|Chapter 14: Organometallic Compounds|
Reactions of RLi and RMgX with Aldehydes and Ketones
Reactions usually in Et2O or THF followed by H3O+ work-ups
Reaction type: Nucleophilic Addition
NUCLEOPHILIC ADDITION OF RLi or RMgX TO AN ALDEHYDE
The nucleophilic C in the organometallic reagent adds to the electrophilic C in the polar carbonyl group, electrons from the C=O move to the electronegative O creating an intermediate metal alkoxide complex.
This is the work-up step, a simple acid/base reaction. Protonation of the alkoxide oxygen creates the alcohol product from the intermediate complex.
|© Dr. Ian Hunt, Department of Chemistry|