Compounds that contain a metal-carbon bond, R-M, are known as "organometallic" compounds.
Organometallic compounds of Li, Mg (Grignard reagents) are amongst some of the most important organic reagents.
Many other metals have been utilized, for example Na, Cu and Zn.

Organometallic compounds provide a source of nucleophilic carbon atoms which react with electrophilic carbon and so form a new carbon-carbon bond.  This is very important for the synthesis of complex molecules from simple starting materials.

To rationalize the general reactivity of organometallics it is convenient to view them as ionic, so R-M  =  R^- M⁺

The most important reactions is this chapter are the reactions of organolithiums, RLi, and Grignard reagents, RMgX, with the carbonyl groups in aldehydes, ketones and esters to give alcohols. However we will also look at some useful reactions involving Cu, Zn and Hg (mercury).

Organometallic Compounds

• Nomenclature
• Structure
• Reactivity
• Basicity

• Organolithiums RLi
• Organomagnesium or Grignards, RMgX
• Dialkyllithium cuprates, R₂CuLi
• Organozinc reagents, RZnX
• Acetylides, RCºCM

• Overview of Reactions
• Overview of Grignard Reactions
• Addition of RLi and RMgX to Aldehydes and Ketones
• Addition of RCºCM to Aldehydes and Ketones
• Addition of RLi and RMgX to Esters
• Alkane synthesis using R₂CuLi
• Reactions of RZnX
• Oxymercuration-Demercuration of Alkenes

• How to Plan a Synthesis

• Self Assessment

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