An unknown compound of molecular formula C5H9NO gives the IR and NMR spectra shown here. The broad NMR peak at δ7.55 disappears when the sample is shaken with D2O. Propose a structure, and show how it is consistent with the absorptions in the spectra.

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wavelength (um) 5 5.5 6 4 4.5 100 60 N 40 I 4000 3500 3000 2500 2000 1800 1600 1400 1200 1000 wavenumber (cm 200 180 160 140 120 100 80 60 40 20 0 10 0 δ (ppm)