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The loss of carbon dioxide from a carboxylic acid is called decarboxylation. Although decarboxylation is not an important reaction for most ordinary carboxylic acids, certain types of carboxylic acid are readily decarboxylated. Among these are
1. beta-keto acids
2. malonic acid derivatives
3. carbonic acid derivatives and many other types mentioned in this video by MKA Sir.
Beta-Keto acids-carboxylic acids with a keto group in the b-position-readily decarboxylate at room temperature in an acidic solution.
Decarboxylation of a beta-keto acid involves an enol intermediate that is formed by an internal proton transfer from the carboxylic acid group to the carbonyl oxygen atom of the ketone.
The enol is transformed spontaneously into the corresponding ketone.
The acid form of the beta-keto acid decarboxylates more readily than the conjugate-base carboxylate form because the latter has no acidic proton that can be donated to the b-carbonyl
oxygen. In effect, the carboxy group promotes its own removal!
Malonic acid and its derivatives readily decarboxylate upon heating in an acidic solution.
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