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

1. Ethyl chloride
2. Isopropyl chloride
3. Chlorobenzene
4. Benzyl chloride

Correct answer: Benzyl chloride

Solution

Benzyl chloride undergoes nucleophilic substitution via the SN1 mechanism because the benzyl carbocation formed during the reaction is highly stabilized by resonance. Other options either lack such stabilization or follow different mechanisms.

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