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 Chapter 18: Enols and Enolates 
Ch 18 contents

Basic α-Halogenation of Aldehydes and Ketones

Reaction type : Nucleophilic substitution

Summary

Related Reactions
MECHANISM OF α-HALOGENATION OF ALDEHYDES AND KETONES UNDER BASIC CONDITIONS
Step 1:
First, an acid-base reaction. Hydroxide functions as a base and removes the acidic α-hydrogen giving the enolate.
mechanism of basic halogenation of aldehydes and ketones
Step 2:
The nucleophilic enolate reacts with the halide giving the halogenated ketone and a bromide ion.
 

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