Draw the structures of the four isomeric alcohols with molecular formula C4H9OH.
(a) Which isomer has the 13C NMR spectrum shown in Figure 12.14? Explain why.
(b) Two of the four isomers will have the same number of peaks (4) in their decoupled 13C NMR spectra. What are their structures? How could a 13C-1H coupled spectrum be used to distinguish between them?

Figure 12.14
13C NMR spectrum.

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TMS CDCI 180 170 160 150 140 130 120 10 100 90 80 70 60 50 40 3 20 10 0 δ (ppm)