A short fragment of a polymer chain (one amide link, end groups shown) is drawn. On complete acid hydrolysis of the amide, which pair of compounds, shown as two molecules among the structures, is obtained (ignoring salt formation)?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B

The fragment is a piece of nylon 6,6. Hydrolysis cleaves the C-N bond of the amide, giving an amine and a carboxylic acid: hexane-1,6-diamine and hexanedioic acid. An alcohol or diol would need an ester, and a different diacid would change the carbon count.

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