Question

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

Answer 1

chlorine is directly attached to benzene ring in benzyl chloride. It gives rise to its more stability. Chlorine has lone pair and chlorobenzene can undergo resonance easily.  Benzyl carbocation is very stable because of resonance. It is the most stable carbocation.  Though the intermediate is more stable benzyl chloride has a tendency to be converted into benzyl carbocation always.

so, Benzyl chloride is more easily hydrolysed by aqueous NaOH than that of chlorobenzene.

Answer 2

The answer is Benzyl chloride can get easily hydrolysed as compared to Chloro benzene.

This is due to the stability of Chloro benzene. In chloro benzene, chlorine is directly attached to the benzene ring with a double bond which is the reason for the resonating structure of chloro benzene and provides stability to the bond and structure.

But in case of Benzyl Chloride, it can easily undergo SN1 reaction to form benzyl carbocation.

Although benzyl carbocation is very stable but benzyl chloride always undergoes SN1 reaction and form it whenever subjected to hydrolysis with aqueous NaOH.