ORGANIC CHEMISTRY

DPP
DAILY PRACTICE PROBLEMS
TARGET
JEE/NEET/AIIMS

Addition and Condensation of Enols and Enolate ions DPP: - 7

Section-I 12. When acetic anhydride adds on an aromatic aldehyde in presence

Straight Objective Questions (Q.No. 1 to 108) of sodium acetate, the product formed is:
1. Which one of the following does not give Cannizzaro reaction? (a) P, y-unsaturated ester(b) a, |3-unsaturated aldehyde
(a) Formaldehyde (c) P-hydroxy acid(d) a, (3-unsaturated acid
(b) Benzaldehyde 13. Which one of the following will give a positive iodoform test?
(c) 2 ,2 -dimethyl propanaldehyde (a) CH3OH
(d) Acetaldehyde (b) CH 3— CH 2— CHOH— CH 2— CH 3
(c) CH 3— CHOH— CH 2— CH3'
2. Aldehydes and ketones react with a-bromo esters and zinc to yield:
(d) C6H 5 CH2OH
(a) a-keto esters (b) 3 -hydroxy esters
14. In the reaction
(c) y-keto acids (d) 8 -hydroxy esters
3. Which one of the following is formed when ethyl acetate is treated *0
with sodium ethoxide in ethanol?
Z & L [X]
(a) Ethyl 'acetoacetate (b) Sodio acetoacetic ester
'C l
(c) Ethyl butyrate (d) Malonic ester
product [X] is:
4. Which one of the following compounds will form an enolate ion
most readily?
(a) Ethyl acetoacetate (b) HCHO
(c) CH 3CHO (d) CH 3COCH 3
5. Which one of the compounds will not give yellow precipitate with
h/NaOH?
(a) Ethanol (b) Acetone (c) HOCH2— CH2— c h 2— COOC2H5
(c) Diethyl ketone (d) Acetophenone (d) Cl— CH2—CH2— CH2- C O O C 2H5
6 . Which of the following compounds will react with 15. Which one of the following will give haloform?
C 2 H 5OH/HOH/KCN: (a) CH3COCH2COOC2H5 (b) Cl— CH2— COCH2CH3
(a) Ethylamine (b) Benzoic acid
Ck
(c) Benzamide (d) Benzaldehyde (c) CH— CO— CH2— CH 3 (d) all of these
7. The product in the reaction, Cl >
( i)Z n 16. In the given reaction sequence,
C6H 5CHO + Br— CH 2— COOC 2 H 5
(ii) H (i) K C N /C1H5OH
is: C 6 H 5CHO- * [X]
(ii) H ,0 \H
(a) C 6H 5— CH2— COOH (ii) conc. HNO3
(b) C 6H5 — C H = C H — COOC 2H 5
[X] is:
(c) C 6H 5COOC 2 H5
(a) C6H5COOH (b) C 6H 5 COCOC 6H 5
(d) C 6H 5— CH2— CHO
(c) C6H5COCHOHC6H 5 . (d) C6H5CH2OH
8. Reaction not involving carbanion is:
17. Which one of the following acids is thermally most unstable?
(a) Aldol condensation (b) Claisen condensation (a) CH3— CO—COOH
(c) Dehydration of alcohol (d) Perkin reaction (b) CH3COCH2COOH
9. Which of the following cannot form carbanion when treated wtih (c) CH3— CO— CH2— CH2— COOH
dil NaOH? (d) CH3COCH2— CH2— CH2— COOH
(a) CH3— CH2—CHO (b) CH3— CH— CHO 18. The cannizzaro reaction of a benzaldehyde involves an:
(a) Intramolecular shift of proton
CH3 (b) Intermolecular shift of hydride
(c) Intermolecular shift of proton
CH3
(d) Intramolecular shift of hydride
(c) CH3— C— CHO (d) CH3— CH 2— CN 19. Which one of the following compounds will be obtained when
diethyl adipate is heated with sodium ethoxide in ethanol?
CH3
O
10. Acetophenone and Benzophenone can be distinguished by:
(a) Tollens test
(c) Iodoform test
(b) Moliesch test
(d) DNP test
11. Cinnamic acid can be prepared by which of the following reaction,
A cf
starting from benzaldehyde:
(a) Cannizzaro reaction (b) Perkin reaction (C)
(c) Claisen reaction (d) Rosenmund’s reaction
[Hint: The reaction is Stobbe condensation]
20. In the reaction [X] as major product is:
O O O
II CjH. ;ONa CH,
CH,— C— CH, + O
x j
Product
c 2h . OH
<»
the product is:
CHj n
OH OH

(b)CH j— C
o - f - a - o CH3 (d>
CH, CH

CH, 26. Number of aldol products in the given reaction

(c) CH, £ " X l C6H5— CHO + CH3— CHO

e
OH
—>
OH OHl is:
(a) One (b) Two
[Hint: The reaction is Knoevenagel reaction] (c) Three (d) Four
21. In the reaction 27. The number of aldol products between acetaldehyde and
O propanaldehyde will be:
(a) One (b) Two
■CH .“ CH— C— CH 3
(c) Three (d) Four
Base
28. CH 3CI can be converted into methylene cyclohexane by which one
o of the following pairs?
(a) Cyclohexanone, Wittig reaction

how is the product formed?

c a (b) Cyclopentanone, Wittig reaction
(c) Cyclopentane carboaldehyde, Wittig reaction
(a) Micheal addition followed by aldol condensation
(d) Cyclohexanone, Claisen condensation
(b) Aldol condensation followed by Micheal addition
29. The product of the given reaction
(c) Mannich reaction
(d) Knoevenagel reaction followed by aldol condensation
22. The suitable reagent(s) to bring about the given transformation CH,— CH— Cl [X]
(ii) B3ULI
uU Oi
OCH:
CHO CH,OH .CH;
CH, (iii)
CH

is: ^ 'CHO COONa

^O C H j ___ .O C H j
(a) KCN
(b) UAIH 4 followed by Tollens reagent (a) CH,-
,wch’T ^ X ™ .
(c) Tollens reagent followed by NaBH4 :H, CH,
(d) 50% NaOH
^^O C H j . ___ .O C H j
23. Thiophene reacts with HCHO in the presence of aqueous NaOH
to give: (c)CHj— CH-

CH,[, CH,
» 0 - c H2OH v Q - c OONa

30. In the given reaction

CH3 O
(c)0 - HjOH (d )^ - ^ _ ch3
s s I II (i) conc. NaOH
CH3— c --
24. In the given reaction
CH3 (ii) H
0 ? pofluct is:
.C H , H jC vJ L q
[XL
u CH3

(a) CH3—C— CHOH—CH 2 OH

ch3

(b) CH3— C— CH O H -CO O H

Reagent [X] is:
(a) NaH (b) NaNH2 CH3 CH3
(c) NaOH (d) LDA
CH3 O CH3 O
25. In the given reaction
I II I II
O (c) CH3— C---- C— COOH (d) CH3— C-- C— CH 2 OH

jA ^ CH3 CH3 CH3

(i) NaHYTHF
[X]
(ii) CHj—I 31. Which one of the following compounds exists in only enol form?
 o
H3C
(a) (b) (c) and CH,— CHO
O
0 and CHj— CH2—CHO
(d)
-CH,
(c) I I (d) All of these
36. In the given reaction (P) will be:

32. In the given reaction CH3\ f HO

^ C = C H — C— CH3 + CH3— NH2----------- » -> (P)
d o /o d CH/
CH3— CH 2— CH—CO— C6H5------ * (P)
O
ch3 CH3 CH3
(a) ^ C = C H — C = N — CH3 (b) CH— CH—C— CH3
(P) will be:
CH3 CH3 I
' D D CH3 NH— CH3

(a) CH3— CH2— C— COC6H5 (b) CH3— C— CH—COC6H5 O NH— CH3

ch3 ch3
CH3 D ch3
(c) C— CH2— C— CH3 (d) V C==rCHH-—i CH—C H 3
CH3 CH3/
D NH— CH3

(c) CH3—CHD— CD—COC6H5 (d) CH3— C— CD— COC6H5 37. In the given reaction

CH3 C ch 3 O
33. Aldol addition is given by:
|| PHCH&CuLi (p )
(a) CH3— CHO (b) CH3— CH— CHO
(ii) H jO
CH3

(c) CH3—CH2— CHO (d) All of these

34. In the given reaction product (P) will be: (P) will be:

O O
OH/A
CH3— C-CH 2— CH2— C— CH3------- > (P)

o o
(c)HjC — CHj (d)
(a) | |^0H (b) [___11
SCH3 'C H ,

O O 38. The given reaction

OH A ii
(c) c — CH, (d) A —
CH, H,C
CH—C6H5
C6H5— CHO +
35. In the given reaction:
is an example of:
O OH (a) Aldol addition
(b) Aldol condensation
A +B
dil base C» 3 (c) Claisen Schmidt reaction
(d) Claisen condensation
(A) and (B) will be: 39. The given reaction
0 ©
OH/4
CHj—C— (CH2)4 C CH3
H (X JL ^ CH0
(a) Y Y and CHj—CHO C— CH,
O O CH,
0 II
0
is known as:
(b) [ ] and CH3- C H 2—CHO
(a) Aldol addition
(b) Intramolecular aldol condensation
 (c) intermolecular aldol condensation O
(d) intramolecular Claisen condensation II
40. In the given reaction (a) CH 3— CH 2 — C— CH 2— COOCH 3

O O
II
(b) CH 3— C— CH— COOCH 3
D,0
(P)
NaOD ch3
(P) will be O
O II
(c) CH 3— CH 2— C— CH— COOC 2 H 5 and

CH 3 .

O
' II
CH 3— C— CH 2— COOC 2 H 5
(d) Mixture of all these products
45. Which of the following reactions will give (3-keto aldehyde as the
final product?
41. The given reaction

CH3— CHO + CH 3— CHO-

OH
I
• CH 3— CH—C H 2— CHO
w
O O + HCOOC 2 H 5
(excess) ©
©
(i) C 2H5Q

is catalysed by: (‘°H ©

(a) Acid only (b) base only (b )/ \ = o + c h , c o o c 2h , (|)C?H? ° ,
(c) both acid and base (d) H 2O
\ ___ / (excess)
(i>) H
*

O
,0
42. Which of the following esters will give successful Claisen
©
condensation reaction with HCOOC 2 H 5 in the presence of (i) C 2H >
C 2 H 5ONa/C 2 H5 OH? (c )^ ^ = 0 + c 2 h 5o — c — o c 2h 5
©
(H) H
(a) C 6 H 5— C H - C O O C 2 H 5 (b) C 6H 5 — CO OC 2 H 5
(d) All of these
CH 3
46. Which of the following dicarbonyl compounds will form five
(c) C 6H 5— CH 2— COOC 2 H5 (d) All of these membered ring product by intramolecular aldol reaction?
43. In the given reaction (a) 1,6-diketone (b) 1,5-diketone
(c) 1,7 diketone (d) All of these
CH 3— CH 2— COOC 2H 5 + HCOOC 2 H 5 -C
^ )
47. Which one of the following compounds on intramolecular aldol
addition, will give cyclohexanone derivative?
the major product will be:
(a) 1,6-diketone (b) 1,5-diketone
O
II (c) 1,7-diketone (d) all of these
(a) CH 3— CH 2— C— CH— CO OC 2H 3 48. Which of the following acids would undergo decarboxylation on
heating?
CH 3
O
O II
(a) CH 3— CH 2— CH 2— C— C H 2— COOH
(b) CH 3— CH 2— C— C— COOC 2H 5 (c) COOH— CH— COOH
CH 3 CH 3
O O
II
(c) H— C— CH— COOC 2H 5
OOH
(b)
CH 3

O (d) All of these

II e 49. Which of the following compounds will give Perkin reaction with
(d) H— C— C— COOC 2 H 5 benzaldehyde in the presence of base?
(a) (CH 3— C H 2C 0 )20 (b) (CH 3— CH— C 0 )20
CH3
44. In the given reaction CH 3
O O O CH 3
II II (i) C H 3O
CH 3— C H j- C — o c h 3 + c h 3— c — o c h 3
('i) H * ’ (c) (C 6H 5 C 0 ) 2 0 (d) C 6H 5—C — O - C — C— CH 3
the product is: CH 3
50. Which one of the following compounds would be most reactive O O
for Perkin condensation reaction with acetic anhydride? II II
(a) CH2= C H — C— CH 3 (b) CH 2= C — C— CH 2— CHj

(a) (b)CH 3Q—

ch3

0
(c) H3C~^\0 ) — CHQ ( d ) C I - ^ Q ^ —CHO II
(c) CH 3— C H = C — CHO (d) CH 2= C — C— C 6H 5

51. The given reaction is known as CH 3 CH 3

CH jC O O N a [Hint: Formaldehyde does not give aldol condensation reaction ]
C 6H5CHO + (CH3 C 0 )20
C 6H 5— C H = C H — COOH + CH 3COOH
"5"
59. Which halo derivatives on treatment with OH will give carboxylic
(a) Benzoin condensation (b) Perkin reaction acid?
(c) Reformatsky reaction (d) Knoevenagel condensation O 0
52. Cinnamic acid from benzaldehyde would be prepared by which of II
the following reactions? (a) CH 3— CH— C— CH 2— CH 3
(b)
(a) Perkin reaction (b) Reformatsky reaction Br
(c) Knoevenagel condensation (d) All of these
53. Which one of the following compounds would not give
O
Knoevenagel condensation with benzaldehyde? (c) CH3— C— CCI 3 (d) All of these
0
COOC 2H 5 COCH 3 60. Which halo derivatives on treatment with X 2 /OH will give
(a) c h 2: (b) CH 2 carboxylic acid with the loss of one carbon atom?
COOC 2H 5 CO OC 2H 5
O O
(a) CH 3— C— CH 2CI (b) CH 3— C— CH 2— CH2Br
(d) C 2 H 5— O— C— O C 2 H5
(c)
o Cl O
O
Cl
54. In which reaction zinc enolate behaves as a nucleophile?
(a) Aldol addition (b) Claisen condensation (c) CH 3— CH— C— CH 2— CH 3 (d) |
(c) Reformatsky reaction (d) All of these
61. Which one of the following compounds will give Cannizzaro
55. Stobbe condensation would take place between acetone and which
reaction?
of thee following compounds in the presence of strong base?

O O
(a) C6H5— C— CHO (b) CH3— C— CHO
(a) C 2 H 5O— C— OC 2 H5 (b) HCOOC 2H 5
COOC 2 H5 CH 2— COOC 2 H 5 O
(c) I (d) I
(c) CH 3— CH 2— C— H (d) CH 3— CHO
COOC 2 H5 CH 2— COOC 2 H 5
62. Which of the following compounds gives intramolecular
56. The given conversion can be performed by which of the following
Canizzaro reaction?
reactions?

O CHO
O
H2— CH j— C— CHj (b) o
CHO

(a) Michael addition (b) Enamine synthesis

(c) both (a) and (b) (d) Mannich reaction (d) AH o f these
57. In the given reaction

CHO

CHO 63. In the given reaction

(i) C2HjONa\C2H5OH

(ii) R CH3— C H 2— COOH * '" * > ^ (A)

(R) would be: (A) would be:

(a) HCHO (b) CH 3CHO
O
(c) HCOOC 2 H5 (d) (COOC2H5h
(a) CH3—CH 2— C— Br (b) CH3— CH OH
58. Which of the following compounds can be prepared using aldol
condensation? NH2
 o o

(c) CH3—CH— COOH (d) CH3— CH— C— NH2 C6H5— C—OC2H5.

rv •
Br nh2 Select the correct answer from the codes given below:
Codes:
64. In the given reaction
(a) II > I > III > IV (b) I > II > III > IV
O
II P B r, C H jO H
(c) III > II > I > IV (d) IV > III > I > II
CH3— CH2— C—OH -»------ > (B) 72. In Benzoin condensation which of the following are formed as
B r2
intermediate compounds?
(B) will be:
O O
0
(a) CH3— CH2— C— OCH3 (b) CH3— CH— COOH (a) Ar— C— CN (b) Ar— C = C = N

OCH3 H OH

(c) CH3— CH— COOCH3 (d) CH3— CH— COOCH3 0

0 OH
Br OCH3 1 I
(c) Ar— C— C— Ar (d) All of these
65. Which of the following will give Tischenko reaction? I l
CNH
(a) C6H5— CH 2— CHO (b) CH3— CHO
(c) C6H5— CHO (d) All of these 73. Benzoin condensation takes place in the presence of which
catalyst?
66. Which of the following reactions can be used for the formation of
new carbon-carbon bond between two molecules?
(a) C 2 H 5 O (b) CN
(a) Aldol condensation (b) Claisen condensation
(c) Reformatsky reaction (d) All of these (c) OH (d) Any one of these
67. Which one of the following reactions can be used for the formation 74. In the given reaction
of C— C— N bond in the molecule?
k c n /c 2h 5o h /h 2o
(a) Mannich reaction CH O product(s)
(b) Knoevenegal condensation
(c) Aldol condensation product(s) would be:
(d) Benzoin condensation
68. In which reaction hydrogen of carbonyl carbon transfers from one
(a) ^ C O S and CH ,OH
molecule to the carbonyl carbon of the other molecule?
(a) Aldol addition (b) Cannizzaro reaction
(c) Benzoin condensation (d) Reformatsky reaction HOHCN
69. P, y-unsaturated acids can be prepared by which one of the
following combinations?
(C) C— CHOH —
(a) C6H5— CHO + (CH3C0)20 (CH3COh° »
O O
C O O C ^s
(i) OH
(b) CH3— CH2— CHO +CH2
COOC 2H 5 (U)H /A v J - L O
O
CH2— COOC2H5 ( i) c 2H5ONa
75. In the given reaction
(c) CH3— C— CH3 + | .... HB /rH r00H)
|| CH2— COOC2H5 h ^o a CH3—CH 2— CHO + HCHO - ('.)concN^OH__>Product(s)
(excess) (ii)H 30

(i) (C jH jh N H
(d) CH3— CH2— CHO + B r- C H 2- C O O C 2H3 (ii) NH<C, ^ product(s) is/are:
(a) CH3— CH2— CH 2OH + HCOOH
70. In which reaction product formation takes place by formation of (b) CH3— CH— CHO
Y-lactone as intermediate compound?
CH2OH
(a) Perkin reaction (b) Stobbe condensation
(c) Favorskii rearrangement (d) All of these CH 2 OH
71. Arrange the given compounds in decreasing order of I
(c) CH3—C— CHO
electrophilicity
COOC2H5 CH2OH
H— COOC2H j ; | ; C2H50 — COOC2H5;
1 COOC2H5 ID CH2OH

(d) CH3— C—C H 2OH + HCOOH

CH2OH
76. A compound (X) C4H 8O which gives a 2,4-DNP derivative and a
positive iodoform test is:
O
Hint:
(a) CH 3— CHz— C— CH 3 (b) CH 3— CH 2— CH2— CHO
(c) CH 3—CH— CHO (d) All of these

CH 3
77. Compound [X], C4 H8O, which gives 2,4-DNP derivative and
negative haloform test is:

(a) CH — C— CH — CH (b) O - C H , OH
3 „OH 2
(c) (d) CH — CH— CHO
82. In the given reaction
3 I
CH, O O
78. Compound [X], whose MF is C 4H 8O gives positive haloform test
but gives no 2,4-DNP derivative, is:
OH
[X] will be:
I
(a) CH 2= C H — CH— CH 3 (b) CH 3— CH 2— CH2— CHO ONa OH
O ^OH
(a)
(c) c h 3 —c h 2— C— CH 3 »> □ "
79. Which of the following compounds are unstable and either exit as H H
an isomer or spontaneously decompose into other compounds: H O
(a) CH 3— C = C — OH
(b)

(b)
(c) CH
O
OH

3—CH- O— C H = C H — CH3
(c) CH3—CH—
(d) All of these
80. Arrange the following compounds in order of decreasing acidity
O
II
CH3—CH— C— NH2 ; CH3— (CH2)e— COOH (d) CH
I u
CH3
1
C6H5— CH3; C 6H5—OH.
It! IV
Select the correct answer from the codes given below: 83. In the given reaction
(a) II > IV > 1 > III O
(b) II > IV > III > I II (i) C iH jO N a
CH 3— CH 2— C— CH2— Br , > [X] _
(c) IV > II > I > III (ii)H jO
(d) III > I > IV > II
[X] will be:
81. Which hydrogen of the given compound is least acidic in nature? (a) CH 3— CH 2 — CH 2—C O O C ^ j (b) CH 3— CH— CH 3

COOQH5

A-
( 1) (c) Mixture of (a) and (b)
(2)
(d) CH 3— CH 2— CH2— COOH
( 1)
X ^ C H jO ) 84. Which one of the following 1,3-dicarbonyl compounds will not
W nH show enolisation?
(4) (4)
o 0 0
(a) I (b) 2 II II II
(a) CH 3— C— CH 2 — COOC 2H 5 (b) CH 3 — C— CH 2— C— CH 3
(c) 3 (d)4
 (B) is:
(c) only
O v J - o - chJ T ^
O O

(d) mixture of O - COOH and 0 - CH,OH

1
COOH ✓\,COOH O

( d ) f 99. In the given reaction

[Hint: The reaction is Favorskii rearrangement.

l ( ~ C—O— ^
0 Q 0 O O O

© [X] is:
(a) 50% NaOH (b) (C2H50)3A1
(c) (C2H50)2AIH (d) All of these
100. The unknown compound A, C6H i 20 meets the following criterion:
(1) It is optically active
(2) It racemices in the presence of base
(3) It forms hydrazone
(4) It gives iodoform test.
The structure of (A) is
O
96. In the given reaction
II
0 (a) CH 3— CH2— CH2— C— CH2— CH 3
1 (i) Br;/H® O
C H 3 - C H 2 — C— CH2— c h 3 9------- > [X]
(ii) OH II
(b) CH 3— CH 2— CH— C— CH 3
(iii) H 3O /H ®
CH 3
[X] is:
Br O O
I II II
(a) CH 3— CH— C— CH2— CH 3 (c) c h 3— c h 2— c h 2— c h 2— C— CH 3
(d) CH 3— CH 2— CH 2— CH 2— CH2— CHO
O
101. An unknown compound (A), C6H i 20 gives the following tests:
(1) 2,4-dinitrophenyl hydrazone
(b) (2) negative Tollens test
H,C- -CHj
(3) does not racemise in the presence of base
(c) CH 3 — CH— CH 2— CH 3 (4) on reductive aminatioii it gives 3-aminohexane.
The compound (A) is:
COOH
O
(d) CH 3— CH 2— CH 2— CH 2— COOH il
97. In the given reaction sequence (a) CH 3— CH2— CH 2— C— CH2— CH 3
Br2 CH1NH2 r„ , O
C6H5—CH 2— COOH pBr3) <ex^ [X]
. II
(b) CH 3— CH 2— CH— C— CH 3
[X] is:
Br Br O CH 3
O
(a) C 6H 5— CH—COBr (b) C6H5— CH— C— NHCH 3
II
O O (c) CH 3— CH 2— CH 2— CH 2— C— CH 3
o
(c) C6H5— CH— C— Br (d) C6H5— CH—C — NHCH 3 .c h 3 .
(d) CH 3— CH 2— C— CH
NHCH 3 NHCH 3 CH 3
\
98. Furfuraldehyde on treatment with conc NaOH followed by 102. An optically active compound (A) C 6H 12O 6 gives the following
acidification gives tests:
(1) Phenyl hydrazone formation
(a) only (2) Forms adduct *with NaHS03 and positive test with Tollens
t Q - C H;,OH reagent
(3) No racemisation with base
(b) only (4) On Clemenson reduction it gives 3-methyl pentane
COOH
The structure of the compound (A) is:
 o (a) an enolate (b) a Grignard reagent
II (c) an acetylide (d) a carbocation
(a) CH3— CH2— CH— C— CH3
(e) an enol
CH3 108. In a Michael reaction, addition to the a, P-unsaturated carbonyl
compound occurs in a:
(b) CH3— CH— CH2— CH2—CH O
(a) 1,2-fashion (b) 1,3-fashion
CH3 (c) 1,4-fashion (d) 1,5-fashion
(c) CH3— CH2— CH:— CH— CHO (e) Dieb-Alder reaction

CH3 Section-II

(d) CH3— CH:— CH— CH2— CHO Linked Comprehension based Questions (Q.No. 109 to 131)
In this section you have four short passages. After each passage
CH3
you will find several questions based on the passage. First, read
103. Which of the following underlined alpha hydrogens are the most passage-I, and answer the questions based on it. Then go to the next
acidic? passage.
O Passage-I : (Q.No. 109 to 114)

(a) CHj— CHO (b) CH3— C— CH2— CHO Hydrogen of a-carbon is acidic in character when functional group
is strong electron withdrawing group such as — N 02, — COOR, — CN
O O
etc. If a-carbon is present between two electron withdrawing groups,
the acidity of an a-hydrogen is even greater. Aldehydes and ketones
(c) CH3— C— Ort:—COOCH 3 (d) c h 3— c — c h 3
having a-hydrogen exist in solution as an equilibrium mixture of two
(e) CH3COOCH3 isomeric forms, the keto form and the enol form. The anions formed by
104. Which of the labeled hydrogen atoms in the given structure is the deprotonation of a-hydrogen bear most of the negative charge on
most acidic? oxygen and are referred to as enolate ions.
109. Which one of the following compound has minimum pK a value?
H—( O V tCH2— CH2—COOH (a) CH3— CHO (b) CH3— N 02
1 X Z J 3 4 5
O
H
1 (c) CH3— C - C H 3 (d) CH 3— COOC2H5
(a) 1 (b) 2 110. Which of these compounds contains active methylene group?
(c) 3 (d) 4
O
(e) 5 C O O C ^s
105. Which of the labeled hydrogen atoms in the given structure is the (a) CH3— C— CH:— COOC2H5 (b) CH2
COOC2H5
most acidic?
/C N
O (c) CH2\ (d) all of these
N 02
h- ^ ^ ^ h 2- c h 2^ c h 3
111. Which of these statements are correct for 2-methyl cyclohexanone?
(a) It can form two enolates
H (b) NaH/DMF forms thermodynamic enolate
2 (c) LDA/DMF forms kinetic enolate
(a) 1 (b) 2 (d) All are correct
(c) 3 (d)4 112. Carbonyl compounds having acidic hydrogen on a-carbon give
which of these reactions?
(e) 5
(a) Halogenation reaction
106. Which of the following is the most stable enol form of the given
(b) Deuterium exchange reaction
compound?
(c) Haloform reaction
Q. ^ .0 (d) All of these
113. Haloform reaction is given by:
O O •

(a) CH3— CH2—C — C H ^ - C —C H 2— CH 3

HO OH HO. .O H
(b) CH3— CH—C H 3
(a) « y y
NH2

HO O HO. ^ ,.0 O
(c) (d) II
(c) CH3— C— CHz— COOC2H5
(d) All of these
114. a-Halogenation reaction is given by:
107. What is the carbon nucleophile which attacks molecular bromine
in the acid catalysed a-bromination of a ketone?
 O
II -CHO +
f r - v h c -h Q
(a) CH 3— CH 2- C O O C 2 H 5 (b) CH3— CH 2— C— CH3
is :
(c) CH 3— CH— COOH (d) All of these
(a) Perkin reaction (b) Reformatsky reaction *
CH 3 (c) Knoevenagel reaction (d) Cannizzaro reaction
Passage-U : (Q.No. 115 to 122) 122. Which one of the following reactions takes place via formation of
zinc enolate?
Aldehydes and ketones give addition reaction and condensation
reaction with those compounds which have atleast one acidic hydrogen. (a) Reformatsky reaction (b) Knoevenagel reaction
The reaction is mainly catalysed by base. Two steps are common in (c) Perkin reaction (d) Wittig reaction
these reactions. The first step is the formation of stable carbon Passage-Ill (Q.No. 123 to 126)
nucleophile and the second step is the nucleophilic addition reaction of
Ester gives nuclophilic addition reaction followed by elimination
aldehyde or ketone with carbon nucleophile.
reaction with carbon nucleophile. When carbon nucleophile is of an ester
115. In the given reaction
then the reaction is known as Claisen condensation reaction. This
OH reaction is also carried out between ester and a ketone. A successful
Base Claisen condensation requires an ester with two a-hydrogens and an
c h 3— c h o +c h 3— z * CH 3— CH— CH 2Z
equivalent amount of base rather than a catalytic amount of base.
CH3Z may be:
123. Consider the given reaction
(a) CH3CHO (b) CH3N 0 2
C 2H5ONa
(c) CH 3 - C O C H 3 (d) all of these CH 3— COOC 2 H 5 - ■
*enolate ion (A)
c 2h 5o h

116. The given reaction

Ester ( X )
OH (A)- * Product
Claisen condensation
O H/HOH I
CH3— CHO + CH 3— CHO- CH3— CH— CH 2— CHO For the above reaction the most reactive ester is:
is known as: O O
(a) Aldol addition (b) Aldol condensation
(d) Claisein-Schmidt reaction (a) C 6 H5COOC 2 H 5 (b) C 2H5 O - C — C— OC 2 H5
(c) Claisen condensation
117. The given reaction O
II
(c) HCOOC 2 H 5 (d) C 2 H 5 O - C — OC 2 H5
CH3— CHO + CH 3— CH2— CHO /H° H ■
>
OH [Hint: The second step is nucleophilic addition reaction of
I carbanion on carbonyl carbon. Thus more the electrophilicity of
CH 3— CH— CH— CHO + three more products carbonyl carbon, more is its reactivity.]
124. Intramolecular Claisen condensation given by diester is known as:
is an example of: CH 3
(a) aldol condensation (a) Stobbe condensation (b) Dieckmann condensation
(b) mixed aldol addition (c) Mannich reaction (d) Reformatsky reaction
(c) mixed Claisen Schmidt reaction 125. In the given reaction
(d) Perkin reaction O
118. The given sequence of reaction
OH C 2H 5 O—C — (CH2)3— CH 2— COOC 2H 5
LD A (i) CH3CH2CHO I
CH3— CHO ■
»CH 3— CH 2— CH— CH2—CHO
DMF (ii) HOH (i) C .H sO N a/C jH jO H
4[X]
(ii) H2O/HCI
is known as: [X] is:
(a) aldol addition (b) mixed aldol addition
9 o
(c) Directed aldol addition (d) Intermolecular aldol addition
119. Intramolecular aldol addition is given by: —CH,
(a)
(a) 1,4-dicarbonyl compounds
O
(b) 1,5-dicarbonyl compounds
(c) 1,6 and 1,7-dicarbonyl compounds HO
(C )
(d) All of these
120. Which one of the following is correct for Claisen-Schmidt 126. In the given reaction
reaction? ■
(a) The reaction takes place between two molecules of aldehydes. O
(b) The reaction takes place between aromatic aldehyde and
aliphatic ketone
(c) The reaction takes place between two molecules of ketones
+X
C r
(d) The reaction takes place between two molecules of aromatic
[X] is:
aldehydes.
121. The name of the given reaction
 o Reason (R). You are to examine these two statements carefully and
decide if the Assertion (A) and the Reason (R) are individually true and
(a) H— C—Cl (b) HCI + CO if so whether the reason is a correct explanation of the Assertion. Select
COOC 2H 5 your answer to these questions using the codes given below and give
(c) HCOOC 2 H5 (d) I your answer accordingly.
COOC 2H 5 Codes:
(a) Both A and R are true and R is the correct explanation of A
Passage-IV : (Q.No. 127 to 131)
(b) Both A and R are true but R is not a correct explanation of A
Aldehyde having no a-hydrogen when treated with strong base, (c) A is true but R is false
undergoes redox reaction. This reaction is known as Cannizzaro (d) A is false but R is true
reaction. Tischenko reaction is also a redox reaction, which takes place 132. (A): Compound [X] is more basic than compound [Y]
in the presence of aluminium ethoxide.
127. Which of these compounds will give Cannizzaro reaction?
(a) C6H5— CH 2— CHO (b) CHO— CHO
(C) C6H5— CH—CHO (d) all of these
O O
CH 3 (X ) (Y )

128. Intramolecular Cannizzaro reaction is given by: (R): More is the stability of conjugate acid of the base, greater
is the basicity of base.
CHO
[Hint: Basicity of base can be known by stability of conjugate
acid of the base.

CHO CHO —
(c) CHO—CHO (d) All of these
129. Internal crossed Cannizzaro reaction is given by: O © O —H
X
(a) C6H 5COCHO (b) C 6H 5 CHO arom atic highly
(highly basic)
stable
(c) CHO— CHO (d) C6H5—CH 2CO— CHO
130. Consider the following reaction
CH 2OH
(i) HCHO (excess)/NaOH
c h 3— c h o 4 CH 2 OH— c — c h 2o h + HCOOH
(ii) H2O/HCI
c h 2o h

This is an example of:

(a) Aldol addition
(b) Cannizzaro reaction
(c) Aldol addition followed by crossed Cannizzaro reaction
(d) Tischenko reaction
131. In the given reaction O— H OH
n on -arom atic

/ H U : : HO + ^ ^ — CHO le ss stable
th an (T )
O
| N a ,[ F e (C O )J 133. A Tropolone [X] is much more basic than most of the
a, P-unsaturated ketones (Y)
Product
the product(s) is/are:

(a) 1 / c h 2o h on'y (Y)

O

(b) ooh on|y (R): Conjugate acid of tropolone is less stable than the conjugate
acid of a, P-unsaturated ketones.
(c) mixture of (a) and (b)
134. (A): 1,3-dicarbonyl compounds are such as (X) are usually
O mosdy enolised.

(d) O
o II
CH 3— C— CH 2— COOC 2H 5
Section-Ill
x
Assertion and Reason (Q.No. 132 to 137)
Directions (Qs. 132 to 137): These questions consist of two (R): Enol form of 1,3-dicarbonyl compounds is delocalised over
statements, one labelled the Assertion (A) and the other labelled the five atoms.
 [Hint: (B) Wittig reaction (2) (C6H5)3P = C H 2
(C) Benzoin condensation (3) conc. NaOH
O O (D) Cannizzaro reaction NH2NH2/KOH
(4)
II II Codes:
CHj— C— CH2— C— 0 C 2HS
A B C D
(a) 1 2 3 4
(b) 4 2 1 3
© © © (c)2 4 1 3
O— H O C o — H---O (d) 2 4 3 1
I I © II I . .
141. Match List-I with List-II and select the correct answer from the
CH,— C = C H — C = 0 — C,H, CH,-C-r-CHf=Cr—OC,H,
3 Ky 2 5 codes given below the lists:
List-I List-II
135. (A): Cannizzaro reaction is given by aldehydes having no (compound) pka
a-hydrogen atom.
O
(R): Cannizzaro reaction is Redox reaction.
136. (A): Directed aldol addition reaction is carried out in presence of (A) CH3— C— CH 2— COOC2H5 (1) 17
very strong base such as LDA.
o o
(R): In directed aldol addition reaction no cross over product is
formed. (B) CH j— C— CH2— C— CH3 (2) 8.9
137. (A): Perkin reaction is given by aliphatic aldehydes.
(C) CHO— CH2— CHO (3) 10.7
(R): Product of the reaction is a, (}-unsaturated acid.
(D) CH3— CHO (4) 5
Section-IV
Matching Type Questions (Q.No. 138 to 142) A B C D
138. Match List-1 with List-II and select the correct answer from the (a) 3 2 1 4
codes given below: (b) 3 2 4 1
List-I List-n (c) 2 3 1 4
(A) Hell Volhard Zelinsky (1) a-hylogenation of acids (d) 1 2 3 4
(B) Reformatsky reaction (2) Preparation of |3-hydroxy esters 142. Match Column-I with Column-II
(C) Claisen condensation (3) Preparation of (3-hydroxy Column-II
aldehyde (p) CH3— CHO
(D) Aldol addition (4) Preparation of p-ketoesters (q) C6H5CHO
Codes:
(r) Br— CH 2— COOC 2H 5
A B C D
(a) 2 1 3 4 (s)
(b) 2 1 4 3 ° , n - < 5 ^ h o

(c) 1 2 4 3
Column-I
(d) 1 2 3 4
(a) Reformatsky reaction
139. Match List-1 (reaction) with List-II (name of the reaction) and
select the correct answer using the codes given below the lists: (b) Aldol condensation
List-I (c) Benzoin condensation
(d) Cannizzaro reaction
20% NaOH
2CSH«CH0
"6n 5'“ Section-V
Statements (Q.No. 143 to 146)
CftH,CHO + H C H O - ^ ^ 143. Consider the following statements regarding the following
K C N /C ,H ,O H reaction:
(C H jC O h O H20
(C) 2C6H5CHO c 6h 5c h o
C H 3C O O N a A
C H 3COO Na I C6H5— C H = C H — COOH + CH3COOH
(D) C6H5C H 0 + (CH3C 0 )20
(1) The reaction is a Perkin reaction
List-II (2) The anhydride having atleast one a-hydrogen, provides an
(1) Benzoin condensation enolate for the reaction
(2) Cannizzaro reaction (3) The acetate deprotonates the anhydride to form the nucleophile
(3) Cross cannizzaro reaction needed for the reaction. .
(4) Perkin reaction Which of the above statements are correct?
Codes: (a) 1,2 and 3 (b) 1and 2
A B C D (c) 2 and 3 (d) 1and 3
(a) 1 3 2 4 144. Consider the following statements about p-diketones:
(b) 2 3 1 • 4 (1) They show keto-enol tautomerism
(c) 1 3 4 2 (2) The enol form is capable of forming an intramolecular
(d) 2 3 4 1 hydrogen bonding
140. Match List-I (Reaction) with List-II (reagent) and select the correct (3) The methylene group flanked by two carbonyl groups can be
answer using the codes given below the lists: easily deprotonated.
List-I List-H Which of the statements given above are correct?
(A) Wolf-kishner reduction (1) NaCN/C2H5OH
(a) 1 and 2 (b) 1and 3
 (c) 2 and 3 (d) 1,2 and 3 [Hint: Compound(l) is totally enolised because enol form is
145. Consider the following reaction sequence: stabilised by delocalisation. Compound (2) on enolisation will
convert into antiaromatic compound which is highly unstable.
CH3—CHO +C H a - C H O ^ ^ CH3—C H = C H —CHO Hence compound (2) exists only in keto form.
Firs! step

/ o —
NH—CH3
Which one of the following is not correct? 0 ^ 0
(a) The first step is aldol addition
(b) The first step is aldol condensation 1
(c) The second step is Micheal addition reaction
(d) The second step is 1,4-conjugate addition
ffi• KJ
0 * 0U

146. Consider the following statements: H O - ^ b > A ^ o h

(1) 1,3-dicarbonyl compounds such as ethyl acetoacetate are
1
usually mostly enolised.
(2) The given compound (1) exists mainly in enol form (100%)
\ t
t
V " X /
® o ^ o 0 0©
' 0 * 0

—^ O ©
H
( 1)

(3) The given compound (2) exists only in keto form

ho - <0 ~
antiaromatic
H
o=0 = ° II
(2)
Of these statements:
(a) only 1 is correct (b) 1 and 3 are correct
(c) 2 and 3 are correct (d) 1,2 and 3 are correct

Section-I

4. (a) 5. (c) 6. (d) 7. (b) 8- (c) 9. (c) 10. (c)

1. (d) 2. (b) 3. (b)
13. (c) 14. (a) 15. (d) 16. (b) 17. (a) 18. (d) 19. (c) 20. (d)
11. (b) 12. (d)
23. (a) 24. (d) 25. (a) 26. (b) 27. (d) 28. (a) 29. (a) 30. (b)
21. (a) 22. (d)
33. (d) 34. (b) 35. (c) 36. (c) 37. (d) 38. (c) 39. (b) 40. (d)
31. (c) 32. (a)
43. (d) 44. (d) 45. (a) 46. (a) 47. (b) 48. (d) 49. (a) 50. (a)
41. (c) 42. (c)
53. (d) 54. (c) 55. (d) 56. (c) 57. (c) 58. (c) 59. (d) 60. (a)
51. (b) 52. (d)
62. (d) 63. (d) 64. (d) 65. (d) 66. (d) 67. (a) 68. (b) 69. (c) 70. (b)
61. (a)
73. (b) 74. (c) 75. (d) 76. (a) 77. (d) 78. (a) 79. (d) 80. (a)
71. (a) 72. (d)
84. (d) 85. (a) 86. (b) 87. (c) 88. (a) 89. (b) 90. (a)
81. (b) 82. (c) 83. (c)
94. (b) 95. (c) 96. (c) 97. (d) 98. (d) 99. (b) 100. (b)
91. (a) 92. (a) 93. (a)
102. (d) 103. (c) 104. (e) 105. (c) 106. (d) 107. (e) 108. (c)
101. (a)
111. (a)

Section-II • >«.

111. (d) 112. (d) 113. (d) 114. (d) 115. (d) 116. (a) 117. (b) 118. (c)
109. (b) 110. (d)
121. (c) 122. (a) 123. (b) 124. (b) 125. (a) 126. (c) 127. (b) 128. (d)
119. (d) 120. (b)
129. (a) 130. (c) 131. (d)

S ection - Ill

132. (a) 133. (c) 134. (a) 135. (b) 136. (b) 137. (d)

Section-IV

138. (c) 139. (b) 140. (b) 141. (b) 142. a— i b— p; c— q, r; d— q, s

Section-V

143. (d) 144. (d) 145. (a) 146. (d)