Haloalkanes And Haloarenes Ques 9

9. Which of the following undergoes nucleophilic substitution exclusively by $S_N 1$ mechanism?

[2005]

(a) Ethyl chloride

(b) Isopropyl chloride

(c) Chlorobenzene

(d) Benzyl chloride

Show Answer

Solution:

  1. (d) $S_N 1$ reaction is favoured by heavy groups on the carbon atom attached to halogen i.e Benzyl $>$ allyl $>$ tertiary $>$ secondary $>$ primary $>$ alkyl halides

Obtained from $S_N 1$ path.

(Benzyl cation)

This molecule is resonance stabilised.



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