Chapter SRP, Problem 34P

Compound C $\left({\text{C}}_{\text{9}}{\text{H}}_{\text{11}}\text{NO}\right)$ gives a positive Tollens’ test (can be oxidized to a carboxylic acid, Sect. 16.13B) and is soluble in dilute HCl. The IR spectrum of C shows a strong band near 1695 cm^−-1 but shows no bands in the 3300–3500 cm^−-1 region. The broadband proton-decoupled ${}^{13}\text{C NMR}$ spectrum of C is shown in Fig. 5. Propose a structure for C.

Figure 5 The broadband proton-decoupled ${}^{13}\text{C NMR}$ spectra of compound C, Problem 34. Information from the DEPT ${}^{13}\text{C NMR}$ spectra is given above each peak.