A) allyl chloride
B) ethyl chloride
C) isopropyl chloride
D) benzyl chloride
Correct Answer: D
Solution :
\[{{\text{S}}_{\text{N}}}\text{1}\]mechanism involves forma4aon of arbocations and the order of stability of carbocations is as \[\text{(}{{\text{C}}_{2}}\text{H}_{5}^{+}\text{)}\,\text{(C}{{\text{H}}_{3}}{{\text{)}}_{2}}\overset{+}{\mathop{C}}\,H<\overset{+}{\mathop{C}}\,{{H}_{2}}-CH\] \[=C{{H}_{2}}<{{C}_{6}}{{H}_{5}}CH_{2}^{+}\] Thus, benzyl chloride, due to the formation of benzyl carbocation (most stable), readily undergoes hydrolysis by \[{{\text{S}}_{\text{N}}}\text{1}\]mechanism.
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