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13.16: Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

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JoVE Core
Organic Chemistry

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Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids
 
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13.16: Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.

Figure1

Unlike monocarboxylic acids, ꞵ-keto acids bearing a keto group at the β position to the carboxyl group, readily undergo decarboxylation under an acid medium to form a ketone and releases carbon dioxide gas.

Figure2

Decarboxylation reaction is biologically relevant while oxidizing food materials in the tricarboxylic acid (TCA) cycle. In this cycle, oxalosuccinic acid is formed as an intermediate that bears three carboxyl groups and one carbonyl group. However, as the carbonyl group is at the ꞵ-position to only one carboxyl group, only one of the three carboxyl groups undergoes decarboxylation to produce α-ketoglutaric acid by losing CO2.

Figure3

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Keywords: Decarboxylation β-ketoacids Carboxylic Acids Hunsdiecker Reaction TCA Cycle Oxalosuccinic Acid α-ketoglutaric Acid Carbon Dioxide Ketone Oxidation

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