Question

In normal reaction conditions, chlorobenzene does not react with NaOH, but 1-

chloro-4-nitrobenzene reacts with NaOH in these conditions. Explain.

Answer 1

When the reaction with chloro-4-nitrobenzene occurs, SNAr mechanism takes place, because Meisenheimer's intermediate is stabilized by resonance, which is impossible with regular chlorobenzene.