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15.8: Base-Promoted α-Halogenation of Aldehydes and Ketones

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Organic Chemistry

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Base-Promoted α-Halogenation of Aldehydes and Ketones

15.8: Base-Promoted α-Halogenation of Aldehydes and Ketones

α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction at the stage of monosubstitution. This is due to  the electron withdrawing inductive effect of the halogen that makes the remaining hydrogens highly acidic. As a consequence, the monohalogentaed compound undergoes further rapid enolization and halogenation until all α hydrogens are replaced by halogens.


Base-promoted α-halogenation Aldehydes Ketones Substitution α Hydrogens Halogens Base Nucleophilic Enolate Ion Monohalogenated Carbonyl Compound Electron Withdrawing Inductive Effect Acidic Enolization Rapid Halogenation

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