Cyanohydrin formation
Cyanide addition to a ketone forms a hydroxynitrile, adding a second carbonyl route into the expanded organic network.
- Reagents
- HCN with KCN catalyst
- Conditions
- room temperature
- Reaction class
- nucleophilic addition
- Equation
- R-CO-R' + HCN -> R-C(OH)(CN)-R'
Overview
Cyanide addition to a ketone forms a hydroxynitrile, adding a second carbonyl route into the expanded organic network.
Transformation
- Equation
- R-CO-R' + HCN -> R-C(OH)(CN)-R'
- Reagents
- HCN with KCN catalyst
- Environment
- room temperature
- Reaction class
- nucleophilic addition
- Mechanism
- nucleophilic addition
- Evidence level
- textbook core
Scope and limitations
- Scope
- Ketones react with cyanide / hydrogen cyanide to form substituted hydroxynitriles.
- Limitations
- This route records the addition outcome; ketone cyanohydrins can contain two carbon substituents at the alcohol-bearing carbon.
Related reactions
- Cyanohydrin formation: Aldehydes → Hydroxynitriles
Cyanide addition to an aldehyde forms a hydroxynitrile, giving a carbonyl-route analogue of the nitrile chain-extension motif.
- Oxidation: Alcohols → Ketones
Oxidation of a secondary alcohol gives a ketone.
- Oxidation: Secondary alcohols → Ketones
Oxidation of a secondary alcohol gives a ketone.
- Reduction: Ketones → Secondary alcohols
Reduction of a ketone gives a secondary alcohol.
- Grignard addition co reactant: Ketones → Tertiary alcohols
Ketones plus Grignard reagents give tertiary alcohols after acidic work-up.
References
- Organic Chemistry: Nucleophilic Addition of HCN: Cyanohydrin FormationJohn McMurry · OpenStax Organic Chemistry · 2023
Supports cyanide addition to aldehydes and unhindered ketones followed by protonation to form cyanohydrins / hydroxynitriles.