An unknown compound gives the NMR, IR, and mass spectra shown next. Propose a structure, and show how it is consistent with the observed absorptions. Show fragmentations that account for the prominent ion at m z69 and the smaller peak at m>z 99.

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100 80 e 60 69 40 114M+ 20 10 ' 20 ' 30' 40 ' 50 ' 60 , 70 , 80 ' 90' 100' 110, 120, i30' 140, 150, 160 niz wavelength (um) 3.5 4 45 5 2.5 100 5 5.5 678 9 10 12 13 14 15 16 80 4000 3500 2000 1800 1600 1400 1200 1000 wavenumber (cm-) 200 180 160 140 120 100 80 60 40 20 0 S0Hz 5011z 50Hz 5.9δ 5.8δ 38 4.28 7.1ล 7.06 6.96 148 1.36 10 6 (ppm)