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The molecules A and B are a pair of ____________.

Two fused polycyclic structures A and B, each with a 4-nitrophenyl group on an sp3 CH, a dimethylcyclohexenone ring and a julolidine-type N; in A the CH bearing the aryl group is bonded to N, in B it is bonded to the benzo ring carbon.

  • A.enantiomers
  • B.diastereomers
  • C.conformational isomers
  • D.constitutional isomers

Answer: D

A and B are constitutional isomers.

They have the same molecular formula but different connectivity. In A the sp3 carbon carrying the 4-nitrophenyl group is bonded to the ring nitrogen, and the C=C bond joins the benzo-ring carbon to the enone carbon. In B the sp3 carbon carrying the aryl group is bonded to the benzo-ring carbon instead, and the C=C bond now joins the carbon next to nitrogen to the enone carbon.

Because atoms are joined differently, they cannot be enantiomers or diastereomers, which share connectivity and differ only in spatial arrangement, and they cannot be conformers, which interconvert by bond rotation. B is drawn flipped and with a hashed bond to make it look like a mirror image of A, which is the trap.

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