Chapter 20, Problem 20.73P

Treatment of compound C (molecular formula ${\text{C}}_4{\text{H}}_8\text{O}$) with ${\text{C}}_6{\text{H}}_{\text{5}}\text{MgBr}$, followed by ${\text{H}}_{\text{2}}\text{O}$, affords compound D (molecular formula ${\text{C}}_{10}{\text{H}}_{14}\text{O}$). Compound D has a strong peak in its IR spectrum at $3600-320{\text{0 cm}}^{-1}$. The ${}^1\text{H}$ NMR spectrum data of C and D are given. What are the structures of C and D?

Compound C signals at $1.3\left(\text{singlet, 6H}\right)$ and $2.4\left(\text{singlet, 2H}\right)\text{ppm}$.

Compound D signals at $1.2\left(\text{singlet, 6H}\right)\text{, 1}\text{.6}\left(\text{singlet, 1H}\right),\text{ 2}\text{.7}\left(\text{singlet, 2H}\right)$ and $7.2\left(\text{multiplet, 5H}\right)\text{ppm}$.