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13.17: Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

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JoVE Core
Organic Chemistry

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Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives
 
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13.17: Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.

Figure1

The mechanism initiates with an internal electronic redistribution, resulting in a cyclic six-membered transition state. This is followed by a C–C bond cleavage to produce an enol by releasing carbon dioxide gas. Next, the enol rapidly tautomerizes under the acidic conditions to yield a more stable monocarboxylic acid.

Figure2

In malonic ester synthesis, the key step is the decarboxylation of malonic acid, wherein alkyl halides are converted to monocarboxylic acids.

Figure3

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Keywords: Decarboxylation Malonic Acid Monocarboxylic Acid Keto Acid Dicarboxylic Acid Enol Tautomerization Malonic Ester Synthesis Carbon Dioxide

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