Question

The most easily hydrolysed molecule under $S_{N}1$ conditions is

• A. Allyl chloride
• B. Ethyl chloride
• C. Isopropyl chloride
• D. Benzyl chloride

Answer 1

Answer: (D)

Benzyl chloride

$S_{N}1$ mechanism involves the formation of carbocations and the order of stability of carbocations is as

$\left(C_2{H}_5^{+}\right)<(C{H}_3{)}_2\stackrel{+}{C}H<\stackrel{+}{C}{H}_2-CH=C{H}_2<C_6{H}_{5}C{H}_2^{+}$

Thus, benzyl chloride, due to the formation of benzyl carbocations (most stable), readily undergoes hydrolysis by $S_{N}1$ mechanism.

.

Hence, the correct option is D