Chapter 9, Problem 42P

Deduce the structure of the compound that gives the following ${}^{1}H$, ${}^{13}C$, and IR spectra (Fig. 9.46-9.48). Assign all aspects of the ${}^{1}H$ and ${}^{13}C$ spectra to the structure you propose. Use letters to correlate protons with signals in the ${}^{1}H$ NMR spectrum, and numbers to correlate carbons with signals in the ${}^{13}C$ spectrum. The mass spectrum of this compound shows the molecular ion at m/z 204.

Figure 9.46 The ${}^{1}H$ NMR spectrum (simulated) for Problem 9.42.

Figure 9.47 A simulated broadband proton-decoupled ${}^{13}C$ NMR spectrum for Problem 9.42.

Figure 9.48 The IR spectrum for Problem 9.42. (SDBS, National Institute of Advanced Industrial Science and Technology)