An unknown compound shows a weak molecular ion at m/z87 in the mass spectrum, and the only large peak is at m/z30. The IR spectrum follows. The NMR spectrum shows only three singlets: one of area 9 at δ 0.9, one of area 2 at δ 1.0, and one of area 2 at δ 2.4. The singlet at δ 1.0 disappears on shaking with D₂O. Determine the structure of the compound, and show the favorable fragmentation that accounts for the ion at m/z 30.

Transcribed Image Text:

wavelength (um) 5.5 2.5 3.5 4 4.5 7 8 9 10 11 12 13 14 15 16 100 80 60 40 20 4000 3500 3000 2500 2000 1800 1600 1400 1200 1000 800 600 wavenumber (cm) TRANSMITTANC