Return to Contents  Chapter 17: Aldehydes and Ketones. Nucleophilic Addition to C=O  Ch 17 contents

Reactions of RLi and RMgX with Aldehydes and Ketones
(review of Chapter 14)

reaction of RLi or RMgX with aldehydes and ketones
Reactions usually in Et2O or THF followed by H3O+ work-ups

Reaction type:  Nucleophilic Addition

Summary

Related Reactions
NUCLEOPHILIC ADDITION OF RLi or RMgX TO AN ALDEHYDE
Step 1:
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.
addition of Grignard reagent to an aldehyde
Step 2:
This is the  work-up step, a simple acid / base reaction. Protonation of the alkoxide oxygen creates the alcohol product from the intermediate complex.

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