HCl
Q.8 PhMe + (A) AlCl
3  p–MeC6H4–CO–CH2–CH2COOH    (B)

(i ) Alk .KOH
Q.9 CH3(CH2)14CH2CH2COOH Br / PBr
2 3  (A)   

 (B) (
C)

( ii ) H

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

Q.10 LiAlH
4  (A) 
   (B)  HCl (C) BaO
 (D) + CO2+H2O


H / Pd
Q.11 +  2 
(A) (limited)
 (B)


Carboxylic Acids & It's Derivative Aliphatic amines Page # 15

   (i ) H O
OH OH 2
Q.12  (A)  (B)  
  (C)

(ii ) H 3O

H / Pd 
Q.13 HCCH (
i ) 2 Na
 (A) 2 
 (B) C  D
( ii ) 2 CO 2 BaSO 4


Q.14 Phthalic acid + NH3  D  E

Q.15 MeCH(CH2COOH)2 (

CH 3CO ) 2 O
  F


O H
|| |
LiAlH
Q.16 CH 3  C  N 4  (A)
 

LiAlH
Q.17 4  (B)
 

Give the mechanism for the reaction with suitable examples:

O
|| Br / 4 KOH 
Q.18 R  C  NH 2 + 2   R–NH2

O
||
Q.19 R  C  OR ' NaOH
 RCOONa + R'OH
O O O
|| RONa
| | ||
Q.20   
R  C  OR ' MeCOOEt R  C  CH 2  C  OC 2 H 5

O
||
Q.21 R  C  OH  HN 3 H2SO
4  RNH2


O O
|| AlCl ||
Q.22 R  C  Cl 3  R  C  C 6 H 5
C6 H 6

O
|| ( i ) Ag
Q.23 R  C  Cl + CH2N2  R–CH2–COOH
( ii ) H 2O

Carboxylic Acids & It's Derivative Aliphatic amines Page # 16

 Account for following:

Q.24 Fluoro acetic acid is stronger than chloro acetic acid.

Q.25 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.26 Acetic acid can be halogenated in presence of phosphorous and chlorine but formic acid cannot be
halogenated in the same way.

Q.27 The C–G bond in acid derivative is expected to be shorter and stronger than alkyl derivative.

Q.28 An acyl chloride undergoes nucleophilic attack more rapidly than does an alkyl halide.

Q.29 Primary and secondary amide exist as dimer in solid and pure liquid state.
How will you bring about the following transformation:

Q.30 Propanoic acid into lactic acid.

Q.31 Nitroethane to acetic acid.

Q.32 Benzoic acid to benzamide.

Q.33 Ethyl benzene to 2-phenyl propionic acid.

Q.34 Acetamide from acetone.

Q.35 Tartartic acid from ethylene.

Q.36 Lactic acid from acetic acid.

Q.37 Pyruvic acid from ethyl bromide.

Q.38 -hydroxy propionic acid from ethylene oxide.

Carboxylic Acids & It's Derivative Aliphatic amines Page # 17

 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

Q.7 When benzamid is treated with POCl3, the product is: [IIT 2004]
(A) Benzonitrile (B) Aniline (C) Chlorobenzene (D) Benzylamine

Q.8 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.9 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)

Carboxylic Acids & It's Derivative Aliphatic amines Page # 18

Q.10 Match the compounds in Column I with their characteristic test(s)/reaction(s) given in Column II.
Indicate your answer by darkening the appropriate bubbles of the 4 × 4 matrix given in the ORS.
[IIT 2008]
Column I Column II
+ -
(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

Q.11 Match each of the compound in Column I with its characteristic reaction(s) in Column II.
Column I Column II [IIT 2009]
(A) CH3 CH2CH2CN (P) Reduction with Pd–C / H2
(B) CH3CH2 OCOCH3 (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) Reduction with diisobutylaluminium hydride
(DIBAL – H)
(T) Alkaline hydrolysis

Q.12 Match each of the compounds given in Column I with the reaction(s), that they can undergo, given in
Column II. [IIT 2009]
Column I Column II
Br
(A) (P) Nucleophilic substitution
O

(B) OH (Q) Elimination

CHO
(C) (R) Nucleophilic addition
OH
Br
(D) (S) Esterification with acetic anhydride
NO2
(T) Dehydrogenation

Carboxylic Acids & It's Derivative Aliphatic amines Page # 19

 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  O18C 2 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
followed by ozonolysis.
BaC*O3 + H2SO4  X (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]

Carboxylic Acids & It's Derivative Aliphatic amines Page # 20

 ANSWER KEY

EXERCISE -I
Q.1 D Q.2 C Q.3 C Q.4 B Q.5 A Q.6 C Q.7 B
Q.8 C Q.9 C Q.10 C Q.11 A Q.12 B Q.13 D Q.14 B
Q.15 A Q.16 A Q.17 A Q.18 B Q.19 B Q.20 D Q.21 C
Q.22 A Q.23 C Q.24 A Q.25 B Q.26 D Q.27 B Q.28 B
Q.29 A Q.30 A Q.31 B Q.32 B Q.33 C Q.34 A Q.35 A
Q.36 C Q.37 B Q.38 C Q.39 B Q.40 C Q.41 C Q.42 D
Q.43 C Q.44 A Q.45 B Q.46 B Q.47 C Q.48 D Q.49 C
Q.50 A Q.51 C Q.52 C Q.53 A Q.54 C Q.55 C

EXERCISE - II

Q.1 B,C Q.2 A,B,C,D Q.3 A,B Q.4 A,B,C

Q.5 A,C Q.6 A,C,D Q.7 A,B,C,D Q.8 A,B,C,D
Q.9 A,B,C Q.10 A,B Q.11 B,C Q.12 B,C
Q.13 A,B,C,D Q.14 B Q.15 A,B,C Q.16 A,B,D
Q.17 A,B,C,D Q.18 A,B,C Q.19 D Q.20 A,B,C
Q.21 A,B Q.22 B Q.23 A,D
Q.24 (A) S, (B) R, (C) P, (D) Q Q.25 (A) R, (B) P, (C) S, (D) Q
Q.26 (A) S, (B) R, (C) P, (D) Q Q.27 (A) S, (B) Q, (C) R, (D) P
Q.28 (A) S, (B) Q, (C) S, (D) R Q.29 (A) P, (B) R, (C) P,S, (D) Q

EXERCISE - III

Q.1 (A) (CH3)2CHCOOCH2CH(CH3)2 ; (B) (CH3)2CHCOCl; (C) (CH3)2CHCH2Cl

Q.2 (A) RCOND2; (B) RNH2; (C) ROH

Q.3 (A) R–COOH; (B) R–COONa; (C) R–COCl; (E) (R–CO)2O

Q.4 (A) HOOCCH2CH2COOMe; (B) ClOCCH2CH2COOMe; (C) MeNHOCCH2CH2COOMe

Q.5 (A) ; (B)

Q.6 (A) (B)

Q.7 (A)

Carboxylic Acids & It's Derivative Aliphatic amines Page # 21

Q.8 (A) ; (B) p-MeC6H4CH2CH2CH2COOH

Q.9 (A) CH3(CH2)14CH2CHBrCOOH; (B) CH3(CH2)14CH=CHCOOH; (C) KMnO4;

(D) CH3(CH2)14Br

Q.10 (A) ; (B) ; (C) CN–/H3O+ ; (D)

Q.11 (A) ; (B)

Q.12 (A) ; (B) ; (C)

Q.13 (A) C COOH ; (B) H  C  COOH ; (C) ; (D)

|| | ||
C COOH H  C  COOH

Q.14 (D) ; (E)

Q.15 (F)

Q.16 (A) CH3CH2NH–

Q.17

EXERCISE - IV (A)
Q.1 A,B Q.2 A Q.3 B Q.4 D Q.5 C Q.6 C Q.7 A
Q.8 C Q.9 C Q.10 (A) R,S ;(B) P,Q; (C) P,Q,R ;(D) P,S
Q.11 (A) P,Q,S,T (B) P,S,T (C) P (D) R Q.12 (A) P,Q,T (B) P,S,T (C) R,S (D) P
 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) CH3CH2COOCOCH2CF3 ; (B) CF3CH2COOH; (C) CH3CH2COOH; (D) (CF3CH2CO)2O

HC  (COOC2 H 5 ) 2
|
Q.5 (A) NaCH(COC2H5)2; (B) CH 3  HC  COOC2 H 5
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.

Carboxylic Acids & It's Derivative Aliphatic amines Page # 23