Chapter 14, Problem 14.72P

When $2$-bromo- $3,3$-dimethylbutane is treated with ${\text{K}}^{+}{}^{-}\text{OC}{\left({\text{CH}}_{\text{3}}\right)}_{\text{3}}$, a single product T having molecular formula ${\text{C}}_{\text{6}}{\text{H}}_{\text{12}}$ is formed. When $3,3$-dimethylbutan- $2$-ol is treated with ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$, the major product U has the same molecular formula. Given the following ${}^1\text{H NMR}$ data, what are the structures of T and U? Explain in detail the splitting patterns observed for the three split signals in T.

${}^1\text{H NMR}$ of T: $\text{1}\text{.01}\left(\text{singlet}9\text{H}\right)$, $4.\text{82}\left(\text{doublet of doublets,}1\text{H, }J=10,1.7\text{Hz}\right)$, $4.\text{93}\left(\text{doublet of doublets,}1\text{H, }J=18,1.7\text{Hz}\right)$ 4.93, and $\text{5}\text{.83}\left(\text{doublet of doublets,}1\text{H, }J=18,10\text{Hz}\right)\text{ppm}$

${}^1\text{H NMR}$ of U: $\text{1}\text{.60}\left(\text{singlet}\right)\text{ppm}$