|Chapter 14: Organometallic Compounds|
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|
|R2CuLi with alkyl halides or tosylates to give alkanes|
|2. Nucleophilic Addition Chapter 17|
|RLi or RMgX with aldehydes or ketones to give 2o or 3o alcohols|
|3. Nucleophilic Acyl Substitution Chapter 20|
|RLi or RMgX with esters to give 3o alcohols|
Note that the electrophilic C atoms can be recognised by realising that they are connected to electronegative atoms (esp. halides or oxygen).
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|