Chapter SRP, Problem 36P

Compound Z $\left({\text{C}}_{\text{5}}{\text{H}}_{\text{10}}\text{O}\right)$ decolorizes bromine. The IR spectrum of Z shows a broad peak in the 3200–3600 cm^−-1 region. The ${}^1\text{H NMR}$ 1H NMR spectrum of Z is given in Fig. 6. Propose a structure for Z.

Figure 6 The ${}^1\text{H NMR}$ spectrum of compound Z (Problem 36). Expansions of the signals are shown in the offset plots.