1. 1
CHEMISTRY
MULTIPLE CHOICE QUESTIONS (SINGLE OPTION CORRECT)
31. In which reaction, product formation occurs by Saytzeff rule?
(1) ONa
CH3
Br
CH3



,  (2)
H2C
CH3
C
H3
OH
CH3
2 4
conc. H SO


(3)
CH3
CH3
Ph
Br
aq. KOH/ 

 (4)
Cl
F3C
Cl CH3
Cl / h
2 


Select the correct alternative from the codes given below:
Codes:
(A) 1, 2 and 3 (B) 2 and 3
(C) 1, 2 and 4 (D) 2, 3 and 4
32.
CH3 CH3
The best way of bringing about the above conversion is by using
(A) NBS; alcoholic KOH (B) HBr; (CH3)3COK – (CH3)3COH
(C) HBr-peroxide; CH3CH2OK – CH3CH2OH (D) HBr-peroxide; (CH3)3COK – (CH3)3COH
33. 2 H
X


X will be
(A)
(B)
(C) (D)

2. 2
34.
P is
(A)
CHO
CHO
(B)
COO
CH2OH
(C)
COO
COO
(D)
CH2OH
CH2OH
35. Consider the following reactions:


 


3 4
4 (CH COO) Pb
dil. KMnO
cold
X Y
The product (Y) is
(A)
OH
OH
(B)
CH2COOH
CH2COOH
(C)
O
O
(D)
OH
OH
36. Which of the following pair is correctly matched?
(A) Saytzeff rule, least substituted alkene (B) Hofmann rule, most substituted alkene
(C) E1CB reaction, Hofmann elimination (D) E1 reaction, Hofmann elimination
37. 2
2
Hg /H
3 H O
Ph C C CH (W)
(Major)
 
   

(W) is
(A)
O
Ph
CH3
(B)
Ph
CH3
O
(C)
OH
Ph
CH3
(D)
Ph
CH3
OH

3. 3
38. In the reaction,
CHO
CH3
O
conc. NaOH
H ,
The product P is-




(A)
COONa
CH3
OH
(B)
CH2OH
COONa
(C)
CH2
CH2 OH
OH
(D)
COOH
COOH
39. The correct order of increasing rate of hydrolysis of the following compound is
CH3COOEt C2H5COOEt iso-pr-COOEt
(I) (II) (III)
(A) I < II < III (B) III < II < I
(C) I < III < II (D) III < I < II
40. The order of reactivity of given halides towards SN2 reaction is
(A) PhCH2Cl > PhCHClCH3 > PhCCl(CH3)2
(B) PhCH2Cl < PhCHCl(CH3) < PhCCl(CH3)2
(C) PhCHCl(CH3) > PhCH2Cl > PhCCl(CH3)2
(D) PhCHCl(CH3) > PhCCl(CH3)2 > PhCH2Cl
41. Which chloro derivatives of benzene among the following undergoes hydrolysis most readily with
aqueous NaOH to furnish the corresponding hydroxy derivative?
(A) Cl
O2N
NO2
NO2
(B) Cl
O2N
(C) Cl
N
C
H3
C
H3
(D) Cl
42. The order of reactivity of the following alcohols towards conc. HCl is
F
CH3
OH
I
F
HO
CH3
II
OH
CH3
H3C
III
Ph OH
IV
(a) I > II > III > IV (B) I > III > II > IV

4. 4
(C) IV > III > II > I (D) IV > III > I > II
43. Which of the following will be oxidized by HIO4?
(1)
R
O O
R
(2)
R
O OH
R
(3)
R
OH
R
OH
(4)
R
O
H
R
OH
Select the correct answer using the codes below:
(A) 1, 2 and 3 (B) 1, 3 and 4
(C) 1, 2 and 4 (D) 2, 3 and 4
44.
CH3
CH3
OH 2 4
2
Br / CCl
H
4 8 2
H O
(F) C H Br



 

How many structures of ‘F’ are possible?
(A) 2 (B) 5
(C) 6 (D) 3
45. In the given conversion, identify the reagents X, Y and Z.
CH3
(i) A
(ii) B
(iii) C


CH3
O
(A) X : H2O2 in aqueous NaOH, Y : PCC/CH2Cl2, Z : B2H6/THF
(B) X : B2H6/THF, Y : Br2/CH2Cl2, Z : PCC/CH2Cl2
(C) X : B2H6/THF, Y : H2O2/OH–
, Z : PCC/CH2Cl2
(D) X : Br2/CH2Cl2, Y : B2H6/THF, Z : H2O2/OH–
46. Glycerol on oxidation with Fenton’s reagent produces
(A) glyceraldehyde (B) dihydroxyacetone
(C) tartaric acid (D) glyceraldehyde and dihydroxyacetone
47.
O
CH3



3
(i) NaH/ dry ether
(ii) CH I
(Y)
(major)


3
(i) LDA
(ii) CH I
(X)
(major)
Hence, X and Y are respectively
(A)
O
H3C CH3
and
O
CH3
CH3
(B)
O
H3C CH3
O
CH3
CH3
and
(C)
O
CH3
H3C
O
CH3
CH3
and
(D)
O
CH3
CH3
O
CH3
CH3
and

5. 5
48.
O
H3C CH3
O


2 3
aqueous K CO
Major product (X)
Product (X) in the above reaction is
(A)
OH
CH3
(B)
HO
O
CH3
(C)
CH3
OH
O
(D)
HO
CH3
O
49. 3
3
CHCl RLi
2 Ph P
Et C O X

 

(A)
Cl
Cl
Et
Et
(B)
Et
Cl
Et
Cl
(C)
O
Et
Et
R
Cl
Cl
(D) None of the above
50.
CHO
OCH3
CHO
NO2


 
OH
X Y
X and Y are respectively
(A)
COO
OCH3
CH2OH
NO2
(B)
CH2OH
OCH3
COO
NO2

6. 6
(C)
COOH
OCH3
CH2O
NO2
(D)
COOH
NO2
CH2O
OCH3
51. A carbonyl compound C5H10O gives Cannizzaro’s reaction. What will be its Tischenko reaction’s
product?
(A)
C
H3
C
H3
CH3
O
O
C
H3
CH3
CH3
(B) COO
C
H3
CH3
CH3
(C) C
H3
CH3
CH3
OH
(D) None of the above
52. C
H3
O
COOC2H5



 

3 2
(i) NaH/ THF (i) dil. KOH
(ii) CH COCl (ii) H O/H ,
(X) (Y)
The product (B) in the above sequence of reaction is
(A)
C
H3
O
COOC2H5
COCH3
(B) C
H3
O
COOH
COCH3
(C)
C
H3
O
CH3
O
(D)
C
H3
O
COOH
53. An organic compound C8H9NO is found to be insoluble in dilute acid and base. On treatment with
KMnO4/H2SO4, the compound formed is devoid of nitrogen and is soluble in NaHCO3 and on nitration
produces mono nitrosubstituted product, the organic compound C8H9NO is
(A)
CH3
O NH2
(B)
COOH
O NH2
(C)
O H
NH2
(D)
NH2
O CH3

7. 7
54. Br – CH2 – CH2 – Br can be converted into HOOC – CH2 – CH2 – COOH by using
(A) NaCl, H2O + H2SO4 (B) NaCN, H2O + H2SO4
(C) H2O + H2SO4, KMnO4 (D) KCl, H2O + H2SO4
55. Which compound will lose its chirality when it is heated?
(A)
COOH
H3C
OH
(B)
H3C
OH
COOH
(C)
COOH
H3C
COOH
(D)
O
COOH
CH3
56.


 

3 2 2
CH I Ag O/H O
(Hydrocarbon)
A B
N
C2H5
C
H3
Ph
CH3
Hydrocarbon ‘B’ is,
(A) CH4 (B) 2 2
CH CH

(C) 2 3
CH CH CH
  (D) 2
Ph CH CH
 
57. C
H3 N
O
Ph
H





H /DMSO
Major product;
Which of the following is major product?
(A)
H2C NH
OH
Ph
(B)
C
H3 H
O
Ph NH2
(C)
NH2
C
H3 O
(D)
C
H3 N
OH
Ph

8. 8
58. tBuO
?



N
Me
I
H
(A)
N
H
(B)
N
Me
(C)
N
(D) All
59.
 
3
H O
KCN
2 4 2
R
C H Cl (X) (Y) (Z)



 
 

The compound Z has the characteristic(s)
(A) It is succinic anhydride if (R) is vic dihalide
(B) It is propionic acid if (R) is vic dihalide
(C) It is succinic anhydride if (R) is gem dihalide
(D) It is propionic acid if (R) is vic dihalide
60.

 

3
2
(i) O NaOH
(ii) H O/ Zn
(X) (Y)
The end product (Y) in the above sequence of reaction is
(A) O (B) OH
(C)
O
O
H
(D)
O O

9. 9
ANSWERS
31. B
32. D
33. D
34. B
35. C
36. C
37. A
38. A
39. A
40. A
41. A
42. C
43. C
44. D
45. C
46. D
47. B
48. B
49. A
50. A
51. A
52. C
53. A
54. B
55. B
56. B
57. C
58. B
59. A
60. C
HINTS & SOLUTIONS
31. (1) proceeds through E2 path while (2) and (3) proceeds through E1 path and (4) proceeds through
E1CB path.
Hence, only 2 and 3 takes place through Saytzeff rule.
33. H

H
H



34. (i), (ii) ozonolysis
(iii) Intramolecular Cannizzaro reaction.
36. E1CB reaction favours Hofmann elimination, bad leaving group, and a very strong base.

10. 10
37.
2
2
2
H O
Hg
3 3 Hg
Ph C C CH Ph C C CH




   
     Ph
O
H
CH3
tautomerise Ph
O
CH3
more stable
(incipient carbocation)
Hg
2
38. This is intramolecular Cannizzaro reaction.
39. I < II < III, due to stearic hindrance.
Hence, (A) is the correct answer.
40. Less hindered the substrate, more reactive it will be towards SN2 reaction.
41. The nucleophilic substitution in aryl halide is assisted by the presence of electron withdrawing group
at ortho and para position. Here, the number of electron withdrawing groups are more, so hydrolysis would
be easier.
43.
R
O O
R
(1)
4
HIO


R
O
OH O
H
O
R
R
O OH
R
(2)
4
HIO


R
O
OH
O R
4
HIO
(4) R CHOH CHOH R R CH O R CH O
   
     
44.
CH3
CH3
OH
H

CH3
CH3
OH2
2
H O


 C
H3
CH3
H


 C
H2
CH3
C
H3
CH3
(cis and trans)
Hence, (D).
46. CHOH
CHO
CH2OH
CHOH
CH2OH
CH2OH
4
2 2
FeSO
H O

 CO
CH2OH
CH2OH
Glyceraldehyde Dihydroxyacetone
47. Small bases like NaH abstract H+
ion from highly substituted   carbon atom while bulky bases
like LDA abstracts H+
from less substituted   carbon atom.
Hence, (B).
48.
O
H3C CH3
O
2 3
K CO
(Intramolecular aldol
condensation between a and b)


a
b
OH
H3C
O or
HO
O
CH3
Product (A)

11. 11
Hence, (B).
49. Wittig reaction
3 3 2 3
CHCl Ph P RLi CCl PPh RH
(ylide)
  
  
50. In cannizzaro reaction, the hydride transfer is the rate determining step.
52. C
H3
O
COOC2H5
NaH/THF

 C
H3
O
COOC2H5
3
CH COCl

 C
H3
O
COCH3
COOC2H5
(A)
(i) dil. KOH (ii) H
+
C
H3 CH
O
COCH3
COOH
( , keto acid)
  


2
CO



C
H3
O
CH3
O
(B)
53.
CH3
O NH2
4
2 4
KMnO
H SO


COOH
COOH
nitration


COOH
COOH
NO2
54.
Br
Br 2NaCN
 

CN
NC 2 2 4
hydrolysis
H O H SO



COOH
HOOC

12. 12
56. 3
CH I


N
Ph
N
+
Ph
I
N
+
Ph
OH
Ag2O/H2O



N
H2C CH2
57.
C
H3
N
O
Ph
H
H

C
H3
N
+
O
H
H
Ph C
H3
C
O 2
Ph NH
 
NH2
C
H3 O
58. tBuO Li



NH
Me
I
H N Me N Me H
N
Me
59. H
Cl
H H
Cl
H KCN
 
 NC
CN 3
H O

 HOOC
COOH
2
H O




O
O
O
(R)
Succinic anhydride
3
H O
KCN
3 2 3 2 3 2 3 2
decarboxylation
(R) H C CHCl H C CH(CN) H C CH(COOH) CH CH COOH


 
  
  

60. 3
2
(i) O
(ii) H O/ Zn


O
(A)
2 NaOH
(Aldol condensation)


O
O
H