Chapter SRP, Problem 35P

A compound X $\left({\text{C}}_{\text{10}}{\text{H}}_{\text{14}}\text{O}\right)$ dissolves in aqueous sodium hydroxide but is insoluble in aqueous sodium bicarbonate. Compound X reacts with bromine in water to yield a dibromo derivative, ${\text{C}}_{\text{10}}{\text{H}}_{\text{12}}{\text{Br}}_{\text{2}}\text{O}$. The 3000–4000 ${\text{cm}}^{-1}$ region of the IR spectrum of X shows a broad peak centered at 3250 ${\text{cm}}^{-1}$; the 680–840 ${\text{cm}}^{-1}$ region shows a strong peak at 830 ${\text{cm}}^{-1}$. The ${}^{\text{1}}\text{H NMR}$ spectrum of X gives the following: singlet at $\delta$ 1.3 (9H), singlet at $\delta$ 4.9 (1H), and multiplet at $\delta$ 7.0 (4H). What is the structure of X?