A chemist, Ilov Boronin, carried out a reaction of frans-2-pentene with BH3 in THF followed by treatment with H2O2/-OH. Two products were separated and isolated. Desperate to know their structures, Ilov took his compounds to the spectroscopy laboratory and found that only the mass spectrometer was operating. The mass spectra of the two products are given in Fig. P12.37. Suggest structures for the compounds, and indicate which mass spectrum goes with which compound.
Fig. P12.37

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45 80 2 20 0 10 20 30 450 60 7 80 90 100 110 120 130 140 mass-to-charge ratio m/z 100 80 60 40 59 0 0 0 20 30 40 50 60 70 80 90 100 0 120 30 140 mass-to-charge ratio m/a 2