Bromination
Benzene undergoes bromination with a halogen carrier catalyst to form bromobenzene.
- Reagents
- Br2 and FeBr3 or AlBr3
- Conditions
- anhydrous halogen carrier catalyst
- Reaction class
- electrophilic substitution
- Equation
- C6H6 + Br2 -> C6H5Br + HBr
Overview
Benzene undergoes bromination with a halogen carrier catalyst to form bromobenzene.
Transformation
- Equation
- C6H6 + Br2 -> C6H5Br + HBr
- Reagents
- Br2 and FeBr3 or AlBr3
- Environment
- anhydrous halogen carrier catalyst
- Reaction class
- electrophilic substitution
- Mechanism
- electrophilic aromatic substitution
- Evidence level
- textbook core
Scope and limitations
- Scope
- Benzene reacts with bromine when a halogen carrier generates a sufficiently strong electrophile.
- Limitations
- Benzene does not rapidly decolourise bromine water without a catalyst; substitution patterns of substituted arenes are not covered here.
Related reactions
- Combustion: Benzene → Carbon dioxide
Benzene combusts to carbon dioxide and water and tends to burn with a smoky flame.
- 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.
- Friedel Crafts acylation: Benzene → Acylbenzenes
Friedel-Crafts acylation attaches an acyl group to benzene.
- Ring hydrogenation: Benzene → Cyclohexane
Benzene gives cyclohexane through ring hydrogenation.
- Nitration: Benzene → Nitrobenzene
Benzene gives nitrobenzene through nitration.
References
- Organic Chemistry: Electrophilic Aromatic Substitution Reactions: BrominationJohn McMurry · OpenStax Organic Chemistry · 2023
Supports FeBr3-mediated polarization of bromine, arenium-ion formation, and deprotonation that restores aromaticity in benzene bromination.