Return to Contents Chapter 14: Organometallic Compounds Ch 14 contents

Reactions of RC≡CM with Aldehydes and Ketones

addition of acetylides to aldehydes and ketones gives alcohols

Reaction usually in Et2O followed by H3O+ work-up

 


Reaction type:  Nucleophilic Addition

Summary

Related Reactions
NUCLEOPHILIC ADDITION OF RCCMgX 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 acetylenic 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