Treatment of compound D with LIAIH4 followed by H2O 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. 'H NMR of D 2H 2H 1H 8 7 6 2 ppm

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Treatment of compound D with LIAIH4
followed by H2O 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.
'H NMR of D
2H
2H
1H
8
7
6
2
ppm
Transcribed Image Text:Treatment of compound D with LIAIH4 followed by H2O 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. 'H NMR of D 2H 2H 1H 8 7 6 2 ppm
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