Bromination
Phenol decolourises bromine water and forms a pale precipitate of 2,4,6-tribromophenol.
- Reagents
- bromine water
- Conditions
- room temperature; no halogen carrier
- Reaction class
- electrophilic substitution
- Equation
- C6H5OH + 3 Br2 -> C6H2Br3OH + 3 HBr
Overview
Phenol decolourises bromine water and forms a pale precipitate of 2,4,6-tribromophenol.
Transformation
- Equation
- C6H5OH + 3 Br2 -> C6H2Br3OH + 3 HBr
- Reagents
- bromine water
- Environment
- room temperature; no halogen carrier
- Reaction class
- electrophilic substitution
- Mechanism
- electrophilic aromatic substitution
- Evidence level
- textbook core
Scope and limitations
- Scope
- The hydroxyl group activates phenol, allowing rapid 2,4,6-tribromination with bromine water.
- Limitations
- This record represents excess aqueous bromine; controlled monobromination requires different conditions.
References
- Organic Chemistry: Reactions of PhenolsJohn McMurry · OpenStax Organic Chemistry · 2023
Supports the hydroxyl group as a strongly activating, ortho- and para-directing substituent in electrophilic aromatic halogenation of phenols.