Out of chlorobenzene and benzyl chloride, which one gets easily hydrolysed by aqueous NaOH and why?

Explanation

In cholorobenzene `C_(6)H_(5)Cl`, an unshared pair of electrons on the Cl-atom, is involved in resonance with the ring `pi`-electrons. As a result, the C-Cl bond acquires some double bond character. Thus, the C-Cl bond becames much stronger and expulsion of the Cl -atom form the ring cannot be affected easily. So, it is not easy to hydrolyse chlorobenzene.

On the other hand, the C-Cl bond in benzyl chloride `(Ph-CH_(2)-Cl)` is unable to acquire any double bond character because similar electron delocalisation is not possible. Thus, it is easy to hydrolyse benzyl chloride.