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Haloalkanes And Haloarenes

Question
CBSEENCH12008009

Explain the reason for the following:

Unlike the chlorine atom in CH3Cl, that in chlorobenzene, C6H5Cl is not easily replaced by the -OH group.

Solution

Chlorine in chlorobenzene is not easily replaced by -OH group because of resonace effect. In chlorobenzene the electron pairs are in conjugation with pi-electrons of the ring. C-Cl bond acquires a partial double bond character due to resonace. As a result, the bond cleavage in chlorobenzene is difficult than chloromethane.