Carbonyl Compounds

FINAL TOUCH
REVISION
OF
ORGANIC CHEMISTRY
FOR JEE ADVANCED
BY
NAVNEET JETHWANI
CARBONYL
COMPOUND
ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar,
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA F.T.R. BY N.J. SIR
Single Choice Questions
O Cl O
O N 2H 4 /KOH/H 2O
  (A) ; Product A is :
1. (Wolf Kishner reduction)
major
NO2
Cl O
OH O
O
O
(A) (B)
NO2
NO2
Cl OH
O O
(C) (D)
NO2 NO2
Ans. (A)
O
C CH3 CH2 CH3
2.
 
CH2 CH2 NMe3 CH2 CH2 NMe3
Above conversion can be achieved by :
(A) Wolf-Kishner reduction (B) Clemmensen reduction
(C) LiAlH4 (D) NaBH4
Ans. (B)
O CH2 CH3
CH2 CH3 CH2 CH3
C CH3 (A)
Hg)
Zn(
l
HC
3. NH
2
NH
OH – 2
/ (B)
OH Cl Cl
OH (P) (Q) (R)
Identify product (A) & (B) from the given product P, Q, R :

(A) A = P, B = Q (B) A = Q, B = R (C) A = Q, B = P (D) A = R, B = P
Ans. (C)
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 2
O
C CH3
Zn (Hg)
4. 
HCl
(A) ; Identify the A.
HO
CH2 CH3
(A) (B)
HO Cl
OH
(C) (D)
Cl
Ans. (B)
5. Increasing order of equilibrium constants for the formation of a hydrate :
O O O
O
NH2
NH2 O2N
(I) (II) (IV)
(III)
(A) IV < III < II < I (B) IV < III < I < II (C) I < II < III < IV (D) II < III < I < IV
Ans. (C)
HgSO4
6. C C OCH3 
dil.H2SO4
 (A) Product (A) is
Major product
O
(A) C CH2 OCH3 (B) C CH2 OCH3
OH
O
(C) CH2 C OCH3 (D) CH2 CH OCH3
OH
Ans. (C)
H 3O 
7.   A  B . Compound (A) and (B) can be differentiated by :
O
(A) 2-4-DNP (B) Fehling solution (C) Lucas reagent (D) NaHSO3
Ans. (B)
OH
OH
OH OH
8. PCC (excess) 1 equivalent CH3MgBr NaBH4
(A) (B) +
(C) (D)
H+ H3O
Product (D) will be
OH OH
OH
CH CH3
(A) (B) OH
OH OH
OH
(C) OH (D)
Ans. (B)
9. Rank the following in order of increasing value of the equilibrium constant for hydration, Khyd. (smallest value first)
O
O
O (CH3)3CCC(CH3)3
(1) (2) (3)
(A) 1 < 2 < 3 (B) 3 < 1 < 2 (C) 2 < 1 < 3 (D) 2 < 3 < 1
Ans. (B)
+i ve Iodoform test
–ive Tollens test

10.
H2 O
C6H12O3 Positive Tollens test
drop of H2SO4
A
Compound (A) is :
O O OCH3
(A) CH3 – C – CH – CH 2 (B) CH3 – C – C – CH3
O O
(C) CH3 – C – CH2 – CH – OCH3 (D) H – C – CH 2 – CH2 – CH – OCH 3
Ans. (C)
CH2
11. CH3 CH CH CH2 OH 
HCHO
(A) ; Product (A) is
TsOH, 
OH
CH3
Ph CH2 Ph CH Ph CH3
CH3 CH3 Ph
(A) (B) (C) (D)
O O O O O O O O
Ans. (B)
HgSO4
12. CH3  C  CH 
dil.H2SO4
 (A)
(1)BH 3 .THF
CH 3  C  CH 
(2)H O / HO 
 (B)
2 2
Product (A) and (B) is differentiated by :

(A) 2-4-DNP (B) NaOI (C) Na-metal (D) NaHSO3
Ans. (B)
HCN LiAlH4 NaNO2

13.  (A)  (B) 
HCl
(C)
End product (C) in above reaction is :-
OH
O O O OH CH
2
(A) (B) (C) (D)
Ans. (A)
14. Which of the following pairs of reactants is most effective in forming an enamine ?
O
O
||
(A) CH3CH 2 CH[(CH3)2 CH]2 NH (B) + CH3 – NH – CH3
O
||
(C) (CH 3 )3 C CH  (CH 3 ) 2 NH (D) None of these form an enamine
Ans. (C)
OH
H3O
15.   Products ; Product of the reaction is / are :
O
O CH2
OH
OH
(A) (B) OH (C) HCHO (D) Both (A) and (C)

OH
OH
OH
Ans. (D)
16. Which of the following does not form a stable hydrate on addition of H2O ?
O
O O O
(A) Ph C C C Ph (B) O
(C) O (D)
Ans. (D)
17. Consider the following sequence of reactions.
H
1.C 2 H 5 MgBr H 2SO 4 ,heat 1.O 3
Ketone A 2.H 2 O
 B 
 H 2O
C 
2.Zn,H 2O
 + O
O
The ketone (A) is
(A) (B) (C) (D)

O O O O
Ans. (B)
18. In the reaction,
EtONa/EtOH
+ CH3COCH3 
heat
 X , the product (X) is
H3C CH3 H3C CH3
OH
(A) (B)
CH3
CH3 C
(C) C (D)
CH3 CH3
Ans. (B)
19. Which of the following -keto carboxylic acid does not undergo decarboxylation on heating ?
CO2H
(A) (B)
O
CO2H O
CO2H
CH3
(C) (D) None of these
O
Br
Ans. (A)
O
PCC H 2C  CHMgBr NH 4Cl/H2O
20. HOCH 2CH 2CH 2 C OCH 2CH 3  (A) 
(1molar equivalent)
(B)  (C)
O
KOH H3O (CH3 C)2 O

 H 2O
 (D)
Pyridine
Product (D) is :
O
O C CH3 O
(A) H2C CH CH CH2 CH2 C OH (B) H2C CH CH2 CH CO2H
OH
O O O
CH CH CH2 C O C CH3
(C) H2C CH2 (D) H2C CH CH2 CH CH2 C O H
OH OH
Ans. (C)
21. The final product of the following sequence of reaction is :
H3O 
Mg H2C  O
(CH3O)2CHCH2CH2CH2Br   
heat

O O
(A) CH 3O C CH 2CH2CH 2CH 2OH (B) CH3 C CH2CH2CH2CH2OH
O O O
(C) HC CH 2CH 2CH 2CH 2OH (D) HC CH2CH2CH 2CH
Ans. (C)
22. The amino ketone shown below undergoes a spontaneous cyclization on standing. What is the major product of
this intramolecular reaction ?
O
CCH3
CH2CHNH2
CH3
O CH3
N
(A) (B)
CH3 CH3
CH3 CH3
N
(C) (D)
NH2 CH3
Ans. (D)
MgBr
NH4Cl HCl(conc.) KOH(4 molar)
23. O (N) 
H2O
(O) 
cold
(P) 
ethanol, 
(Q)
Product (Q) will be :
(A) (B) (C) (D) OH
Ans. (B)
O

NH 2 OH H LAH
24.  (A)  (B)  (C) ; Product (C) of the reaction is :
OH
(A) (B) (C) (D)
N N N O OH
N
H H H H
Ans. (B)
25. C N + CH3MgBr 

H O
NaOI
(A)  (B)  (C)
14 3
Product (A) and (C) is :
O O
14
(A) C CH3 ; CHI3 (B) C CH3 ; CHI3
O
(C) C CH3 ; CHI3 (D) CH2 CHO ; CHI3
14 14
Ans. (C)
OH
PCC
(A)
26.
OH PCC
(B)
(A) and (B) is differentiated by :

(A) NaH (B) 2-4 DNA (C) Tollen’s reagent (D) NaHSO3
Ans. (C)
 NH2  NH 2 heat
27. CH2 CH2 CO2H 
BaCO 3
 A   B 
KOH
(C) , Product (C) obtained is :
CH2 CH2 CO2H
(A) CH3 – CH = CH – CH2 (B)
N NH2
(C) (D)
Ans. (C)
O O
KOH
28. + CH2 = CH – CH2 – Br   (A) ; Product (A) is :
(75%)
CH2 CH CH2
O O CH2 CH CH2 O O
(A) (B)
O O
O O
(C) (D)
CH2 CH CH2
CH2 CH CH2
Ans. (B)
29. End products of the following sequence of reactions are :
1.I2  NaOH, 
 2.H 

3. 
C CH3
O O
(A) yellow ppt. of CHI3, (B) yellow ppt. of CHI3,
COOH CHO
O
COOH
(C) yellow ppt. of CHI3, (C) yellow ppt. of CHI3,
COOH
Ans. (C)
CO2Et
H3O 
30. 
 A ; Product obtained is :
EtO2C
O
O O OH
CO2Et
(A) (B) (C) (D) None of these
O
O O
Ans. (B)
NH 2OH H 2SO4 H3O CHCl3 

31. (A) 

(B)  (C)  (D)  (E) 
KOH, 
 CH 3  N  C
Ph Ph

SOCl 2 (i)PhMgBr (excess) H CH2I 2
(D)  (F) (ii)H 
(G) 

(H) 
Zn/Cu

Molecular weight of compound (A) is :

(A) 58 (B) 120 (C) 60 (D) 182
Ans. (A)
32. Compound A and B, both were treated with NaOH, producing a single compound C.
O O
CH3 CH3
HO– Compound (C) is :

+ heat
OH OH
(A) (B)
O
O C – CH3
(A) (B)
O
O
(C) (D)
Ans. (A)
O O –
|| || HO / 
33. CH3 – C – CH2 – CH 2 – CH 2 – CH 2 – C – H (A) ; Product (A) is :
(73%)
O
O
C – CH3
(A) (B)
O
CH3
C – CH3
(C) (D)
CHO
Ans. (B)
34. Ph – CH = CHCHO + CH3CH = CHCHO

base (A)87% ; Product of this reaction is :
EtOH, 
(A) Ph –(CH = CH)2 – CHO (B) Ph – (CH = CH)3 – CHO

(C) Ph – (CH = CH)4–CHO (D) Ph – CH = CH – CH = CH – CH3
Ans. (B)
10% NaOH H2
35. CH3CHO 5°C  Ni (A) ; Product (A) of the reaction is
(A) propanol (B) ethanol
(C) butanol (D) pentanol
Ans. (C)
O
||
LDA (A) ; Product A is :
36. CH3 – CH2 – I (major)
O O
|| ||
(A) (B)
O O
|| ||
(C) (D)
Ans. (B)
37. The reaction,

CHO
+ conc. NaOH , products Identify the product.
CHO
CH(OH)2
(A) (B) O
CH(OH)2
–
CH2OH COO
(C) (D)
– –
COO COO
Ans. (C)
38. Identify the principal product of the following reaction ?
CH2CH = O
NaOH
H2O + ?
ethanol, water, heat
CH2CH = O
CH = O CH = O
(A) (B)
CH = O
OH O
(C) (D)
OH O
Ans. (B)
O O
39. CH3 – C – CH2 – CH2 – CH2 – CH2 – C – H
KOH
Number of intramolecular aldol condensation product is :

(A) 1 (B) 2 (C) 3 (D) 3
Ans. (C)
–
OH 
40. CH 3CH = CHCHO Aldol (A); Product A is :
condensation
(A) CH3(CH = CH)3CHO (B) CH3CH2CH2(CH = CH)2CHO

(C) CH3(CH2CH2)3 CH = CH – CHO (D) none is correct
Ans. (A)
OH
H+ O3 HO–
41. 
(A) Zn
(B)  (C) ; Product (C) is :
O
O
(A) (B)
CHO
(C) (D)
O
C – CH3
Ans. (C)
42. Which of the following reactant on reaction with conc. NaOH followed by acidification gives the following lactone
as the product ?
O
C–OCH3 CO2H
(A) (B)
CO2H CHO
CHO CO2H
(C) (D)
CHO CO2H
Ans. (C)
O
43. (P)
KOH

KOH
(Q) 

 Ph–CH2–OH + Ph – CO 2
(R) 
O3
 P + Q, Structure of (R) is
CH3
(A) Ph – CH = CH – CH3 (B) Ph – CH = C
CH3
CH3 CH3
(C) Ph–C = CH–CH3 (D) CH3–C=CH2
Ans. (B)
44. The following reaction gives :
CHO
conc.NaOH
+ HCHO ?
OMe
OMe
CH2OH CH2OH
(A) + CH3OH (B) + HCO2

OMe OMe
OMe OMe
COOH COOH
(C) + HCOOH (D) + CH3OH

OMe OMe
OMe OMe
Ans. (B)
45. Arrange these compounds in decreasing order of reactivity for the nucleophilic attack:
(I) Acid chloride (II) Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below :
(A) I > II > III > IV (B) IV > III > II > I (C) III > II > I > IV (D) I > IV > II > III
Ans. (A)
46. In the given reaction
O O
[X] (i)LiAlH 4
CH3 CH2 C CH2 COOC2H5 [A] CH3 CH2 C CH2 CH2OH+C2H5OH
(ii)H2O/H
[X] will be :
CH3 OH CH3 OH
(A) HCHO (B) (C) (D) HCN
CH3 OH +H CH3 OH +OH
Ans. (B)
47. In the given reaction:


NH2 OH/H
C6H5 C H [X]
[X] will be:

(A) Only syn oxime (B) Only anti oxime
(C) Mixture of syn and anti oxime (D) Secondary amide
Ans. (C)
48. Number of aldol products (without counting stereoisomers) in the given reaction :
C6H5CHO + CH3 – CHO OH Product

will be :
(A) One (B) Three (C) Two (D) Four
Ans. (C)
49. In the given reaction
OH
NaOH
X+Y CH3 CH CH CHO
5°C
CH3
(X) and (Y) will respectively be :

(A) CH3–CH2–CHO and CH3–CH2– CHO (B) CH3–CHO and CH3–CH2–CHO
CH3
(C) CH3–CHO and CH3–CHO (D) CH3–CHO and CH3 C CHO
CH3
Ans. (B)
50. Acetophenone can be obtained by the distillation of :
(A) (C6H5COO)2Ca (B) (CH3COO)2Ca
(C) (C6H5COO)2Ca and (CH3COO)2Ca (D) (C6H5COO)2Ca and (HCOO)2Ca
Ans. (C)
51. The given reaction :
(i) Zn
C6H5–CHO + Br–CH2–COOC2H5 CH CH CH COOC2H5
(ii) HOH/NH4Cl 6 5
(iii)
is known as :
(A) Perkin reaction (B) Knoevenagel reaction

(C) Reformatsky reaction (D) Claisen Schmidt reaction
Ans. (C)
52. The Product of the reaction :
O2N CHO + (C6H5 CH2CO)2O

C6H5 CH2COONa/
[X]
will be :
(A) C6H5 CH CH COOH (B) NO2 CH CH COOH
(C) C 6H 5 CH C COOH (D) NO2 CH C COOH

CH 3 C6H5
Ans. (D)
53. In the given reaction :
NaBH4 (X) (i) BH3 (Y)

H2C O (ii) H2O/H+(excess)
(X) and (Y) are :
(A) CH2 OH and HOCH 2 O
(B) CH 3 O and HOCH2 O
(C) CH 2 OH and CH3 OH
(D) CH2 OH and CH3 O
HO
Ans. (C)
54. A compound with molecular formula C8H18O4 does not give litmus test and does not give colour with 2,4–DNP. It
reacts with excess MeCOCl to give a compound whose vapour density is 152. Compound A contains how many
hydroxy groups ?
(A) 1 (B) 2 (C) 3 (D) 4
Ans. (C)
55. O
(i) NaBH4
A+ B
(ii) H2O
Identify relationship between A & B Products ?

(A) Diastereoisomers (B) Enantiomers (C) Positional isomers (D) Identical
Ans. (A)
56. In the reaction sequence
HSCH2CH2SH H2
O +
A Ni, heat B
H
The products (B) is :
(A) (B)
S
SH
(C) (D) S
SH
Ans. (B)
57. Which of the following does not form a stable hydrate by the addition of H2O ?
O O O
(A) Ph C C C Ph (B)
O
(C)
O (D)
Ans. (C)
58. The conversion
O O
O
can be effected by using the reagent

(A) Tollen’s reagent (B) O3
Cl CO2H Cl CO3H
(C) (D)
Ans. (D)
O O
NaOH
+ Cl2 P CH3COOH
59. (I) (II) + Cl2 Q
1 :1 1 : 1
(mole) (mole) (mole) (mole)
Organic product P & Q are respectively -
O O O O
Cl Cl Cl Cl
(A) , (B) ,
O O O O
Cl Cl Cl Cl
(C) Cl , (D) Cl , Cl
Ans. (C)
60. Total number of stereoisomers of major product (Q) are
NaOH 2CH3 CHO
CH3 CHO + 4HCHO -HCOONa (P) (Q)
H
(A) 0 (B) 4 (C) 8 (D) 2

Ans. (D)
61. The compound having the highest dipole moment is :
O
(A) (B) O (C) O (D)
O
Ans. (B)
62. Final product in the given reaction sequence is :
O
PhMgBr
+ [A] (i) H-C-H
H2
CH3 CH CH 
[B] [C]
(ii) H Pd/BaSO4
H
OH
(A) (B)
H H H OH
OH OH
(C) (D)
H H H H
Ans. (D)
63. Consider the following reaction sequence.
1. O3 NaOH
A B
2. Zn.H2O heat
The products (A) and (B) are, respectively.

O
OH
(A) and
O
OH
OH
(B) and
OH
O
O
(C) and
O
O O
OH
(D) and OH
O O
Ans. (C)
64. Consider the following sequence of reactions.

O
HOCH2CH2OH 1. LiAlH4/Et2O
+ A + B
H 2. H 3O
COOCH3
The products (A) and (B) are, respectively.
O O
O O O
(A) and (B) and
O
COOCH3 CHO
CH3OC COOCH3
O
O O O OCH2CH2OH OCH CH2
(C) and (D) and
COOCH3 CH2OH COOCH3 CH2OH
Ans. (C)
65. In the reaction
O O
Me
1. KOH. heat The product X is

2. H 3O+
Me COOH Me COOH
(A) (B)
HOOC HOH2C
HO COOH O
Me Me
(C) (D)
Ans. (C)
O
H
+
(i) N 2O 4
Q H3 O+ R
HCHO(excess)
S;
66. + C3H8O2 (leq.) P – Ba(OH)2
O optically inactive (ii) OH /
diol
Final product ‘S’ is -
OH
OH
(A) (B)
HO
OH
OH
OH
(C) (D)
HO
Ans. (B)
O –
OH CH3 MgBr Zn-Hg
67. heat
A
CuBr
B
conc. HCl
C the product ‘C’ is
O
(A) (B) (C) (D)
Ans. (C)
68. Consider following intramolecular aldol condensation reaction :
O
–
OH
X ; X can be :

(A) (B)
O O O O
O O
(C) (D)
O O
Ans. (D)
69. CH3CH = CHCHO OH
–
 A, A is :
aldol
(A) CH3(CH = CH)3CHO (B) CH3CH2CH2(CH = CH)2CHO

(C) CH3(CH2CH2)3CH=CH – CHO (D) None is correct
Ans. (A)
70. Which one of the following will undergo aldol reaction most readily.
O O
O O
(A) (B) (C) (D)
O
O
Ans. (A)
O
H2 HCHO
71. Ph – C – Cl Ph – CHO (C) + (D)
Pd – BaSO4 ,KOH
Product (C) & (D) are :

(A) Ph–CO2H, Ph–OH (B) Ph  CO 2 , HCO 2
(C) Ph  CH 2 OH, H  CO 2 (D) Ph  CO 2 , CH 3OH

Ans. (C)
CHO
conc. NaOH H+ (B)
72. (A)

CHO
Product (B) is
O O
O C CH2–O–C
(A) H2C=CH–CO2H (B) CH2 CH2 (C) (D) H2C=C=O
CH2–O–C
C O O
O
Ans. (B)
+
Aq. OH Conc. OH
73. PhCOCHBr2 A B H ; the compound ‘C’ is :
(A) PhCH(OH)CHO (B) PhCH(OH)COOH
(C) PhCOOH (D) None of these

Ans. (B)
O OH
-
A : Ph – C – CH = O B : Ph – C – COO C : Ph – CH – COOH
H OH
O O
NaOH KMnO4 NaOH/CaO
74. C C H A B C ; Product ‘C’ is
(conc.) 
O
CHO
(A) (B) (C) (D)
Ans. (A)
OH
A : Ph–CH–COONa B : PhCOOH C:
O
CCH
1% HgSO4/Dil.H2SO4 12/ NaOH 
75. +
X; X is :
H
O O O O
COOH COCH3 CH2CHO
(A) (B) (C) (D)
Ans. (D)
O O O
C–CH3 COOH
HgSO4 I2/NaOH 
+
H2SO4 H –CO2
O
P2O5 (i) CH3MgBr (i) I2 + Ca(OH)2
76. C – NH2 A (ii) H O+ B (ii) C;
 3 
(iii) –CHI3
O O
(A) C – NH2 (B) C – OH
(C) C (D) C – CH2CH3

O O
Ans. (C)
O
A: CN B: C – Me
77. The major product pair of the following reaction will be :
CHO
HCHO Products
NaOH(aq)
COONa CH2OH
+ CH3OH + HCOONa
(A) (B)
CH2OH COONa
+ CH3OH
(C) (D) +
HCOONa
Ans. (B)
78. Reactant ‘X’ will be :
CH 2OH
– +
COO Na
H+ O3
X Y Z1 + Z2 NaOH +
 Zn
OH/
Ph – C = CH – C – Ph
CH3 O
OH OH
(A) Ph – CH – CH – Ph (B) Ph – CH – CH – CH 3
CH 3 Ph
CH 3 OH OH
(C) Ph – CH – C – Ph (D) Ph – CH 2 – CH – Ph
CH 3
Ans. (A)
OH
X : Ph–CH–CH–Ph Y : Ph–C=CH–Ph Z1 : Ph–C–Me Z2 : Ph–CHO
CH3 OH O
79. Which is reduced during cannizaro’s reaction of HCHO & PhCHO with 50% conc. NaOH
(A) H C H (B) Ph C H
O O
(C) Both H C H and Ph C H (D) NaOH

O O
Ans. (B)
Mg  Hg conc.H 2SO4
80. 2Ph C C Ph 
H2O
 
Product
O O
The main product is :
Ph Ph
(A) Ph C C Ph (B) CH3 C C CH3 (C) Ph C C CH3 (D) Ph C C CH3
O O O O CH3 O O CH3
Ans. (C)
81. Which of the following will not undergo Cannizaro reaction
CHO
(A) (B)
O CHO Cl
CHO
(C) (D) Cl3C–CHO
Ans. (D) Carbonyl
O3 conc.KOH

Zn
(A)  (B)
82. (1mole)
End product (B) of above reaction is
CHO CO2 K

(A) (B)
CH2OH CH2OH

CH2OH CO2 K
(C) (D)

CH2OH CO2 K
Ans. (B)
83. Product obtained when benzoyl acetic acid is heated with soda-lime is
(A) COCH3 (B) COOH
(C) CH3 (D)
Ans. (A)
84. An aromatic compound ‘X’ (C9H8O3) turns blue litmus to red. It gives yellow precipitate with I2/NaOH and forms
Y(C8H6O4). Y forms three mononitro isomers. Identify X :
COCH3 COCH3 COCH3
COOH
(A) (B) (C) (D) None of these
COOH
COOH
Ans. (A)
COCH3
H OH
85. One mole of H OH was treated with NaOH/I2 and then acidified. The product after acidification has
NO2
COCH2I
isolated and then heated with 3 equivalents of NaOH to give a new ionic species. The ionic species formed will be:
COO COCH3 COO COO
(A) H O (B) H O (C) H O (D) H OH

H O H O H OH H O
NO2 NO2 NO2 NO2

COCH2I COO COO COO
Ans. (D) Kota, Rajasthan – 324005 Mob. : 9214233303
(i )Grignard reagent (excess)

86. Phenyl ester   'P ' , ‘P’ can be
(ii )H 
Ph Me Ph Ar Ph Me R R
(A) (B) (C) (D)
H OH Me Et R
OH OH OH
Ans. (D)
87. The end product of following reaction is :
O O
CH3MgBr 
PhMgBr H

(1)
 (2)
 
(3)
O
(A) -diketone (B) -Hydroxy acid (C) 1,2 - Diol (D) -Hydroxy ketone
Ans. (B)
(1)Mg  Hg conc.
88. 
(2)H 2O
 
H 2SO 4
 Major Product
O O
(A) (B)
O
O O
(C) (D)
Ans. (D)
Multiple Choice Questions
1. Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by :
(A) I2/NaOH (B) NaSO3H (C) NaCN / HCl (D) 2,4-DNP
Ans. (A,B)
2. An optically inactive alcohol (A) C6H12O is oxidized by MnO2 to produce optically inactive carbonyl compound
while reduction of (A) by H2/Ni produces optically active compound. Possible structure(s) of alcohol is/are
(A) Hex-2-ene-1-ol (B) Hex-3-ene-2-ol
(C) 2-Methyl pent -2-ene-1-ol (D) 3-Methyl pent-2-ene-1-ol
Ans. (C,D)
3. Correct option(s) regarding following reaction sequence is/are :
HgSO4 Ba(OH)2 NaOH 6 Ag

CH3 C CH P Q R+S T
HgSO2 I2
'X'
COOH
(A) T is homologue of ‘X’ (B) R is sodium salt of
COOH
(C) P can produce S with NaOl (D) R is sodium salt of
Ans. (A,B,C)
(i) Ph3P
4. (A) CH CH3
(ii) BuLi
(iii) (B)
In above reaction (A) & (B) will respectively be
(A) Cl & CH3CHO (B) CH3CH2Cl & O
Cl
(C) & HCHO (D) Cl & CH3CHO
CH3
Ans. (A,B)
5. Correct option regarding following reaction sequence.
HgSO4 Ba(OH)2 NaOH
CH3 –CCH P Q R+S
'X' H2SO4  I2
6 Ag
T
COOH
(A) T is homologue of ‘X’ (B) R is sodium salt of
COOH
(C) P can produce S with NaOI (D) R is sodium salt of
Ans. (A,B,C)
O O O COONa
P : CH3–C–CH3 Q : CH3–C=CH–C–CH3 R: S : CHI3 T : HCCH
6. Which of the following compounds(s) give a sweet smelling product having anesthetic use in presence of Cl2,
NaOH, .
O
(A) (B) CH3 – CH – CH3

O I
O O
(C) CH3 – C – OH (D) Ph – C – CH 3
Ans. (A,B,D)
O O O O
Cl
 
Cl2 +NaOH OH ONa OH ONa
Cl
CHCl3+
Cl2 CCl3 ONa

O O
O O
7. In which reaction haloform is obtained as one product :-

(A) Electrolysis of ethanolic aqueous solution of NaCl
(B) Isopropanol with bleaching powder
(C) Chlorination of methane in sun light
(D) Chloral is treated with NaOH
Ans. (A,B,C,D)
3 ( i ) Ph P
8. (A)  
 
(ii ) BuLi
(iii ) ( B)
In above reaction (A) and (B) will respectively be
(A) & CH3CHO (B) CH3CH2Cl &
(C) & HCHO (D) & CH3CHO
Ans. (A, B)
9. Which of the following form stable hemiketal
O O
|| ||
(A) Ph  C  Ph (B) HO  (CH 2 ) 3  C  CH 3
O O
|| ||
(C) CH 2 OH  C  (CHOH)3  CH 2  OH (D) HO  CH 2  ( CH 2 ) 4  C  CH 3
Ans. (B, C, D)
10. Which of the following is example of 1,4-addition reaction
O
|| ( i ) NaCN
(A) CH 2  CH  C  H  
( ii ) H 2O
O
|| LAH
(B) CH 2  CH  C  H 

H 2O / H
CH ONa / CH OH
(C) + CH2(COOMe)2 3 3

H
3O
CH CH  CN
(D) 2  

Base
Ans. (A, C, D)
11. Which of the following statements are correct about the following reaction ?
Cl LAH
(B)
LBAH
O (C)
Lithium tri-t-butoxyaluminium
hydride [Li(O-t-Bu) 3AlH]
(A) The produces (B) and (C), respectively, are : Me2CHCHO and Me2CHCH2OH.
(B) The produces (B) and (C), respectively, are : Me2CHCH2OH and Me2CHCHO.
(C) LBAH is more reactive reducing agent then LAH.
(D) LBAH is less reactive reducing agent then LAH.
Ans. (B, D)
12. Which of the following reactions would give propanal ?
(A) Ethyl proponate + DBAH (diisobutyl aluminium hydride). [(i-C4H9)2AlH)] at –70°C, followed by hydrolysis.
(B) Propyl propanoate + DIBAL-H/H2O
(C) Ethyl cyanide + DBAH
(D) Propanoyl chloride + LBAH
Ans. (A, B, C, D)
13. Which of the following reactions are correct?

O
LDA
(A) Me + MeCHO 
THF
 One crossed aldol products
O 
OH
(B) Me + MeCHO   Two crossed aldol products
Me
(C) 3 O 
Conc.H SO

 Phorone
2 4
Me
Me
Dry HCl
(D) 3 O   Mesitylene
Me
Ans. (A, B, C)
14. Which of the statements are correct about the internal or intramolecular Cannizzaro reaction given below ?
O OH
OH
2 1 –
Ph CHO Ph COO
(A) OH attacks at C– 1 of (CHO) group.
(B) OH attacks at C– 2 of (C = O) group.

(C) H– transfer takes place from C–1 to C–2.
(D) H ecxchanges from acid to alcohol ion.
Ans. (A, C, D)
15. Which of the following statements are correct about the reaction given below ?
O
HCN Sn  HCl HNO2

Traces of KOH
(B)  (C)  (D)
(A)
(A) In the formation of (D) from (C), ring expansion takes place.
(B) The product (D) is cyclopentanone.
(C) The product (D) is ,-unsaturated cyclopentanone
(D) Conversion of (B) to (C) can also be carried out with LAH.
Ans. (A, B, D)
16. Which of the following are Perkin reactions ?
NaOAc
(A) Me CHO + Ac2O
COOH
Me
O CHO
COONa
(B) Me CHO + O
O
COOH
Me
COOEt
(C) Me CHO + R3N
COOEt
COOH
Me
COOMe
NH3/EtOH
(D) CHO +
COOEt
COOH
Ans. (A, B)
17. Which of the following are correct reactions ?
NO2
O+ OH
(A) Me NO2 
Me
NO2
(B) O+ OH
Me NO2  Me
?
CH3COO NH4
COOEt
(C) O + NC
COOEt
CN
?
CH3COO NH4
COOEt
(D) O + NC
COOEt
CN
Ans. (A, C)
18. Which of the following statements are true about the benzoin reaction ?
aq.alc.
O2N CHO + Me CHO 
KCN

(A) (B)
(A) CN attack at the (C=O) group of (A)
(B) CN attack at (C=O) group of (B)

(C) The major product formed is
O2N Me
OH
(D) The major product formed is
OH
O 2N Me
O
Ans. (A, C)
19. Which of the following statements are correct about the following reaction ?
OH OH
H HNO2
 (C) 
OH NH2
(A) (B)
(A) In the formation of (C) from (A) or (B), expansion of ring takes place.
(B) In the formation of (C) from (A) or (B), contraction of ring takes place.
(C) Product (C) is CHO
CHO
(D) Product (C) is
Ans. (B, C)
Me O *

20.  (B)
Me Me
(A)
Which of the following statements are correct about the above reaction ?
(A) The reaction is called Claisen-Schmidt reaction.
(B) The reaction is called Claisen rearrangement reaction.
*
Me
(C) Product (B) is
Me
Me
O
*
Me
(D) Product (B) is
Me
Me
O
Ans. (B, C)
21. Which of the following are correct products ?

O
Me 
NaNO2 Ac2 O
(B)  (C)
 HCl at 0°C
Ph
The products given are :
O
CH N OH
(A)
Ph
O
Me
Ph
(B)
N
OH
O
C N
(C)
Ph
O
Me
(D)
N
Ans. (B, D)
Misc. Exercise
Subjective Type Questions
1. Predict the organic products :

CH2 CH2 CH2 NH2
O +
(i) H+/
(i) H /
(A) CH3 C CH3 + CH3 CH2 NH2 (B) (ii) H2/Pt
(ii) H2/Pt O
O
(i)Cl2 /NaOH/HOH
(C) C CH3  (ii)H

2. Identify A to E :
CH3 O
NaOH
(A) + (B)
Br2(leq)
(Structural isomer)
(i )
CH 2O/
(ii
3
M
)H
gB
(i) [SH 
r
SH
H
(ii) H2/Pt Conc. H2SO4/

(D) (E)
(C)
3. Complete reaction sequence :
(i) OH
(i) O3(leq) (i) OH
(I) (A) (B) (II) (ii) C 6H 5CHO Product
(ii) Zn/ H2O (ii) 
(iii) 
O
4. Complete the following reactions :

O OH O
CH 3 CH – CH 3
OH OH
(I) (X) + (Y) (II) (X)
CH3
OH
(i) OH
(III) [X]
(ii) 
(i) C 2H 5ONa
5. C6H5COOC2H5 + CH3COOC2H5 (ii) Acidification
D + D’
Ethyl benzoate
COOPh (i) PhONa
6. PhOOC F
(ii) Acidification
CH 2CH 2COOEt 
(i) C 2H 5ONa H 3O
7. C 2H 5–N G H (Piperidone derivative)
CH 2 CH2COOEt
(ii) Acidification 
(i) (CH 3CH 2CO) 2 O/CH 3–CH 2–COONa,

8. H3 C CHO + A
(ii) H /H 2O, 
O
O C – Me
Et2NH
Ph – C – H + CH2 D
9. 
C – OEt
O
O
10. nC5H 11NH 2
Ph – C – H + CH3 – NO 2 E

CN O
NaOEt
11. CH 2 + Ph – C – H G

NO 2
O2 N Me
NO 2 + Ph – NO OH/ H
12.
O2N
O COOR
EtONa
CH – CH3 + CH2 +
?
(ii) H3O ,
13. COOR
O
(i) Zn
(ii) PhCHO
14. OEt  B
(iii) H 3O, 
Br
15. (i) Zn (i) 

+ BrCH2COOEt  D E
(ii) H3 O (ii) Se/
-Tetralone
Br
(i) Zn/Et2O (i) 
16. EtO – C – CH – CH2CH2CH2 – CH2 – CHO  F G
(ii) H3O (ii) Se/
O
O O
OH
17. CH3 C – C – C6H5
OHO
Fenton (i) OH
18. C6H5 – C – CH – C6H5 A  B.
reagent (ii) HOH / H
O
19. (i) NaOH
(ii) H3O
O
Li Cul CH3CH2CH2CH2CH2I
20. CH3 – I (A) (B) (C)
Et2O  
Li Cul CH3CH2CH2CH2CH2Br
CH3CH2CH2CH2Br (D) (E) (F)
Et2O  
CH3 – CH – CH3
Cl
(C)
Li CuBr
21. CH3 – CH2 – Br (A) (B)
 O
(i)
(D)
(ii) H

H
22. (CH3)2 CuLi + CH3 – CH – CH 2 (A) (B)
O
23. How many of the following compounds will give iodoform test positive ?
O OH O
(a) OH (b) CH3 C CH3 (c) CH3 CH Ph (d) C
OH O O
(e) (f) (g) CH3 C OH (h) CH3 C COOH
OH
O
O O O
(i) CH3 C OMe (j) (k) Et C CH2 C Et
O
(l) CH3 – CH2 – CH2 – OH (m) Ph – CH2 – OH
(i) NaOH 
24. Ph C CH O + A Products
(ii) H
O
What is the number of possible products ?

25. Number of compounds can be oxidised by Tollen’s reagent.
O
O
CH O O
CH
(i) (ii) H C OH (iii) (iv)
O
O
O OH OH O CH3
(v) (vi) CH2 C (vii) CH3 C (viii)
O CH3 CH2 OH
OH CH3 CH3
O
26. Number of reagents which converts CH3–CHO into carboxylic acid or its salt :
(1) Cu/573 K (2) Fehling’s reagent (3) Na/Liq. NH3 (4) Tollen’s reagent (5) NaOH/I2
+ +
(6) Bayer’s reagent (7) H /KMnO4/ (8) H2/Pd (9) H /K2Cr2O7/ (10) OH–/
27. The compound among following which can give 2, 4-DNP test (2, 4-dinitrophenylhydrazine test)
O
(1) (2) (3) (4)
O NH
NH2
O
(5) (6) (7) H (8) HCHO
O
O
O H
(9) (10)
O
28. Consider all possible isomeric ketones including stereoisomers of MW = 100. All these isomer are independently
reacted with NaBH4 (Note : stereoisomers are also reacted separately). The total number of ketones that give a
racemic product(s) is/are :
29. 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). Maximum number of CH3MgBr consumed by A, B, C, D are
Comprehension :
Paragraph -1 (30-32)
An alkene (A) C16H16 on ozonolysis gives only product (B) C8H8O. (B) can also be obtained by hydrolysis of the
product obtained by reaction between cyano benzene and CH3MgBr. (A) can show geometrical isomerism can it
can decolourise Br2 water. (B) on treatment with SeO2 produces (C).
30. Which is not correct about ( A ) ?
(A) A is optically in active
(B) On catalytic hydrogenation ‘trans’ from of A produces racemic mixture
(C) A can be prepared by Witting reaction on acetophenone with Ph3P = C(CH3)Ph.
(D) On treatment with per acid followed by hydrolysis ‘trans’from of A produces racemic mixture
31. Which is not correct about B ?
(A) It gives iodoform test
(B) On treatment with LiAlH4, H2O it produces a compound which also responds to iodoform test.
(C) It gives Tollen’s test
(D) On treatment with NH2NH2 followed by alc. KOH at high temperature, it produces ethyl benzene.
32 Which is not correct about C ?
(A) On treatment with NaBH4 it will produce a diol.
(B) On treatment with OH– (conc.) followed by acidification racemic mixture of a carboxylic acis is obtained.
(C) It gives Tollen’s test.
(D) It can take part in aldol condensation.
Paragraph - 2 (33-34)
A(Hydrocarbon) (C = 88.24%) [Molecular weight of A = 68]

(i) Na
A (ii) n-propyl bromide B(C8H14)
2+
Hg
A C5H6O (C)
dil. H2SO4
KMnO4
A + Carboxylic acid + Gas
H
Q.33 ‘A’ can be :

(A) H3C–H2C–CC–CH3 (B) CH3–CH2–CH2–CC–H
CH3
(C) CH3 CH C CH (D)
CH 3
34. Correct statement reagarding C is.

(A) C reacts with fehling solution to give red ppt. (B) C gives +ve iodoform test
(C) C give -ve 2, 4 D.N.P test (D) C is aldehyde
Paragraph - 3 (35-36)
In given reaction sequence
(i) O3
(A) (B) + (C)
C10H20 (ii) Zn/H2O Racemic mixture
Optically of carbonyl compound
Inactive alkene
H2N OH
Br2
in CCl4
Oxime(s)
(D) + (E)
Mixture of two different
meso compounds
35. Alkene A is :
H H
(A) (B)
H
H
H H
(C) (D)
H
H
36. How many total oxime(s) is/are obtained :

(A) 1 (B) 2
(C) 3 (D) 4
Paragraph - 3 (37 to 39)
Observe the following reactions.
H2SO4 / 
H2SO4 (i)MeMgBr (1eq.) LiAlH4 (80 )
X (1)
 Y 
(ii)H (2)
 (Z)  (3)
(W) 
(4)  H2O

C6H12O2 Me O Me
(M.F.)
37. The compound ‘X’ is
HO O
(A) COOH (B) COOH
Me Me
O COOH HO COOH
(C) (D)
Me Me
38. Compound ‘Y’ is
(A) (B)
Me O O Me O O
O COOH
(C) Me COOH (D)

Me
39. The correct statement about ‘Z’ and ‘W’ is

(A) Both give positive Tollen’s test (B) Both give positive iodoform test
(C) Both give positive test with 2, 4-DNP (D) W on CrO3 / H oxidation gives Z.
Match the Column
40. Match the reactions in Column -I with appropriate types of step/reactive intermediate involved in these reactions as
given in Column II
Column - I Column - II
H3 C O
O aq NaOH
(A) (P) Nucleophilic substitution
O
O
CH3MgI CH3
CH2CH2CH2Cl
(B) (Q) Electrophilic substitution
18 O
O
18 H2 SO4
(C) CH2CH2 CH2OH (R) Dehydration
CH2 CH2CH2C(CH3 )2 H2SO4
OH
(D) (S) Nucleophilic addition
H3C CH3
(T) Carbanion
41. Match the column :
(A) HCHO + NaOD (conc.) (P) DCOO– + CDH2OH
(B) DCHO + NaOH (conc.) (Q) DCOO– + CD2OH
(C) DCDO + NaOH (conc.) (R) DCOO– + CDH2OD
(D) DCHO + NaOD (conc.) (S) HCOO– + CH3OD
42. Column - I Column - II
(Reactions) (Intermediate formed or type of reaction)
O O
OH–
(1)  (P) Product obtained as racemic mixture
O
+ H
(2) OH OH O O (Q) Substitution reaction
+ conc. + conc.
HNO3 H2SO4
(3) (R) Nu– Addition takes place during reaction.
NO2
OH
O (1) LaH
(4) (S) Carbocation intermediate
(2) H2O
(T) Carbanion intermediate
43. Match the columnn

COOEt
(1)EtONa
(A) Ph CHO+ CH2 
(2)H O /  (P) Perkin’s reaction
3
COOEt
(1) Zn
(B) Ph CHO+ CH2 COOCH3 
(2)H3O /  (Q) Reformatsky reaction
Br
(1)CH 3COONa/ 
(C) Ph–CHO + CH3COOCOCH3 
(2)H 3O  / 
 (R) Product is a carboxylic acid with aromatic ring within
the same molecule.
O O
(D) Ph C C Ph +NaOH 
(2)H 

(S) Double bond equivalent of the product formed is less
than or equal to 8.
(T) The major product cannot show optical isomerism.

Carbonyl Compounds

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Carbonyl Compounds

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FINAL TOUCH

Single Choice Questions

Identify product (A) & (B) from the given product P, Q, R :

Product (D) will be

(1) (2) (3)

–ive Tollens test

Product (A) and (B) is differentiated by :

HCN LiAlH4 NaNO2

End product (C) in above reaction is :-

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

(A) (B) OH (C) HCHO (D) Both (A) and (C)

17. Consider the following sequence of reactions.

The ketone (A) is

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

H3C CH3 H3C CH3

Product (Q) will be :

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

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

25. C N + CH3MgBr 

Product (A) and (C) is :

(A) and (B) is differentiated by :

CH2 CH2 CO2H

(A) CH3 – CH = CH – CH2 (B)

29. End products of the following sequence of reactions are :

(A) yellow ppt. of CHI3, (B) yellow ppt. of CHI3,

NH 2OH H 2SO4 H3O CHCl3 

Molecular weight of compound (A) is :

HO– Compound (C) is :

34. Ph – CH = CHCHO + CH3CH = CHCHO

(A) Ph –(CH = CH)2 – CHO (B) Ph – (CH = CH)3 – CHO

37. The reaction,

Number of intramolecular aldol condensation product is :

(A) CH3(CH = CH)3CHO (B) CH3CH2CH2(CH = CH)2CHO

(A) + CH3OH (B) + HCO2

(C) + HCOOH (D) + CH3OH

47. In the given reaction:

[X] will be:

C6H5CHO + CH3 – CHO OH Product

49. In the given reaction

(X) and (Y) will respectively be :

50. Acetophenone can be obtained by the distillation of :

(A) (C6H5COO)2Ca (B) (CH3COO)2Ca

(C) (C6H5COO)2Ca and (CH3COO)2Ca (D) (C6H5COO)2Ca and (HCOO)2Ca

51. The given reaction :

(A) Perkin reaction (B) Knoevenagel reaction

O2N CHO + (C6H5 CH2CO)2O

(A) C6H5 CH CH COOH (B) NO2 CH CH COOH

(C) C 6H 5 CH C COOH (D) NO2 CH C COOH

53. In the given reaction :

NaBH4 (X) (i) BH3 (Y)

(X) and (Y) are :

(A) CH2 OH and HOCH 2 O

(B) CH 3 O and HOCH2 O

(C) CH 2 OH and CH3 OH

(D) CH2 OH and CH3 O

Identify relationship between A & B Products ?

56. In the reaction sequence

The products (B) is :

can be effected by using the reagent

Organic product P & Q are respectively -

(A) 0 (B) 4 (C) 8 (D) 2

63. Consider the following reaction sequence.

The products (A) and (B) are, respectively.

64. Consider the following sequence of reactions.