Help with Other Carbonyl Products - Organic Chemistry

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Question

When butanoic acid undergoes the Hell-Volhard-Zelinsky (HVZ) reaction, the final product is                     .

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Answer

In the HVZ reaction of a carboxylic acid, a bromine is added to the alpha carbon. Phosphorus catalyzes the reaction and allows for the formation of an acyl halide. Acyl halides readily undergo enol-ketone tautomerization. The enol form uses electrons from the carbon-carbon double bond to bond to the bromine. In water, the two bromine molecules convert back to a carboxylic acid with one bromine on the alpha carbon.

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