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The compound shown gives four 1H NMR signals. Select all of the structures shown that give fewer than four signals. Chemically equivalent hydrogens give one signal; ignore coupling and axial/equatorial differences.

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: A, D

Toluene (shown) has 4 sets. A (o-xylene) has , two kinds of ring H: 3. B (m-xylene) has CH3, H2, H4/H6, H5: 4. C (4-methylanisole) has , and two ring sets: 4. D (propanal) has , , : 3.
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