3. many electrophilic aromatic halogenations require the presence of an aluminum halide (aluminum chloride or aluminum bromide) as a catalyst. why is it unnecessary to include an aluminum halide in the electrophilic aromatic bromination reaction of acetanilide with molecular bromine.

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21-10-2022
Chemistry

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3. many electrophilic aromatic halogenations require the presence of an aluminum halide (aluminum chloride or aluminum bromide) as a catalyst. why is it unnecessary to include an aluminum halide in the electrophilic aromatic bromination reaction of acetanilide with molecular bromine.

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lukanov1901 lukanov1901 · Answer 1 · 2022-11-01T18:31:25+01:00

The aluminum halide is used to increase the electrophilicity of the halogen, in electrophilic aromatic substitutions which is unnecessary because acetanilide is a very good nucleophile.

In electrophilic aromatic substitutions, the aromatic ring acts as the nucleophile, while the other component (halogen, alkyl halide, acyl halide, etc.) acts as the electrophile. The halogen molecules are not great electrophiles, so aluminum halide is added to facilitate the reaction.

However, the nucleophilicity of the aromatic ring can be increased through resonance and inductive effects of the substituents, and in acetanilide the electron-donating amide group is effective enough to make the aromatic ring a good enough nucleophile to, in turn, make the use of aluminum halide unnecessary.

You can learn more about electrophilic aromatic substitutions here:

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