Hell-Volhard-Zelinsky reaction

The Hell-Volhard-Zelinsky reaction is an organic reaction used to convert a carboxylic acid with an α-hydrogen and a halogen, to an α-halo carboxylic acid, using a phosphorous catalyst and water. The mechanism begins with the reaction of the carbonyl oxygen with phosphorous trihalide to form a P–O bond and release a halide anion. The halide then attacks the carbonyl to form an intermediate which rearranges to release an acyl chloride, an acid molecule, and a phosphine oxide. The acyl chloride then tautomerizes to the enol form which subsequently attacks the halogen molecule to form an α-halo acyl halide. Water hydrolysis yields the final α-halo carboxylic acid product.^[1][2][3]