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In order to regenerate the aromatic ring, a proton is lost at the sp3 hybridized carbon. Thus, p-Nitroaniline can be prepared by means of electrophilic aromatic substitution.
To begin, nitric acid needs to be activated as it has little electrophilic power. Thus, concentrated sulfuric acid is added to protonate the nitric acid. Dehydration produces the nitronium ion, which is a strong electrophile and has most of its positive charge on the nitrogen atom. The nitronium ion, acting as the electrophile in the nitration reaction, will attack the benzene ring and produces the nitrobenzene ring. Resonance-stabilized arenium ion is created when the nucleophilic carbon pi bond on the acetanilide reacts with the nitronium ion...
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