carbon chain reaction

Carboxylic acid and ester can combine to make longer carbon chain {carbon chain reaction}, if negatively charged nucleophile is present. Negatively charged nucleophile can create carbanion on carboxylic-acid second carbon. Carbanion can attack ester. Negative charge migrates to ester double-bonded oxygen. First ester carbon bonds to first carboxyl carbon. Carboxyl reforms as nucleophile leaves, leaving new carbon-carbon single bond.

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