Chapter 9, Problem 28P

Compound Q has the molecular formula $C_7{H}_8$. The broad-band proton decoupled ${}^{13}C$ spectrum of Q has signals at $\text{δ}50$ (CH), $85\left(C{H}_2\right)$, and $144\left(CH\right)$. On catalytic hydrogenation Q is converted to R $\left(C_7{H}_{12}\right)$. Propose structures for Q and R.