Which of the following undergoes nucleophilic substitution exclusively by $S_{N} 1$ mechanism?

Ethyl chloride

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Isopropyl chloride

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Benzyl chloride

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Chloro benzene

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Solution

The correct option is C Benzyl chloride
Benzyl chloride undergoes nucleophilic substitution exclusively by $S_{N} 1$ mechanism.
This is because when chloride ion is lost, the positive charge on benzyl cation is stablized by resonance with aromatic nucleus.
$C_{6} H_{5} - C H_{2} - C l ⟶ C_{6} H_{5} - \oplus C H_{2} + Θ C l$

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