Replacement of $ \mathrm{Cl} $ of Chlorobenzene to give phenol requires drastic conditions, but $ \mathrm{Cl} $ of $ 2,4 $ - dinitro chlorobenzene is readily replaced. This is because,

Question

Replacement of $ \mathrm{Cl} $ of Chlorobenzene to give phenol requires drastic conditions, but $ \mathrm{Cl} $ of $ 2,4 $ - dinitro chlorobenzene is readily replaced. This is because,, $ -\mathrm{NO}_{2} $ group makes the ring electron rich at o- and p- positions., $-\mathrm{NO}_{2} $ group withdraws electrons from $ \mathrm{m} $-position., $ -\mathrm{NO}_{2} $ donate electrons at $ \mathrm{m} $ - position., $ -\mathrm{NO}_{2} $ withdraws electrons from o- and p-positions.

MARKS App · Accepted Answer

The reaction involved is The presence of $ -\mathrm{NO}_{2} $ group at o- and p- positions withdraws electron density from the benzene ring, therefore, facilitates the attack of the nucleophile on haloarenes. Thus, the carbanion formed, is stabilized through resonance as shown below:

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