An unknown compound with molecular formula C9H180 forms a phenylhydrazone, but gives a negative with Tollens' test. The IR spectrum has a strong band near 1710 cm. The broadband proton- decoupled "C NMR spectrum is given below. Propose a structure for the unknown compound. Explain your answer based on the given spectroscopic data CH3 A, C3H180 CH2 CH CDCI3 TMS C 220 200 180 160 140 120 100 80 60 40 20 S (ppm)

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An unknown compound with molecular formula C9H180 forms a phenylhydrazone, but gives a
negative with Tollens' test. The IR spectrum has a strong band near 1710 cm. The broadband proton-
decoupled "C NMR spectrum is given below. Propose a structure for the unknown compound. Explain
your answer based on the given spectroscopic data
CH3
A, C3H180
CH2
CH
CDCI3
TMS
220
200
180
160
140
120
100
80
60
40
20
S, (ppm)
Transcribed Image Text:An unknown compound with molecular formula C9H180 forms a phenylhydrazone, but gives a negative with Tollens' test. The IR spectrum has a strong band near 1710 cm. The broadband proton- decoupled "C NMR spectrum is given below. Propose a structure for the unknown compound. Explain your answer based on the given spectroscopic data CH3 A, C3H180 CH2 CH CDCI3 TMS 220 200 180 160 140 120 100 80 60 40 20 S, (ppm)
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