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Reactions of Carboxylic Acids

Decarboxylation of Carboxylic Acids

Specific carboxylic acids eliminate carbon dioxide relatively easily. That is, they decarboxylate. Examples of such carboxylic acids are β-keto acids and 1,3-dicarboxylic acids. The decarboxylation of these compounds is promoted by tautomerism and mesomerism, respectively. Oftentimes, decarboxylation occurs even at room temperature. As the α hydrogen atom is considerably acidic due to the effect of two adjacent carbonyl groups and the second carbonyl group may be easily removed through decarboxylation, these reactions are important in several ketone and carboxylic acid syntheses.

Fig.1
Decarboxylations
Fig.2
Four examples of carboxylic acids that easily decarboxylate
Fig.3

Malonic acid

Acetic acid

Fig.4

Starting material 1

Product 1

Fig.5

Starting material 2

Product 2

Fig.6

Starting material 3

Product 3

Exercises

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