A short fragment of the polymer chain (two repeat units, end groups shown) is drawn. Which cyclic compound, among the structures shown, is the usual industrial monomer that polymerises by ring opening to give this polymer?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B

The repeat unit -NH-(CH2)5-CO- is nylon 6. It is made by heating caprolactam (azepan-2-one, a seven-membered lactam) with a little water, which opens the ring and links the units by amide bonds. Cyclohexanone oxime is only a precursor of caprolactam, caprolactone would give a polyester and delta-valerolactam would give nylon 5.

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