Return to Contents Chapter 14: Organometallic Compounds Ch 14 contents

Reactivity of Organometallics
As we have seen previously, the carbon attached to the metal is anionic in character, so it reacts as a carbanion, a nucleophilic carbon.

In principle there are 3 important groups of reactions where nucleophiles attack electrophilic C atoms.
For the organometallic reagents these types of reactions will result in the formation of new C-C bonds.
Limitations will be discussed below.
 

General Mechanism Organometallic Application
1. Nucleophilic Substitution  Chapter 8
Nucleophilic substitution at sp3 C R2CuLi with alkyl halides or tosylates to give alkanes
2. Nucleophilic Addition   Chapter 17
Nucleophilic addition to aldehydes and ketones RLi or RMgX with aldehydes or ketones to give 2o or 3o alcohols
3. Nucleophilic Acyl Substitution  Chapter 20
Nucleophilic acyl substitution of carboxylic acid derivatives RLi or RMgX with esters to give 3o alcohols
Study Tip:
Note that the electrophilic C atoms can be recognised by realising that they are connected to electronegative atoms (esp. halides or oxygen).

Limitations:


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© Dr. Ian Hunt, Department of Chemistry, University of Calgary