Question: An unknown compound gives a mass spectrum with a weak molecular ion at m/z 113 and a prominent ion at m z 68. Its NMR

An unknown compound gives a mass spectrum with a weak molecular ion at m/z 113 and a prominent ion at m z 68. Its NMR and IR spectra are shown here. Determine the structure, and show how it is consistent with the observed absorptions. Propose a favorable fragmentation to explain the prominent MS peak at m/z 68.

wavelength (um 5 5.5 6 2.5 100 4 4.5 7 8 9 10 12 13 14 15 16 60 N 40111 4000 3000 2500 2000 1800 1600 1400 1200 1000 800 600 wavenumber (cm) 200 180 160 140 120 100 80 60 40 20 10 0 (ppm)

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