Ketone reduction
Hydride adds to the planar carbonyl carbon while the pi electrons move onto oxygen. Subsequent protonation gives cyclohexanol; the existing carbon ring remains intact.
- Reagents
- NaBH4; aqueous work-up
- Conditions
- Suitable alcohol solvent followed by protonation
- Reaction class
- Ketone reduction
- Equation
- C6H10O + 2[H] -> C6H11OH
Overview
Hydride adds to the planar carbonyl carbon while the pi electrons move onto oxygen. Subsequent protonation gives cyclohexanol; the existing carbon ring remains intact.
Transformation
- Equation
- C6H10O + 2[H] -> C6H11OH
- Reagents
- NaBH4; aqueous work-up
- Environment
- Suitable alcohol solvent followed by protonation
- Reaction class
- Ketone reduction
- Mechanism
- nucleophilic hydride addition
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- Hydride adds to the ketone carbonyl.
- Limitations
- Reduction removes C=O unsaturation without opening the carbon ring.
Related reactions
- Dehydration: Cyclohexanol → Cyclohexene
Cyclohexanol gives cyclohexene through dehydration.
- Secondary alcohol oxidation: Cyclohexanol → Cyclohexanone
Oxidation removes hydrogen from the O-H group and its attached carbon, creating a C=O bond. Because that carbon already bonds to two other carbons, the product is a ketone and the six-membered ring is retained.
References
- Organic Chemistry: Nucleophilic Addition of Hydride and Grignard ReagentsJohn McMurry · OpenStax Organic Chemistry · 2023
Supports hydride addition to aldehydes and ketones followed by protonation to form alcohols; used as the mechanism-pattern source for the aldehyde-to-primary-alcohol template.