Grignard reagent

A Grignard reagent is an organomagnesium compound with the formula R–Mg–X. It acts as a carbon nucleophile in reactions that form carbon–carbon bonds.

Carbon–magnesium bond: A bond between carbon and magnesium with substantial polarization toward carbon. Its polarization gives the carbon in a Grignard reagent nucleophilic character.
Organometallic chemistry: The study of compounds containing bonds between carbon and metals. Grignard reagents are a foundational class of carbon–metal compounds.
Alcohol: An organic compound containing a hydroxyl group bonded to a saturated carbon atom. Workup of Grignard addition to carbonyl compounds commonly produces alcohols.
Gilman reagent: An organocuprate, commonly R₂CuLi, used in carbon–carbon bond-forming reactions. Gilman reagents are less reactive than Grignard reagents and can favor conjugate addition.
Victor Grignard: A French chemist whose organomagnesium research earned the 1912 Nobel Prize in Chemistry. His work introduced the reagents that now bear his name.
Nucleophilic addition: A reaction in which a nucleophile adds to an electrophilic multiple bond. Grignard reagents add to carbonyl groups through this reaction pattern.
Alkyl halide: An organic compound in which a halogen is bonded to an sp³-hybridized carbon atom. Alkyl halides commonly supply the carbon and halogen used to prepare Grignard reagents.
Tertiary alcohol: An alcohol whose hydroxyl-bearing carbon is bonded to three other carbon atoms. Addition to a ketone is a standard route from a Grignard reagent to a tertiary alcohol.
Enolate: A resonance-stabilized anion formed by deprotonation of a carbonyl compound at its alpha carbon. Enolates are carbon nucleophiles generated from carbonyl compounds, unlike magnesium-bound carbon nucleophiles.
François Auguste Victor Grignard: The full name of French chemist Victor Grignard. This alternate name identifies the same chemist; it is not a separate historical figure.

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