Haloalkanes and Haloarenes - Result Question 17

####17. Which of the following undergoes nucleophilic substitution exclusively by SN1 mechanism?

[2005]

(a) Ethyl chloride

(b) Isopropyl chloride

(c) Chlorobenzene

(d) Benzyl chloride

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Solution:

  1. (d) SN1 reaction is favoured by heavy groups on the carbon atom attached to halogen i.e Benzyl > allyl > tertiary > secondary > primary > alkyl halides

Obtained from SN1 path.

(Benzyl cation)

This molecule is resonance stabilised.



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