Friedel-Crafts Acylation of Benzene

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Presentation transcript:

Friedel-Crafts Acylation of Benzene The acyl group is typically derived from an acid chloride 16.4 Electrophilic Aromatic Substitution Reactions of Benzene

Friedel-Crafts Acylation of Benzene Mechanism: 16.4 Electrophilic Aromatic Substitution Reactions of Benzene

Friedel-Crafts Acylation of Benzene In contrast to the alkylation version, one equivalent of AlCl3 is required 16.4 Electrophilic Aromatic Substitution Reactions of Benzene

Intramolecular Friedel-Crafts Reactions Both the alkylation and acylations can occur intramolecularly The reaction occurs at an ortho position and is best for five- and six-membered rings 16.4 Electrophilic Aromatic Substitution Reactions of Benzene

Problems Identify the carboxylic acid chloride that might be used in a Friedel-Crafts acylation for the following acylbenzenes:

Draw the complete mechanism for the acylation of 4-phenylbutanoylchloride