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Organometallic Reagents

A carbon bonded to a metal, of much lower electronegativity, becomes an electron-rich centre and hence a nucleophile. The C-Metal bond is very polar.

Polarization of the carbon–metal bond: the carbon bears a negative charge

Organometallic compounds are prepared by treating a halogenated derivative with a metal. The most common ones are those of lithium and magnesium. Organomagnesium compounds are called Grignard reagents.

Portrait of Victor Grignard

Victor Grignard (1871-1935): French chemist. In 1900 he discovered the organomagnesium reagents that bear his name. This discovery earned him the 1912 Nobel Prize in Chemistry, shared with Sabatier. He was the author of a 20-volume treatise on organic chemistry.

Preparation of organolithium and organomagnesium (Grignard) reagents from alkyl bromides

Organometallics have to be used right after their preparation because they are so reactive that they are quickly and violently destroyed by oxygen and moisture. Their preparation and use must be carried out under inert atmosphere (N2 or Ar).

Organometallics are very strong bases (alkane pKa > 50) and react violently with water

Organometallic reagents are very good carbon nucleophiles and are used to build new C-C bonds, the most important task in Organic Chemistry. Here are some examples:

Synthesis of primary, secondary and tertiary alcohols by addition of organometallics to formaldehyde, aldehydes and ketones