Friedel Crafts acylation
Friedel-Crafts acylation attaches an acyl group to benzene.
- Reagents
- acyl chloride and anhydrous AlCl3
- Conditions
- anhydrous conditions, heat under reflux if required
- Reaction class
- electrophilic substitution
- Equation
- C6H6 + RCOCl -> C6H5COR + HCl
Overview
Friedel-Crafts acylation attaches an acyl group to benzene.
Transformation
- Equation
- C6H6 + RCOCl -> C6H5COR + HCl
- Reagents
- acyl chloride and anhydrous AlCl3
- Environment
- anhydrous conditions, heat under reflux if required
- Reaction class
- electrophilic substitution
- Mechanism
- Friedel-Crafts acylation
- Evidence level
- textbook core
Scope and limitations
- Scope
- Benzene reacts with acyl chlorides using aluminium chloride to form aromatic ketones.
- Limitations
- The product ring is deactivated, so multiple acylation is less likely; strongly deactivated rings do not react readily.
Related reactions
- Combustion: Benzene → Carbon dioxide
Benzene combusts to carbon dioxide and water and tends to burn with a smoky flame.
- Bromination: Benzene → Halogenoarenes
Benzene undergoes bromination with a halogen carrier catalyst to form bromobenzene.
- Nitration: Benzene → Nitroarenes
Benzene is nitrated by concentrated nitric and sulfuric acids to form nitrobenzene.
- Friedel Crafts alkylation: Benzene → Alkylarenes
Friedel-Crafts alkylation attaches an alkyl group to benzene.
- Ring hydrogenation: Benzene → Cyclohexane
Benzene gives cyclohexane through ring hydrogenation.
- Nitration: Benzene → Nitrobenzene
Benzene gives nitrobenzene through nitration.
References
- Organic Chemistry: Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts ReactionJohn McMurry · OpenStax Organic Chemistry · 2023
Supports AlCl3-assisted formation of alkyl and acylium electrophiles, aromatic sigma-complex formation and deprotonation; also records carbocation rearrangement and polyalkylation boundaries for Friedel–Crafts alkylation.