A compound X with the molecular formula C₅H₁₀O₂ has an IR spectrum with strong absorption in the 1000–1100 cm^–1 region; very strong, broad absorption in the 3000–3600 cm^–1 region; and no absorption in the 1600–1700 cm^–1 region. The proton NMR spectrum of X is given in Fig. P13.59. When the sample is shaken with D₂O, the triplet at δ 3.5 disappears and the doublet at δ 3.7 becomes a singlet. Propose a structure for this compound, and explain your reasoning carefully.

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2400 absorption 2100 7 1800 5.9 Hz 6 1500 5.9 Hz 5 chemical shift, Hz 1200 900 2H 2H 5.1 Hz 2H 1H 5.1 Hz 4 3 chemical shift, ppm (8) 600 2 3H 300 0 Figure P13.59 The proton NMR spectrum for Problem 13.59. The integrals (red) are the actual numbers of hydrogens, and the violet numbers are coupling constants.