Hydrolysis
Replacing the carbon-bromine bond with carbon-oxygen bonding produces propan-2-ol. Its central carbon remains secondary, explaining its subsequent oxidation to propanone.
- Reagents
- Aqueous NaOH or KOH
- Conditions
- Warm in aqueous alkali
- Reaction class
- Hydrolysis
- Equation
- CH3CHBrCH3 + OH- -> CH3CH(OH)CH3 + Br-
Overview
Replacing the carbon-bromine bond with carbon-oxygen bonding produces propan-2-ol. Its central carbon remains secondary, explaining its subsequent oxidation to propanone.
Transformation
- Equation
- CH3CHBrCH3 + OH- -> CH3CH(OH)CH3 + Br-
- Reagents
- Aqueous NaOH or KOH
- Environment
- Warm in aqueous alkali
- Reaction class
- Hydrolysis
- Mechanism
- nucleophilic substitution
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- Secondary haloalkane undergoing substitution at its central carbon.
- Limitations
- Elimination to propene competes with substitution; solvent and conditions affect the pathway balance.
Related reactions
- Oxidation: Propan-2-ol → Propanone
Propan-2-ol is oxidised to propanone.
- Reduction: Propanone → Propan-2-ol
Propanone is reduced to propan-2-ol.
- Hydration: Propene → Propan-2-ol
Propene gives propan-2-ol through hydration.
- Hydrobromination: Propene → 2-Bromopropane
Protonation of propene favours the secondary carbocation over a primary one. Bromide then forms the C-Br bond at the central carbon.
References
- Pearson Edexcel International Advanced Level Chemistry Scheme of WorkPearson Education Limited · Pearson qualifications · 2018
Official Pearson teaching guidance specifying chloroalkane-relevant conditions: aqueous alkali, ethanolic potassium hydroxide, alcoholic ammonia, alcoholic potassium cyanide, and PCl5 alcohol chlorination.