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Question
Out of chlorobenzene and benzyl chloride, which one gets easily hydrolysed by aqueous NaOH and why?
Solution
Chlorobenzene does not undergo hydrolysis readily at room temperature because of the stability of the phenyl cation. The phenyl cation is unstable than the benzyl cation because of partial double bond character in the C-H bond. Benzyl carbocation being resonance stabilised can easily release the Cl and thus get hydrolysed. Therefore, out of chlorobenzene and benzyl chloride, benzyl chloride gets easily hydrolysed by aqueous NaOH whereas chlorobenzene doesn't.
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