Treatment of compound D with LIAIH4 followed by H20 forms compound E. D shows a molecular...

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Treatment of compound D with LIAIH4 followed by H20 forms compound E. D shows a molecular ion in its mass spectrum at m/z 71 and IR absorptions at 3600 - 3200 and 2263 cm-1. E shows a molecular ion in its mass spectrum at m/z 75 and IR absorptions at 3636 and 3600 - 3200 cm-1. Propose structures for D and E from these data and the given 'H NMR spectra. 1H NMR of D 2H 2H 1H 8 7 6 5 4 3 2 ppm Treatment of compound D with LIAIH4 followed by H20 forms compound E. D shows a molecular ion in its mass spectrum at m/z 71 and IR absorptions at 3600 - 3200 and 2263 cm-1. E shows a molecular ion in its mass spectrum at m/z 75 and IR absorptions at 3636 and 3600 - 3200 cm-1. Propose structures for D and E from these data and the given 'H NMR spectra. 1H NMR of D 2H 2H 1H 8 7 6 5 4 3 2 ppm