Chapter 20, Problem 20.69P

An unknown compound A (molecular formula ${\text{C}}_{\text{7}}{\text{H}}_{\text{14}}\text{O}$) was treated with ${\text{NaBH}}_{\text{4}}$

in ${\text{CH}}_3\text{OH}$ to form compound B (molecular formula ${\text{C}}_{\text{7}}{\text{H}}_{\text{16}}\text{O}$). Compound A has a strong absorption in its IR spectrum at $171{\text{6 cm}}^{-1}$. Compound B has a strong absorption in its IR spectrum at $\text{3600}-3200{\text{ cm}}^{-1}$. The ${}^{\text{1}}\text{H}$ NMR spectra of A and B are given. What are the structures of A and B?