Grignard addition co reactant
Ketones plus Grignard reagents give tertiary alcohols after acidic work-up.
- Reagents
- Grignard reagent, then dilute acid
- Conditions
- dry ether, then acidic work-up
- Reaction class
- nucleophilic addition
- Equation
- R'COR'' + R-MgX -> R'C(OMgX)(R)R''; then H3O+ -> R'C(OH)(R)R''
Overview
Ketones plus Grignard reagents give tertiary alcohols after acidic work-up.
Transformation
- Equation
- R'COR'' + R-MgX -> R'C(OMgX)(R)R''; then H3O+ -> R'C(OH)(R)R''
- Reagents
- Grignard reagent, then dilute acid
- Environment
- dry ether, then acidic work-up
- Reaction class
- nucleophilic addition
- Mechanism
- Grignard carbonyl addition
- Evidence level
- textbook core
Scope and limitations
- Scope
- Ketones are carbonyl co-reactants that give tertiary alcohols after Grignard addition and acidic work-up.
- Limitations
- This record represents the ketone co-reactant branch of Grignard addition and points to the same tertiary-alcohol outcome.
Related reactions
- Cyanohydrin formation: Ketones → Hydroxynitriles
Cyanide addition to a ketone forms a hydroxynitrile, adding a second carbonyl route into the expanded organic network.
- 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.
- Carbonyl addition: Grignard reagents → Tertiary alcohols
Grignard addition to ketones gives tertiary alcohols after work-up.
References
- Organic Chemistry: Nucleophilic Addition of Hydride and Grignard ReagentsJohn McMurry · OpenStax Organic Chemistry · 2023
Supports Grignard carbon nucleophiles adding to aldehydes and ketones to give alkoxide intermediates, followed by protonation during acidic work-up.