Decarboxylation

Decarboxylation is a chemical reaction that removes a carboxyl group from a molecule, usually releasing carbon dioxide. It occurs in organic synthesis and in many metabolic pathways.

Carboxyl group: A carbon atom bonded to oxygen by a double bond and to a hydroxyl group. Decarboxylation removes this functional group from a molecule.
Carboxylic acid: An organic compound containing one or more carboxyl groups. Many decarboxylation substrates are carboxylic acids or their derivatives.
Kolbe electrolysis: An electrochemical reaction in which carboxylate ions lose carbon dioxide and couple to form carbon–carbon bonds. It uses decarboxylation to build larger organic molecules.
Decarbonylation: A reaction that removes carbon monoxide from a molecule. It removes a carbon-containing group but releases carbon monoxide rather than carbon dioxide.
Malonic ester synthesis: A carbon–carbon bond-forming method that alkylates a malonic ester and then hydrolyzes and decarboxylates it. The final decarboxylation yields a substituted carboxylic acid.
β-Keto acid: A carboxylic acid with a ketone group on the carbon adjacent to its carboxyl group. Its arrangement allows carbon dioxide loss through a favorable cyclic transition state.
Carbon–carbon bond: A covalent bond joining two carbon atoms. Removing a carboxyl group breaks a bond between its carbon and the molecular residue.
Hunsdiecker reaction: A reaction that converts a silver carboxylate into an alkyl halide with loss of carbon dioxide. It turns decarboxylation into a method for shortening a carbon chain.
Dehydration reaction: A reaction that removes water from a molecule, often forming a double bond. It is another elimination reaction, but removes water instead of a carboxyl group.
Acetoacetic ester synthesis: A method for preparing substituted methyl ketones through alkylation, hydrolysis, and decarboxylation of ethyl acetoacetate. Decarboxylation completes the synthesis by converting a β-keto acid into a ketone.

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