The following spectra for A and B correspond to two structural isomers. The NMR singlet at (1.16 in spectrum A disappears when the sample is shaken with D2O.The singlet at (0.6 ppm in the spectrum of B disappears on shaking with D2O. Propose structures for these isomers, and show how your structures correspond to the spectra. Show what cleavage is responsible for the base peak at m / z 44 in the mass spectrum of A and the prominent peak at m / z 58 in the mass spectrum of B.

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100 60 a 40 73 1 0 20 30 40 5O 60 D0 80 90 100110 120 130 140 50 160 wavelength (um) 5 5.5 6 2.5 100 3.5 4 4.5 8 9 10 12 13 14 15 16 2000 1 1800 600 400 1200 1000 800 600 wavenumber(cm 200 180 160 140 120 100 80 60 40 20 10 5 100 80 60 E 40 M' 73 20 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 mに wavelength yan 5 55 6 3.5 2.5 100 4 4.5 4000 3500 3000 2500 2000 1800 1600 1400 200 1000 800 600 wavenumber (cm 10 δ ippm)