Chapter 20, Problem 47P

Compound $A\left(C_{10}{H}_{15}N\right)$ is soluble in dilute HCI. The IR absorption spectrum shows two bands in the $3300-3500c{m}^{-1}$ region. The broadband proton-decoupled ${}^{13}C$ spectrum of A is given in Fig. 20.8. Propose a structure for A.

FIGURE 20.8 The broadband proton-decoupled ${}^{13}C$ NMR spectra of compounds A and B, Problems 20.47 and 20.48. Information from the DEPT ${}^{13}C$ NMR spectra is given above each peak.