Addition-Elimination Substitution on Aromatic Chloride

Facilitated by a para-nitro group

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The hydroxide anion attacks para to the nitro group. The negative charge is delocalised around the ring to the nitro group which helps stabilise the transition state. The chloride anion is then eliminated.

See the effect of two nitro groups

M. Mąkosza, Russ. Chem. Bull., 1996, 45, 491–504.