A ketone C5H10O has three peaks in its carbon-13 NMR spectrum, one of them at δ 211. Is it pentan-2-one, pentan-3-one or 3-methylbutan-2-one?
- Pentan-2-one, CH3COCH2CH2CH3, has no symmetry: 5 environments, 5 peaks.
- 3-methylbutan-2-one, CH3COCH(CH3)2: the two CH3 groups on the CH are equivalent, giving 4 peaks.
- Pentan-3-one, CH3CH2COCH2CH3, is symmetrical about C=O: two CH3, two CH2 and one C=O give 3 peaks.
- The peak at δ 211 is the C=O carbon of a ketone (about 190–220).
Answer: Pentan-3-one