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Question : 17
Total: 30
Which alkyl halide from the following pair is chiral and undergoes faster S N 2 reaction?
S N 1 and S N 2 , which reaction occurs with
(a) Inversion of configuration
(b) Racemisation
(ii) Out of
(a) Inversion of configuration
(b) Racemisation
Solution:
(i) S N 2 reaction occurs more quickly in primary alkyl halides than in secondary and tertiary alkyl halides.
(a) is primary alkyl halide and (b) is secondary alkyl halide.
So, (a) undergoesS N 2 reaction faster than (b).
(ii) Out ofS N 1 and S N 2 , which reaction occurs with:
(a) Inversion of configuration:S N 2 , because the incoming nucleophile attacks from the backside resulting in inversion of configuration.
(b) Racemisation:S N 1 , in this first carbocation is formed.
The incoming nucleophile can attack from either side resulting in racemic mixture.
(a) is primary alkyl halide and (b) is secondary alkyl halide.
So, (a) undergoes
(ii) Out of
(a) Inversion of configuration:
(b) Racemisation:
The incoming nucleophile can attack from either side resulting in racemic mixture.
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