Chapter 9, Problem 27P

Compound S $\left(C_8{H}_{16}\right)$ reacts with one mole of bromine to form a compound with molecular formula $C_8{H}_{16}B{r}_2$. The broadband proton-decoupled ${}^{13}C$ spectrum of S is given in Fig. 9.38. Propose a structure for S.

Figure 9.38 The broadband proton-decoupled ${}^{13}C$ NMR spectrum of compound S, Problem 9.27. Information from the DEPT ${}^{13}C$ NMR spectra is given above each peak.