Chapter 9, Problem 41P

Deduce the structure of the compound that gives the following ${}^{1}H$, ${}^{13}C$, and IR spectra (Fig. 9.43-9.45). Assign all aspects of the ${}^{1}H$ and ${}^{13}C$ spectra to the structure you propose. Use letters to correlate protons with the signals in the ${}^{1}H$ NMR spectrum, and numbers to correlate carbons with the signals in the ${}^{13}C$ spectrum. The mass spectrum of this compound shows the molecular ion at m/z 148.

Figure 9.43 The ${}^{1}H$ NMR spectrum (simulated) for Problem 9.41.

Figure 9.44 A simulated broadband proton-decoupled ${}^{13}C$ NMR spectrum for Problem 9.41. Information from the DEPT ${}^{13}C$ spectra is given above each peak.

Figure 9.45 The IR spectrum for Problem 9.41. (SDBS, National Institute of Advanced Industrial Science and Technology)