Making α-Haloacids from Carboxylic Acids

Making α-haloacids from carboxylic acids requires steps that differ from the usual halogenation of aldehydes and ketones. Carboxylic acids do not readily take part in α halogenation through enols or enolate intermediates. Instead, chemists use other routes to install a halogen on the α carbon.

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Unlike α-halogenation of aldehydes and ketones that occurs through enol or enolate intermediates, carboxylic acids and their derivatives do not readily undergo such reactions due to inadequate enolization.

This is because such molecules, under basic conditions, undergo deprotonation of the more acidic hydrogen, thereby inhibiting enolate ...