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Q.

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

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a

chlorobenzene

b

isopropyl chloride

c

benzyl chloride

d

ethyl chloride

answer is D.

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Detailed Solution

Benzyl chloride only undergoes nucleophilic substitution through the SN1 mechanism.
This is due to the fact that when the chloride ion is removed, the positive charge on the benzyl cation is stabilised by resonance with the aromatic nucleus.

The reaction would be

Question Image

Hence the correct option (D).benzyl chloride

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