NCERT Class XII Chemistry
Chapter - Haloalkanes and Haloarenes
Questions with Solutions

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Question : 29
Total: 31
Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism? Explain your answer.
(i) CH3CH2CH2CH2Br or CH3CH2
C
|
Br
H
C
H3

(ii) CH3CH2
C
|
Br
H
C
H3
or H3C
CH3
|
C
|
CH3
Br

(iii) CH3
C
|
CH3
H
C
H2
CH2
Br
or CH3CH2
C
|
CH3
H
C
H2
Br
Solution:  
We know that SN2 mechanism involves a transition state wherein both, the incoming nucleophile as well as the leaving group are present around the carbon atom. There are 5 atoms simultaneously bonded to it. Thus, for such a transition state to be possible,there should be minimum steric hindrance. Hence, 1° alkyl halides are most reactive towards SN2 followed by 2° and finally 3°.
1° RX > 2° RX > 3° RX
Based on the above order,
(i) CH3CH2CH2CH2Br is more reactive.
(ii) CH3CH2
C
|
Br
H
C
H3
is more reactive.
(iii) CH3
C
|
CH3
H
CH2
CH2
Br
is more reactive.
In (iii), it is the proximity of the branched chain CH3 that determines the reactivity. In CH3CH2CH(CH3)CH2 the methyl group is closer to the leaving group thereby hindering the transition state.
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