Chapter 21, Problem 32P

A compound X (C₁₀H₁₄O) dissolves in aqueous sodium hydroxide but is insoluble in aqueous sodium bicarbonate. Compound X reacts with bromine in water to yield a dibromo derivative, C₁₀H₁₂Br₂O. The 3000–4000-cm⁻¹ region of the IR spectrum of X shows a broad peak centered at 3250 cm⁻¹; the 680–840-cm⁻¹ region shows a strong peak at 830-cm⁻¹. The ¹H NMR spectrum of X gives the following: singlet at δ 1.3 (9H), singlet at δ 4.9 (1H), and multiplet at δ 7.0 (4H). What is the structure of X?