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.

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.

CH A, CgH1BO CH2 CH CDCl3 TMS 220 200 180 60 140 20 100 80 60 40 20 oc (ppm)

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