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Electron-poor aromatic rings containing a leaving group can undergo substitution with electron-rich nucleophiles.the mechanism proceeds through addition of a nucleophile to the aromatic ring (via an electron-rich intermediate) followed by loss of a leaving group, in a process sometimes called, “addition-elimination”.
The only substitution product is the one where the nucleophile ends up attached to the same carbon as that bearing the leaving group. (This differentiates it from electrophilic aromatic substitution, where a mixture of ortho-, para– and meta- products can be obtained.)
treating chlorobenzene with sodium amide (NaNH2) in liquid ammonia (boiling point = –33°C) resulted in the rapid formation of aminobenzene (“aniline”)
