264

5A
ALKYL HALIDES

Substitution Reactions (SN , SN , SN ) 1 2 i

Level - 1
1. Which of the following is not expected to be intermediate of the following reaction ?
OH
I
H2O

+
+ OH2
+
+
(a) (b) (c) (d)

CH3
Br H
2. + NaI ¾ ¾¾¾® product; S N 2 product of the reaction is :
Acetone
H CH3

CH2 – CH3

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CH3 CH3 CH3 CH3
I H H I I CH3 I H
(a) (b) (c) (d)
H CH3 H CH3 H CH3 CH3 H
CH2 – CH3 CH2 – CH3 CH2 – CH3 CH2 – CH3
3. Rate of S N 2 will be negligible in :
Br Br Br Br

(a) (b) (c) (d)

4. What is the major product obtained in the following reaction ?

CH2–Br
NH 3
¾ ¾¾® product
EtOH
Br
CH2–NH2 CH2–Br CH2–NH2 CH2–NH2
(a) (b) (c) (d)
Br NH2 NH2

CH 3
|
5. Cl - CH 2 - C - CH 2 - CH 2 – Cl + I - ¾ ¾¾® product; Major product of this reaction is:
| DMF
CH 3
CH 3 CH 3
| |
(a) I - CH 2 - C - CH 2 - CH 2 – Cl (b) Cl - CH 2 - C - CH 2 - CH 2 - I
| |
CH 3 CH 3
CH 3 CH 3
| |
(c) H 2 C = C - CH 2 - CH 2 = Cl (d) Cl - CH 2 - C - CH 2 = CH 2
|
CH 3
6. Which of the following expressions is representative of the rate law for a S N 2 reaction ?
(a) Rate = k [electrophile] (b) Rate = k [electrophile] [nucleophile]
(c) Rate = k [nucleophile] 2 (d) Rate = k[electrophile]2

7. H F+ NaI (1 mole) ¾ Acetone

¾¾¾® ( A) ; Major product of this reaction is :
Br H (major)

(a) H F (b) I F (c) H I (d) H H

I H H H Br H Br I

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8. Which of the following alkyl halide undergo rearrangement in S N1 reaction ?
CH 3 Cl
| I
(a) CH 3 – C – CH – CH 3 (b) (c) (d) All of these
| | CH3
CH 3 I
9. Arrange the following three chlorides in decreasing order towards S N1 reactivity.
(1) Cl (2) (3)
Cl Cl
(a) 1 > 2 > 3 (b) 2 > 3 > 1
(c) 2 > 1 > 3 (d) 3 > 2 > 1
10. Which compound undergoes nucleophilic substitution with NaCN at the fastest rate ?
Br
(a) Br (b) (c) Br (d) Br

11. Rank the following in order of decreasing rate of solvolysis with aqueous ethanol (fastest ®
slowest)
CH 3 CH3 Br
| |
H 2 C = C — Br Br CH 3 - CH CH 2 CH(CH 3 ) 2
(1) (2) (3)
(a) 2 > 1 > 3 (b) 1 > 2 > 3
(c) 2 > 3 > 1 (4) 1 > 3 > 2
12. The reaction of 4-bromobenzyl chloride with sodium cyanide in ethanol leads to the
formation of :
(a) 4-bromobenzyl cyanide (b) 4-cyanobenzyl chloride
(c) 4-cyanobenzyl cyanide (d) 4-bromo-2-cyanobenzyl chloride
13. Which of the following reactant will not favour nucleophilic substitution reaction ?

(a) (b) Ph - Br
Br
CH 3
|
(c) CH 3 - C - CH 2 - Br (d) All the above
|
CH 3
Br OH

OH –
14.

H H
(I) (II)

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Conversion of I to II :
(a) takes place by S N1 (b) takes place by S N 2
(c) takes place both by S N1 and S N 2 (d) does not take place
15. Which is the correct reaction coordinate diagram for the following solvolysis reaction ?
CH3 CH3 OH
H2O
Br OH CH3

(a) (b)
Reaction Coordinate
Reaction Coordinate

(c) (d)
Reaction Coordinate
Reaction Coordinate

14C labelled
OTs
RCO H
16. ¾ ¾¾
2
¾® product; Product of this reaction is :
no label
OCOR OCOR
(a) (b)

(c) both (a) and (b) (d) None of these

I
CH3
NBS CH 3SNa
17. ¾ ¾¾® (A) ¾ ¾¾¾ ® (B) , Product (B) is :

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I I
CH2–S–CH3 S–CH3
(a) (b)

S–CH3
CH2–Br
(c) (d) None of these

18. Which of the following represents the correct graph for S N 2 reaction ?

log (rate)

(a)
CH3 – Br CH3 – CH2– Br CH3 – CH– Br CH
| |
CH3 CH3 – C – Br
|
CH3

log( rate)
(b)

CH3 – Br Et – Br i – Pr – Br t – Bu – Br

log (rate)

(c)

CH3 – Br Et – Br i – Pr – Br t – Bu – Br
(isopropyl)

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log (rate)
(d)

CH3 – Br Et – Br i – Pr – Br t – Bu – Br
19. Which of the following graph represents correct graph for S N1 reaction :

log (rate)

(a)
CH3 – Br CH3 – CH3– Br CH3 – CH– Br CH3
| |
CH3 CH3 – C – Br
|
CH3

log (rate)
(b)

CH3 – Br Et – Br i – Pr – Br t – Bu – Br

log (rate)

(c)

CH3 – Br Et – Br i – Pr – Br t – Bu – Br

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log (rate)
(d)

CH3 – Br Et – Br i – Pr – Br t – Bu – Br

20. Which of the following is most reactive toward S N 2 reaction ?

Cl Cl Cl Cl

(a) (b) (c) (d)

CH3 Cl NO2
21. Among the given pairs, in which pair first compound reacts faster than second compound in
S N1 reaction ?
(a) CH 3 - CH 2 - CH 2 - CH 2 - Br or CH 3 - CH 2 - CH - CH 3
|
Br
CH 3 CH 3
| |
(b) CH 3 - C - CH 2 - CH 2 or CH 3 - CH - CH - CH 3
| |
Br Br

Br Br

(c) or

CH 3 CH 3
| |
(d) CH 3 - C - CH 3 or CH 3 - C - CH 3
| |
Br I
22. What is the major product of the following reaction ?
HBr
H 2 C = CH - CH 2 - OH ¾excess
¾¾® Product
Br
|
(a) CH 3 - CH - CH 2 - Br (b) H 2 C = CH - CH 2 - Br
Br OH
| |
(c) CH 3 - CH - CH 2 - OH (d) CH 3 - CH - CH 2 - OH

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23. S N1 and S N 2 products are same with (excluding stereoisomer) :
Cl

(a) (b)
Cl

(c) (d) Ph - CH - CH - CH 3
| |
CH 3 Cl
Cl
24. Consider the nucleophilic attacks given below. Select in each pair that shows the greater S N 2
reaction rate.
O
Br + ¯CN O CH3+ ¯CN
(A) or
(I) (II)

(B) H 3 C - Br + - SH or H 3 C - Br + CH 3 SH
(III) (IV)

(C) Br + Cl - or Br + I - in DMSO

(V) (VI)

(D) Br + Cl - or Br + I - in methanol

(VII) (VIII)
A B C D A B C D
(a) (I) ; (IV) ; (VI) ; (VIII) (b) (II) ; (III) ; (V) ; (VIII)
(c) (I) ; (III) ; (V) ; (VIII) (d) (I) ; (III) ; (V) ; (VII)
25. Which of the two stereoisomers of 4-t-butylcyclohexyl iodide ( 127 I - ) will undergo S N 2
128 -
substitution with I faster, and why ?
H I127
H H
H
I127
H
(A) (B) H
(a) A will react faster because it is the more stable of the two isomers
(b) A will react faster because it will yield a more stable product, and the transition state for
both reactions is of the same energy
(c) A will react faster because the approach of 128 I - can depart unhindered.

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(d) B will react faster because it is less stable than A, and the transition state for both
reactions is of the same energy
26. (Z )-2-Butene reacts with Br 2 H 2 O. The resulting bromohydrin when treated with
methoxide in methanol undergoes an intramolecular S N 2 reaction. Taking into
consideration the stereochemical consequences of the reaction mechanism involved,
choose the final product(s) of these transformations.
O O O
(I) H CH3 (II) H3C H (III) H H
H3C H H CH3 H3C CH3
(a) (I) only (b) (II) only
(c) (III) only (d) Equal amounts of (I) and (II)
27. Rank the following species in order of decreasing nucleophilicity in a polar protic solvent
(most ® least nucleophilic) :
O
||
CH 3 CH 2 CH 2 O - CH 3 CH 2 CH 2 S - CH 3 CH 2 C - O –
(1 ) ( 2) ( 3)
(a) 3 > 1 > 2 (b) 2 > 3 > 1 (c) 1 > 3 > 2 (d) 2 > 1 > 3
28. Identify products of the given reactions :
OTs
CH CO Na
Reaction-1 ¾ ¾¾¾
3 2
¾® Product
CH 3CO 2H
NMe2
OTs
CH CO Na
Reaction-2 ¾ ¾¾¾
3 2
¾® Product
CH 3CO 2H
NMe2
O CH3 O CH3
(a) O ; + enantiomer
O
NMe2 NMe2
O CH3 O CH3
(b) O + enantiomer ; O
NMe2 NMe2
O CH3
(c) O single product is obtained in both the reactions
NMe2
O CH3
(d) O single product obtained in both the reactions
NMe2

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A
B
log(rate)

29.

CH3–X Me–CH2–X Me2CH–X Me3CH–X

Which of the following is true about given graphs A and B ?

(a) A ® S N1 B ® S N 2 (b) A ® S N 2 , B ® S N1
(c) A & B ® E 1 (d) A & B ® E 2
30. In each of the following groups, which is the strongest (best) nucleophile ?
(I) (1) H 3 C - O - (2) O¯ (3) H 3 C - S - in CH3OH
(II) (1) OH - (2) H 2 O (3) NH -2 in DMF
O¯
(III) (1) (2) O¯ (3) CH 3 O - in DMSO
(a) I,3 ; II,3 ; III,2 (b) I,2 ; II,1 ; III,3
(c) I,1; II,2 ; III,1 (d) I,3 ; II,1 ; III,3
O
NaNH
31. S – (CH2)4 – CH2 – Cl ¾ dimethoxy
¾¾¾¾¾ 2
¾® ( A) ; Product ( A) is :
ethane
(Major)
O
O O
||
(a) S - (CH 2 ) 3 - CH = CH 2 (b) S
||
O O
O
||
(c) S - (CH 2 ) 4 - CH 2 - NH 2 (d) None of these
||
O
32. Which of the following reaction is an elimination reaction ?
H
H
H2SO4 Br KI
(a) OH ¾¾¾® +H (b) ¾¾® + IBr + KBr
H
Br
H H
NaOCH3
(c) Br ¾¾¾® OCH3 (d) both (a) and (b)

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CH 3ONa
33. ¾ ¾¾¾¾
¾® Product
CH 3OH(S 1 )
O CH2 – Cl N

Which of the following products can be obtained from above reaction ?

OCH3
(a) (b) (c) (d) All of these
O CH2 – OCH3 O
CH3O O CH3
34. What is the principal product of the following reaction ?
CH3
H Br
H H + NaN 3 ¾® Product
H Cl
CH3
CH3 CH3 CH3 CH3
H N3 N3 H N3 H H N3
(a) H H (b) H H (c) H H (d) H H
H Cl Cl H H Cl Cl H
CH3 CH3 CH3 CH3
35. What would be the effect of increasing solvent polarity on the rate of each of the following
reactions ? (Nu = neutral nucleophile)
Å
(A) Nu + R - L ¾® Nu - R + L-
(a) increases (b) decreases (c) constant (d) can not be predicted
(B) R - LÅ ¾® R Å + : L
(a) increases (b) decreases (c) constant (d) cannot predict
36. Which of the following is most reactive toward S N 2 reaction ?

(a) CH 2 = CH - CH 2 - Cl (b) Ph - CH 2 - Cl

(c) Me – O Cl (d) Ph - C - CH 2 - Cl
||
O
37. 4-chloro-1-butanol + NaOH ¾® ( B )
Product ( B ) of the above reaction is :
CH3
CH2 – CH3
(a) (b) (c) O (d)
O O O

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38. In the given pairs of alkyl-halide, in which pair the first compound is more reactive than
second compound toward S N 2 reaction ?
(a) (CH 3 ) 2 CHBr or CH 3 - CH 2 - CH 2 - Br
(b) CH 3 - CH 2 - CH 2 - Br or CH 3 - CH 2 - CH 2 - I
(c) Ph - Br or CH 3 - CH 2 - CH 2 - Br
(d) CH 2 = CH - CH 2 - Cl or H 2 C = CH - Cl
39. In the given pair of reaction in which pair the second reaction is more reactive than first
toward S N 2 reaction ?
(a) CH 3 - CH 2 - Cl + CH 3 - CH 2 - O – ¾® Et - O - Et (or)
CH 2 - CH 2 - Cl + CH 3 - CH 2 - OH ¾® Et - O - Et
(b) CH 3 - CH 2 - Cl + EtO - ¾® Et - O - Et (or)
CH 3 - CH 2 - Cl + EtS – ¾® CH 3 - CH 2 - S - Et
(c) Et - Cl + CH 3 O - ¾® Et - O - CH 3 (or)
(1m) ( 2m)
Et - Cl + CH 3 O - ¾® Et - O - CH 3
(2m) (1m)
Å
(d) Et - Br + Ph 3 P ¾® Et - PPh 3 (or)
Å
Et - Br + Ph 3 N ¾® E + - NPh 3
40. Among the following pair of reactions in which pair the second reaction is more reactive than
first in S N1 reaction ?
(a) Me 3 CCl + H 2 O ¾® Me 3 COH (or) Me 3 CBr + H 2 O ¾® Me 3 COH
(b) Me 3 CCl + CH 3 OH ¾® Me 3 C — OCH 3 (or) Me3C—Cl + H2O

Me3C—OH
(c) Me 3 CCl + H 2 O ¾® (or) Me 3 CCl + H 2 O
(1M) (2M)
(d) All of these
41. Which is a true statement concerning the transition state of an S N 2 reaction ?
(a) Closely resembles a carbocation intermediate
(b) The electrophile is responsible for the reaction
(c) Lower is energy than the starting materials
(d) Involves both the nucleophile and electrophile
42. Increasing the concentration of a nucleophile in a typical S N 2 reaction by a factor of 10 will
cause the reaction rate to :
(a) increase by a factor of 10 (b) increase by a factor of 10 2
(c) decrease by a factor of 10 (d) remain about the same
43. Decreasing the concentration of an electrophile in a typical S N 2 reaction by a factor of 3 will
cause the reaction ratio to :
(a) increase by a factor of 3 (b) increase by a factor of 3 2
(c) decrease by a factor of 3 (d) remain about the same

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44. Increasing the concentration of an electrophile in a typical S N 2 reaction by a factor of 3 and
the concentration of the nucleophile by a factor of 3 will change the reaction rate to :
(a) increase by a factor of 6 (b) increase by a factor of 9
(c) decrease by a factor of 3 (d) remain about the same
45. Consider the following reaction and select the best choice that represents the reaction.
CH3

H Na Å - SCH CH
¾ ¾¾¾¾¾
2
¾
3
® Product
Br
CH3 CH3 CH3

(a) H (b) H
SCH2CH3 SCH2CH3
CH3 CH3 CH3
SCH2CH3 S – CH2CH3
(c) (d)
H H
I
Me H
KSH
46. Et D ¾ ¾¾® Product; Identify the product.
H
SH H H SH
Me H Me H HS Me H Me
(a) Et D (b) Et D (c) Et D (d) Et D
H SH H H
47. The reaction ,
H OH H Cl
+ SOCl2 + SO2 + HCl

proceeds by the........... mechanism.

(a) S N i (b) S N 2 (c) S E 2 (d) S N1
48. Consider the following anions.
O O – O
O
–
CF3 – S – O
– C6H5 – S – O CH3 – C – O–
O
O
(I ) ( II ) (III) ( IV )

When attached to sp 3 -hybridized carbon, their leaving group ability in nucleophilic

substitution reaction decreases in the order :
(a) I > II > III > IV (b) I > II > IV > III (c) IV > I > II > III (d) IV > III > II > I

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Ph
H CH3 sr
Ph S N a
49. Cl H ¾ ¾¾¾® Principal organic product of the reaction will be :
S 2
N

Ph
Ph Ph
H CH3 H CH3
(a) PhS H (b) H SPh

Ph Ph

Ph Ph
Ph CH3 H CH3
(c) H Cl (d) H Ph

Ph Ph
50. Reaction of R-2-butanol with p-toluenesulphonyl chloride in pyridine followed by reaction
with LiBr gives:
(a) R-2-butyl bromide (b) S-2-butyl tosylate
(c) R-2-butyl tosylate (d) S-2-butyl bromide
51. The compound which undergoes S N1 reaction most rapidly is :

(a) Br (b) Br

(c) CH2Br (d) Br

52. Addition of KI accelerates the hydrolysis of primary alkyl halides because :

(a) KI is soluble in organic solvents
(b) the iodide ion is a weak base and a poor leaving group
(c) the iodide ion is a strong base
(d) the iodide ion is a powerful nucleophile as well as a good leaving group
53. Which of the following phrases are not correctly associated with S N1 reaction ?
(1) Rearrangement is possible
(2) Rate is affected by polarity of solvent
(3) The strength of the nucleophile is important in determining rate
(4) The reactivity series is tertiary > secondary > primary
(5) Proceeds with complete inversion of configuration
(a) 3, 5 (b) 5 only
(c) 2, 3, 5 (d) 3 only

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CH3

SO Cl NBS KSH
54. ¾ ¾¾¾® (A) ¾ ¾¾® (B) ¾ ¾¾® (C) , Product (C) is :
2 2
hv

SH SH Br Br

(a) Br (b) Cl (c) SH (d)

1 2 3
55. Energy profile diagram for an exothermic reaction, A ¾® B ¾® C ¾® D, is given below.
1
2
3

P.E. B C
A D
Progress of the reaction

The rate determining step of the reaction is :

(a) A ¾® B (b) B ¾® C (c) C ¾® D (d) can not predict

CH3

NBS
56. ¾¾® ( A)
Major

Major product (A) is :

Br Br
Br
(a) (b) (c) (d)

Br
Cl LiBr /DMSO
57. ¾ ¾¾¾¾® Major product (X)
S 2 conditions
Cl N

The product X is :

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Br Cl
(a) (b)
Cl Br

Br Cl
(c) (d)
Br
58. Relative rate of reaction of the following amine with methyl iodide is:

N N
N N
(A) (B) (C)

(a) A > B > C (b) A > C > B (c) B > C > A (d) B > A > C

H
OTs
PhCH2O C H
C NaI
59. C OCH3 ¾ ¾¾¾¾¾¾
¾®
H Dimethyl sulfoxide
H
OCH3

Major product which you expect in the above reaction is :

H H
I OTs I
C OCH2Ph C
H H
C C
(a) C OCH3 (b) C OCH3
H H
H H
OCH3 OCH3
I
H
H OTs
OCH2Ph C OCH2Ph
H C
C C I
(c) C OCH3 (d) C H
H H
H H
OCH3
OCH3
HS H HS
NaOH in
(A) +
60. aqueous EtOH
(major)
C6H10S
H Cl H
Major product of the above reaction is :
HS SH
S

(a) (b) S (c) (d)

H OH

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61. CH3 — C — C14 — CH3 ¾¾® Major product of the reaction is:
D
CH3 OTs
Ph
CH3 14 Ph 14
(a) C C (b) CH3 — C — CH CH2
CH3 CH3
CH3

CH3 Ph CH3 Ph
14 C
(c) C C (d) C
CH3 CH3 CH3 CH3
14

62. The decreasing order of reactivity of the compounds given below towards solvolysis under
identical conditions is :
Cl Cl
| |
CH3 – C – CH3 CH3 – C – CH3
Cl
|
CH3 – C – CH3
H3C

(I) (II) (III)

(a) II > III > I (b) I > II > III (c) III > II > I (d) II > I > III

OH
1. One Eq. NaOH
63. OH ¾¾¾¾¾¾¾¾®
2. MeBr
(A); Product (A) is :

OMe OH OH

(a) OH (b) OMe (c) (d) None of these

64. ( R )-2-octyl tosylate is solvolyzed in water under ideal S N1 conditions. The product(s) will
be:
(a) R-2-octanol and S-2-octanol in a 1 : 1 ratio
(b) R-2-octanol and S-2-octanol in a 1.5 : 1 ratio
(c) R-2-octanol only
(d) S-2-octanol only

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65. From each of the following pairs select the compound that will react faster with sodium
iodide in acetone :
Pair-A: (1) 2 - Chloropropane (2) 2 - Bromopropane

Pair-B: (3) 1 - Bromobutane (4) 2 - Bromobutane

(a) 1, 3 (b) 1, 4 (c) 2 , 3 (d) 2 , 4

66. Among the given halides, which one will give same product in both S N1 and S N 2 reactions.
CH 3
| CH3
(I) CH 3 - CH - CH 2 - CH - CH 3 (II)
|
Br Cl
Cl
(III) (IV) CH 3 - CH - Br
|
Et
(a) (III) only (b) (I) & (II) (c) (III) & (IV) (d) (I), (III) & (IV)
67. Product(s) formed during this reaction is/are :
*
CH2 – CH2 – OTs
AcONa
¾® Product ? [ C * = isotopic carbon]
¾ ¾¾
AcOH
* – CH – OAc
CH * – OAc
CH2 – CH
2 2 2
(a) (b)

*
CH2 – CH2 – OTs
(c) (d) Both (a) & (b)

OAc
excess HI (conc.)
68. Anisole ¾ ¾¾¾¾¾¾® Product
reflux

(a) I + CH3I (b) I + CH 3OH

(c) OH + CH 3I (d) OH + CH 3CH2I

69. Which of the following compounds would react faster with NaCN in an S N 2 reaction ?
OMe
(a) (b) OTs (c) MeO (d) OTs

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70. HC ºº CNa + Cl – CH 2 – CH 2 – CH 2 – I ¾® (A); Major product (A) is :
(a) H – C º C – CH 2 – CH 2 – CH 2 – I (b) CH 2 = CH – CH 2 – I
(c) H – C º C – CH 2 – CH 2 – CH 2 – Cl (d) CH 2 = CH – CH 2 – Cl
71. What is the major product obtained in the following reaction ?
Et2O
SNa + CH3 — Br Product.

(a) (b) Br (c) S (d)

CH3

Br CH3 S 2
72. + OH - ¾ ¾
N
¾® A; The product A is :
H H
HO CH3 H CH3

(a) H H (b) HO H

(c) Both (a) and (b) are correct (d) None is correct

H 2O
73. Me 2 C = CH – CH 2 – CH 2 – Cl ¾¾¾¾® ( X ); Major product of the reaction is :
CaCO 3

OH
|
(a) Me – C – CH 2 – CH 2 – CH 2 (b) Me 2 C = CH – CH 2 – CH 2 – OH
|
Me
OH
(c) Me 2 C = CH – CH – CH 2 – OH (d) CMe2
|
OH
OH OH
HBr HBr
74. ¾ ¾¾® ( A) , ¾ ¾¾® ( B )
D D

CH2OH OCH3
Product (A) and (B) respectively are :

OH OH OH OH
(a) and (b) and

CH2Br Br CH2Br OH

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OH Br Br Br
(c) and (d) and

CH2Br OH CH2OH OCH3

75. Relative rate of reaction with H 2 O.

H ONS H ONS H ONS

CH3 CH3

(i) (ii) CH3 (iii)

æ O ö
ç || ÷
ç —ONS == —O — S NO 2 ÷
ç || ÷÷
ç O ø
è
(a) (i) > (ii) > (iii) (b) (ii) > (i) > (iii)
(c) (iii) > (ii )> (i) (d) (iii) > (i) > (ii)

O O
2 eq. KNH n—C H — Br
76. ¾ ¾¾¾¾
2
® ¾ ¾¾¾¾¾
4 9
® (P) ;
NH 3 ( l ) then H 3O Å

End product (P) of the above reaction is :

O O O O

(a) (b)

O O O O

(c) (d)

77. Which of the following statements is correct regarding the rate of hydrolysis of the
compounds (A) and (B) by S N1 reaction ?

Br O Br
A B

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(a) A reacts faster than B (b) B reacts faster than A
(c) Both A and B reacts at the same rate (d) Neither A nor B reacts
78. What are reactant X and product Y in the following sequence of reactions ?

O
O
H3C SCl
H3C O S CH3
O NaN3
Reactant X Pyridine Ethanol-water
Product Y
H H O

Reactant X Product Y
H3C OH N3
(a)
H H H H

H3C OH H
(b)
H H H N3

H3C H H
(c)
H OH H N3

H3C H N3
(d)
H OH H H

79. Transition state of given S N 2 is :

CH2—Br CH2—O—R
R-O–
SN2 reaction

+
+ d (+) +
+
ds
OR OR
H H
(a) (b)
H H
Br Br
dr d (+)

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+
+ d (–) +
+
dr
OR OR
H H
(c) (d)
H H
Br Br
ds d (–)

80. C 6 H 13 Br + OH - ¾® C 6 H 13 OH + Br - is an example of:

(a) Nucleophilic addition (b) Nucleophilic substitution
(c) Electrophilic addition (d) Electrophilic substitution
(e) Free radical substitution
81. Transition state 2 is structurally most likely as :

T.S.2 T.S.3

intermediate 2
T.S.1

E
intermediate 1

product
reactant

(a) intermediate 1 (b) transition state 3

(c) intermediate 2 (d) product
O
CH2

82. O O

x = Number of aromatic compound obtained when above compound undergo complete

acidic hydrolysis.
(a) 1 (b) 2 (c) 3 (d) 4
83. S N 1 and S N 2 reactions are
(a) Both stereospecific
(b) Both stereoselective
(c) Stereoselective and stereospecific respectively
(d) Stereospecific and stereoselective respectively

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84. Most reactive compound toward S N 1 is :

CH2—I CH2—I CH2—I CH2—I

(a) (b) (c) (d)

CH
C

1. NaNH 2 ( 2 eq.)
2. CH 3CH 2 — I
85. ¾ ¾¾¾¾¾¾® Product ( X ) is :
3. CH 3 — I
4. H 2 / Pd - BaSO 4
OH
CH3CH2
CH3CH2

(a) (b)
OCH3
CH2—O—CH3
CH3
CH3

(c) (d)
O—CH2CH3
CH2—OCH2CH3
86. Following reaction is an example of :

+ R2NH
O

(a) S N 2 Reaction (b) S N 1 Reaction

(c) Electrophilic Addition (d) S N – NGP
87. The major product of the following reaction :
OH
| HBr
[x]
Br H
| |
(a) (b) (c) (d)
OH
Br
88. Choose the suitable option for the correct mechanism for the following reactions.

CH3OH
(I) + CH3O (II) + CH3OH
Br high Br
concentration

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(a) S N 1, S N 1 (b) S N 1, S N 2 (c) S N 2, S N 1 (d) S N 2, S N 2
O O
H+
89. Reaction 1
HO O OMe
O
O
O O

N3–
O O Reaction 2
Br N3

Types of mechanism followed by reaction 1 and reaction 2 respectively.

(a) S N 1, S N 1 (b) S N 2, S N 2 (c) S N 1, S N 2 (d) S N 2, S N 1
OTs OTs
90.
H2S
Product
KOH

Product of above reaction will be :

OTs SH OTs SH

(a) (b) (c) (d)

S S

ANSWERS — LEVEL 1
1. (a) 2. (b) 3. (c ) 4. (a) 5. (b) 6. (b) 7. (b) 8. (d)
9. (b) 10. (a) 11. (c) 12. (a) 13. (d) 14. (d) 15. (b) 16. (c)
17. (a) 18. (a) 19. (c) 20. (d) 21. (b) 22. (a) 23. (c) 24. (c)
25. (d) 26. (d) 27. (d) 28. (a) 29. (a) 30. (d) 31. (b) 32. (d)
33. (d) 34. (c) 35. A(a) 35. B(b) 36. (d) 37. (b) 38. (d) 39. (b)
40. (d) 41. (d) 42. (a) 43. (c) 44. (b) 45. (c) 46. (d) 47. (a)
48. (b) 49. (b) 50. (d) 51. (b) 52. (d) 53. (a) 54. (b) 55. (a)
56. (a) 57. (b) 58. (c) 59. (c) 60. (b) 61. (c) 62. (d) 63. (a)
64. (b) 65. (c) 66. (d) 67. (d) 68. (c) 69. (d) 70. (c) 71. (c)
72. (b) 73. (d) 74. (b) 75. (c) 76. (d) 77. (b) 78. (b) 79. (d)
80. (b) 81. (c) 82. (b) 83. (b,c) 84. (d) 85. (b) 86. (a) 87. (c)
88. (c) 89. (c) 90. (b)

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