Compound A (C9H18O) forms a phenylhydrazone, but it gives a negative Tollens' test. The IR spectrum of

Question:

Compound A (C9H18O) forms a phenylhydrazone, but it gives a negative Tollens' test. The IR spectrum of A has a strong band near 1710 cm-1. The broadband proton decoupled 13C NMR spectrum of A is given in Fig. 16.6. Propose a structure for A.

Figure 16.6 T he broadband proton-decoupled 13C NMR spectrum of compound A, Problem 16.51. Information from the DEPT 13C NMR spectra is given above the peaks.