Organomagnesium carbon nucleophiles
An organomagnesium reagent can transfer its carbon group to an aldehyde or ketone carbonyl, forming an alkoxide and a new carbon–carbon bond.
Key knowledge
An organomagnesium reagent can transfer its carbon group to an aldehyde or ketone carbonyl, forming an alkoxide and a new carbon–carbon bond. Protonation gives an alcohol. Formaldehyde, other aldehydes and ketones produce primary, secondary and tertiary alcohols respectively in the simple addition model.
Conditions and scope
- Water and acidic functional groups consume strongly basic organomagnesium species.
- Other electrophilic groups and substrate geometry can alter selectivity; the carbon is a nucleophilic equivalent rather than an isolated free carbanion.
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Evidence and review
Read formaldehyde/aldehyde/ketone products, acid quenching and incompatible functionality; omitted newer special acid-activation chemistry.
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Entry details
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- uni-chem-grignard-carbon-bond
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- core.1
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- University core expansion