3.4.6 Aromatic Chemistry - Friedel.Crafts acylation reactions

Specification

Students should:
  • understand that Friedel-Crafts acylation reactions are important steps in synthesis
  • understand the mechanism of acylation using AlCl3 as catalyst

Friedel-Crafts acylation

Friedel Crafts catalysis involves the use of aluminium chloride to polarise chlorine containing compounds, making them susceptible to electrophilic substitution in aromatic compounds.

Acylation means substitution of an alkyl group attached to a carbonyl group. This is a useful way of introducing a carbon chain with a reactive functional group onto an aromatic ring.

The reaction is as follows:

acylation of benzene using a Friedel Crafts catalyst

The aluminium trichloride is electron deficient and behaves as a Lewis acid. It can accept an electron pair from the chlorine atom in other chlorine containing molecules. Aluminium chloride is an example of a Friedel-Crafts catalyst:

Friedel Crafts catalysis using aluminium chloride


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