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What is a diastereotopic pair of protons?

  • A.Two protons on one carbon that are not equivalent
  • B.Two protons on adjacent carbons that couple strongly
  • C.Two protons that exchange rapidly with the solvent
  • D.Two protons whose shifts happen to coincide by chance

Answer: A

When a molecule contains a stereocentre, the two protons of a nearby methylene sit in different environments and have different chemical shifts and couple to each other, giving an AB pattern rather than a singlet. It is a frequent puzzle in the spectra of chiral compounds and a strong clue that a stereocentre is present. Vicinal coupling, exchange and accidental coincidence are all different situations. Replacing each proton in turn and asking whether the products are diastereomers is the formal test.

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