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Question:

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

Solution:

Out of chlorobenzene and benzyl chloride, benzyl chloride gets easily hydrolysed by aqueous NaOH. In benzyl chloride, C6H5−CH2−Cl, the chlorine atom is attached to an aliphatic C atom. In chlorobenzene, C6H5−Cl, the chlorine atom is attached to an aromatic C atom. The cleavage of the bond between the chlorine atom and the aliphatic C atom is much easier than the cleavage of the bond between the chlorine atom and the aromatic C atom. The bond between the chlorine atom and the aliphatic C atom is a single bond. The bond between the chlorine atom and the aromatic C atom has partial double bond character due to resonance. The lone pair of electrons on the Cl atom are delocalized over the benzene ring through resonance.