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Q. The most easily hydrolysed molecule under $ S_N1$ conditions is

J & K CETJ & K CET 2009Haloalkanes and Haloarenes

Solution:

$S _{ N } 1$ mechanism involves formation of cations and the order of stability of carbocations is as
$(C_2H_5^+)(CH_3)_2\overset{+}{C}H < \overset{+}{C} H_2 - CH = CH_2 < C_6H_5CH_2^+$
Thus, benzyl chloride, due to the formation of benzyl carbocation (most stable), readily undergoes hydrolysis by $S _{ N } 1$ mechanism.