Chapter 23, Problem 23.69P

Treatment of W with ${\text{CH}}_{\text{3}}\text{Li}$, followed by ${\text{CH}}_{\text{3}}\text{I}$, affords compound Y $\left({\text{C}}_{\text{7}}{\text{H}}_{\text{14}}\text{O}\right)$ as the major product. Y shows a strong absorption in its IR spectrum at $\text{1713}{\text{cm}}^{-1}$, and its ${}^{\text{1}}\text{H}$ NMR spectrum is given below. (a) Propose a structure f or Y. (b) Draw a stepwise mechanism f or the conversion of W to Y.