CARBOXYLIC ACID DERIVATIVES

Single answer type questions:

1. The correct explanation for the below reaction is
O O
- -
R - C - Cl + Nu R - C - Nu + Cl

A) O O O
- δ- δ-
R - C - Nu + Cl
-
Nu C - Cl Nu C Cl
R R

B) O O
O-
-
Nu- C - Cl Nu C Cl R - C - Nu + Cl

R R

C) O O O
-
Nu- C - Cl Nu C Cl R - C - Nu + Cl

R R

D) O
O O
- Cl- Nu-
R - C - Cl R - C⊕ R - C - Nu
2. O
3 CH MgBr ( excess )
O   HO → X,X
+ 
3
is
A) H 3C OH B) HO
OH OH
H 3C H 3C

C) O OH D) O

CH 3

3. Among the following, the acid which undergoes fastest decarboxylation is.
a) Ph CO COOH b) Ph CO CH 2COOH c) Ph COOH d) Ph CHOH COOH
4.

a) b)

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 c) d)
5.
12 14 O
CH 3 − CH 2 − OTs ||
CH 3 − C − OH

Product (or) the possible products

O O
12 14 14 12
CH 2 − CH 2 − O − C − CH 3 CH 2 − CH 2 − O − C − CH 3

a) b)

c) Both A and B d) None of these

6. Treatment of 4-methylphenyl acetate with AlCl3 produces

a) 3-chloro-4-methoxyphenyl acetate
b) 2-hydroxy-5-methylacetophenone
c) 4-acetyl-2-hydroxy-5-methylacetophenone
d) 3-hydroxy-6-methylacetophenone
7.

Br2/CCl4(1 eq) O
Mg/ether H+ / ∆
Ph O R 
→S
P Q
H 3O +
Product ‘S’ is

(A) (B)
O O

(C) (D)

8. The rate of dehydration (acid catalysed) and decarboxylation (base catalysed)

are respectively faster in …

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 O OH
O OH
COOH
O

COOH O
(I) (IV)
(II) (III)
(A) III and I (B) III and II
(C) IV and II (D) IV and I

CH3 O
–
(i) t − BuO
9. 
(ii) H O +
→ D. D is
3

N R
CH3 O
(a) (b)
N R N R
t-BuO
R R

(c) (d)
N N
10.

A) o – bromo benzoic acid (B) Phenyl acetic acid

C) p – bromo benzoic acid (D) m – bromo benzoic acid
11. The end product of the following reaction would be
OCH3
(i) H3O+
OCH3 (ii)
COCH3
O
OCH3
(A) O (B)
OCH3
COH COH
O O

(D) O

COCH3
(C) O
O

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12.
O
(B) C NH
(A) NH C H O

(C) NH CH3 (D)

HO NH2
O

CH 3
|
Ag O / H O
13. CH 3 − C − COOH 
SOCl
→ A  → B 
2
→ C . The compound ‘C is 2 2

|
CH N 2 2

CH 3

CH 3 CH 3
| |
(A) CH 3 − C − COOCH 3 (B) CH 3 − C − CO − CH 3
| |
CH 3 CH 3

CH 3 CH 3
| |
(C) CH 3 − C − CH 2OH (D) CH 3 − C − CH 2COOH
| |
CH 3 CH 3

14. O
(i) O 2/Ag/ ∆
∆
H2C OH (A) (B)
18 +
(ii) H 2O/ H
The product (B) is
18 18
OH OH OH OH
18 18
A) HO B) HO
C) HO D) HO
CH3 CH3 CH3 CH3

15. N2Cl
O O
A B C
 →  →  →

The reagents/conditions A, B and C are respectively

A) Ba(OH)2, KCN and CHCl3/NaOH heat, H3O+
B) H2O (boil), CO2/KOH and Ac2O – AcONa, heat
C) Steam ; CHCl3/NaOH, heat, H3O+ and Ac2O – AcONa, heat
D) Cu2Cl2/HCl, NaOH/high P and CO2|NaOH, heat
16. Consider the following statements for hydrolysis reaction:

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 I) is more reactive than C6 H 5COOC2 H 5

II) is more reactive than

III) ) is more reactive than

The correct option is :

(A) I and II (B) I, II and III (C) II and III (D) I and III

Number of possible cross products in the given reaction:

17.
C H ONa
CH3COOC2 H5 + C6 H5 − CH 2 − COOC2 H 5 
2 5
C H OH
→
2 5

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

(D) All the above are correct statements
18. In the given reaction sequence:

(A) (B)

(C) (D)

19.

. Y has more number of carbons than Z. If ‘Y’ is

treated with CH2N2 another compound ‘E’ is obtained. Correct statement
regarding E is ____
(A) E can be reduced by NaBH4
(B) ‘E’ on reduction with Dibal-H gives a compound which gives Iodoform test

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 (C) One of its isomer on reduction with LiAlH4 gives a compound which can
give Iodoform test
(D) E cannot exhibit keto-enol tautomerism
20. The final product on acid hydrolysis and decarboxylation of

(A) (B)

(C) (D)

21.

(A) (B)

(C) (D)

22. Reaction of acetic acid with hydrazoic acid gives

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 A) B) C) D)

23.
Heating with gives
A) B) C) D)

24.
The reaction of adipic acid with will give
A) Adipic anhydride B) Cyclopentane
C) Cyclopentanone D) Cyclohexanone

25. Reaction of on reaction with gives

A) B)
C) D)

26.

A) B) C) D)

27. An organic compound A (C7H6Br2) gives a pale yellow ppt with

warm alc. AgNO3 solution. A on treatment with dil. KMnO4 gives
a compound B (C7H5O2Br). B on treatment with AgOH followed
by heating with Br2/CCl4 gives a compound of which only two
mono nitro isomers are possible. A upon treatment with LiAlH4

gives C (C7H7Br). The product X

would be
A) B) C) D)

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 O

O C
H3 O
H3 C HC CH CH3 A B
28. O
A and B are
(a) CH 3CH 2 OOH, CH3CH 2 OH (b) H3 C CH CH3 , H3 C CH2 OH
COOH
H2 C CH2 COOH H2 C CH2
(c) H3 C CH COOH, CH3CHO (d) ,
OH OH OH OH

29.

30. An enantiomerically pure carboxylic acid is treated with racemic mixture of A

primary amine with one chiral carbon. The amide formed will be
(A) meso compound (B) Optically active mixture
(C) optically pure (D) racemic mixture
31. Compound which contains a carboxylic acid group among the following is
(A) Salicylaldehyde (B) Cinnamic acid

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 (C) Picric acid (D) Carbolic acid
32. Which of the following option is correct ?
CH3

CH2=CH COOH CH3

(A) CH3 ¾¾ ¾¾
NaOH
CaOH
® CH3–CH=C–CH3

(B) HOOC O ¾ ¾®
D O
COOH
(1) NaOH
(C) COOH (2) electrolysis
CH3 CH3
CH2–Cl CH2–OEt
(D) ¾¾
EtOH
D
¾®

Etooc OH

NaOMe
33. Ph Ph MeOH Product (major)

O O HO OH O O

2+

Ph Ph Ph Ph Ph Ph Ph Ph
a) b) c) d)

COCl 1. NaN
3

Br 2. ∆ , H2O
34. Product formed is
O
CH
C NH CH2 - NH
a) NH2 b) c) d)
Mg 1) CO2
PhCl A B. The compound B is
Dry ether 2) H3O+
35. 1.

a) PhMgCl b) Ph-CHO c) Ph-COOH d) Ph-CH2OH

36. One of the intermediate stages in the following synthesis, involved

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 (1) SOCl2
Ph-COOH
(2) CH2N2
Ph-CH2-COOH
(3) Ag2O /
(4) H2O
a) Iso-cyanate formation b) ketene formation
c) Betaine formation d) open carbocation formation
1) Na/xylene
............major product
2) H3O +
37. Ethyl adipate
O

- - O
a) HOCH2 (CH2)4-CH2OH b) HOCH2 ((CH2)3-CH2OH c) OH d)
38. The compound that undergoes decarboxylation most readily under mild
heating conditions is
COOH
COOH

COOH

(A) O (B)
COOH O
COOH COOH

(C) (D)

C 6 H5

39 C2H5ONa
O Identify the correct statement about product

A) It is a ketoaldehyde B) It exhibits tautomerism

C) It is a sodium salt of carboxylic acid D) It is an ethyl ester

CH COOH
40. 0
200 C BH3,THF +
[P] H [R]
- [Q]
H2O 2,OH
:
P and R respectively

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 O
A) CH2 OH
and

O
B) C
COOH
and OH

CH3
C) COOH
O
and
O
CH2 COOH
D) CH3
and

OH

41. An amide C3H7NO is hydrolysed. One of the products gives silver mirror test.
Other product can react with one molecule of benzene sulphonyl chloride to
produce an alkali insoluble product. Probable structure of amide is
O CH3
O
(A) || (B) H C N
CH3 − C − NH − CH 3
CH3
O O
(C) || (D) ||
CH 3 − CH 2 − C − NH 2 H − C − NH − CH 2 − CH3
O

O C
H3 O
H3 C HC CH CH3 A B
42. O
A and B are
(a) CH 3CH 2 OOH, CH3CH 2 OH (b) H3 C CH CH3 , H3 C CH2 OH
COOH
H2 C CH2 COOH H2 C CH2
(c) H3 C CH COOH, CH3CHO (d) ,
OH OH OH OH
43. The correct explanation for the below reaction is
O O
-
R - C - Cl + Nu- R - C - Nu + Cl

A) O O O
- δ- δ-
R - C - Nu + Cl
-
Nu C - Cl Nu C Cl
R R

B) O O
O-
-
Nu- C - Cl Nu C Cl R - C - Nu + Cl

R R

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 C) O O O
-
Nu- C - Cl Nu C Cl R - C - Nu + Cl

R R

D) O
O O
- Cl- Nu-
R - C - Cl R - C⊕ R - C - Nu

44. Two methods are generally used for preparation of carboxylic acid from alkyl
halides
+
Method: I - Cyanide method ( RX 
KCN H 3O
→ A  → RCOOH )
+
Method: II - Grignard method RX →
Mg CO2
 H
→ → RCOOH )
Which method is suitable for preparation of
COOH Cl

HO from HO

A) Method I B) Method II C) Both I & II D) neither I nor II

45. C N

HO 3S dilute.H SO / ∆KOBr / ∆
2 4 → C H NSO 
 7 7 4 ( → )
Br2 / H 2O
Product  → end product . The end product is

A) B) C) D)

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CAD – KEY SHEET
Single Answers
1 B 2 A 3 B 4 D 5 C 6 B
7 B 8 D 9 B 10 B 11 C 12 B
13 D 14 C 15 C 16 A 17 C 18 B
19 C 20 A 21 B 22 D 23 D 24 C
25 D 26 A 27 C 28 C 29 B 30 B
31 B 32 A 33 D 34 B 35 C 36 B
37 C 38 D 39 B 40 C 41 B 42 C
43 B 44 A 45 B

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 CAD – SOLUTIONS
Single solutions
1. Conceptual
2. Conceptual
3. Ph CO is electron withdrawing group at α − Carbon

4.
5. Conceptual
6. Fries rearrangement

7.
Mg
Br
Br2/CCl4 Mg/ether
Ph Ph
1 eq Ph
MgBr
Br (P)
O
O

Ph
Ph
H+ / ∆ Ph O MgBr
O OH OH

8.
O O O
OH
C O H
H+/A
base
;
(more stable)
O
O
H 2O

9. (b)

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 CH3 O CH2 CH2
+ t BuO O
N R N R N C R
O
+
H

R
N N
OH
10. C6 H 5CH 2 Br ( A ) → C6 H 5CH 2 MgBr ( B ) 
→ CNBr

C6 H 5CH 2CN ( C ) → C6 H 5CH 2COOH ( D )

11. (C)
CLEAVAGE OF ETHER LINKAGES, ACYL-OXYGEN CLEAVAGE BY ACIDIC
HYDROLYSIS AND FURTHER DECARBOXYLATION LEADS TO
CYCLOHEXANONE.

12. (B)
13. ( CH 3 )3 C − COOH  SOCl
→ ( CH 3 )3 C − COCl 
2 CH N
→ 2 2

(A)
( CH 3 )3 C − COCHN 2  → ( CH 3 )3 C − CH 2COOH
(B) (C)
14.

15. N2 Cl OH OH
O O
CHO
steam (i)CHCl3 / NaOH / ∆ (CH3CO)2 O
 →  → →
CH 3COONa
(ii) H O+
3
∆
Perkin's reaction

16. Conceptual
17. Each ester molecule forms one cation which attach the ester molecule.
18. Conceptual
19.

Page No - 15 -
20.

21. Coneptual
22. Schmidts reaction with acids is a modification of curtius reaction
23.
When heated with phosphorous pentoxide, or better with or ,
amides are dehydrated to alkyl cyanides.
24. With adipic acid anhydride formation would produce a seven-member ring and
does not take place. Instead carbon dioxide is lost and cyclopentanone, a
ketone with a five-member ring is formed.
25. Acetoacetic ester does not give the iodoform test as it contains an active
methylene group,

and it is this group that is halogenated and not the Me of the acetyl group.
26.

, ,

Page No - 16 -
27.

28. (c)
O H OH
O C O C OH
H3 O
CH3 HC CH CH3 CH3 CH CH CH3
O O

O OH O
O
CH3 CH
CH3 C H
+ CH3 CH C OH C OH
OH O CH
CH3
29. Hydrolysis of easter and alkene does not changes its configuration.
30. It will be diasteromeric mixture as chiral centres are not involved in the
reaction.
31. Conceptual

Page No - 17 -
32. (A)
CH3 CH3
CH2=CH–C CH2–CH=C–CH3
CH3
CH3
CH2=CH–C–COOH CH3
NaOH
CH3 CaO CH3–CH=C–CH3
(B) The bridge COOH can’t be easily decarboxylated by heating
COOH
NaOH
Electrolysis
(C) COOH
CH3 CH3
CH2–Cl EtOH CH
 → CH3
(D) 2
O
O- O O O
-
O O-
EtOOC OH EtO-C O- EtO
+ +

-
33. Ph Ph Meo Ph Ph Ph Ph -Eto- Ph Ph Ph Ph
R Br R Br
C ∆ C O
R CON3 H2 O
34. R N = C= O R - C - R + HBr + HNCO
35.

36.

37.

Page No - 18 -
38. SOL: Carbonyl group at beta carbon increases the rate of decarboxylation
greatly by chelation.
39.

40.

41. Conceptual
42. (c)

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 O H OH
O C O C OH
H3 O
CH3 HC CH CH3 CH3 CH CH CH3
O O

O OH O
O
CH3 CH
CH3 C H
+ CH3 CH C OH C OH
OH O CH
CH3

43. Conceptual
44. Conceptual
45.

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