A short fragment of a polymer chain (two repeat units, end groups shown) is drawn. Which of the structures shown is the only organic product of its complete hydrolysis?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

The fragment is polycaprolactone, a biodegradable polyester. Each ester bond hydrolyses to a hydroxyl and a carboxyl group, so the only product is 6-hydroxyhexanoic acid. Caprolactone is the cyclic monomer, not a hydrolysis product, the diol has no acid group and adipic acid has the wrong oxidation pattern.

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