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Friedel-Crafts Acylation

If a carbocation is generated from an acyl halide or an anhydride, the SEAr on benzene leads to an alkyl phenyl ketone.

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Friedel-Crafts acylation: benzene with an acyl halide or an anhydride, AlCl₃ and then H₂O/H⁺, gives an alkyl phenyl ketone

The Lewis acid coordinates to the basic centers of the acyl halide or the anhydride and forces the halogen or carboxylate, respectively, to leave giving rise to a carbonyl carbocation whose positive charge is stabilized by the electron lone pairs of the oxygen.

Formation of the acyl cation: AlCl₃ coordinates to the acyl halide or the anhydride and causes the leaving group to depart; the cation is stabilized by resonance with the oxygen

The carbonyl carbocation is attacked by the aromatic ring, yielding an alkyl phenyl ketone.

Carbonyl cations, stabilized by the oxygen, do not rearrange.

The carbonyl group attached to the benzene makes the latter less electron rich and much less reactive thus avoiding polyacylation.

The acyl cation is attacked by the ring; after loss of HX or RCOOH the ketone is obtained, complexed with AlCl₃ and strongly deactivated towards a second SEAr