Addition-Elimination Substitution on Aromatic Chloride Facilitated by a para-nitro group

Sn2

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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.

Related Halex reaction and alternative benzyne intermediate mechanism.

See the effect of two nitro groups

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

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