Which of the following undergoes nucleophilic | vedclass

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(D) $S_N1$ mechanism proceeds via the formation of a carbocation intermediate. The stability of the carbocation determines the reactivity. Benzyl chlo

Vedclass · Accepted Answer

Benzyl chloride

Vedclass · Answer

(D) $S_N1$ mechanism proceeds via the formation of a carbocation intermediate. The stability of the carbocation determines the reactivity. Benzyl chloride $(C_6H_5CH_2Cl)$ forms a benzyl carbocation $(C_6H_5CH_2^+)$,which is highly stabilized by resonance with the benzene ring. Ethyl chloride $(CH_3CH_2Cl)$ and isopropyl chloride $(CH_3CHClCH_3)$ primarily undergo $S_N2$ or a mixture of $S_N1/S_N2$ mechanisms depending on conditions,but they are not exclusive $S_N1$ substrates. Chlorobenzene does not undergo nucleophilic substitution under normal conditions due to partial double bond character in the $C-Cl$ bond. Therefore,benzyl chloride is the correct answer as it forms a stable carbocation.

Which of the following undergoes nucleophilic substitution exclusively by $S_N1$ mechanism?

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