Chapter 25, Problem 25.85P

Treatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its mass spectrum at $m\text{/}z=71$ and IR absorptions at $3600-3200$ and ${\text{2263 cm}}^{-1}$. E shows a molecular ion in its mass spectrum at $m\text{/}z=75$ and IR absorptions at $3636$ and $3600-{\text{3200 cm}}^{-1}$. Propose structures for D and E from these data and the given H NMR spectra.