A compound X with the molecular formula C5H10O2 has an IR spectrum with strong
Chapter 13, Problem 13.59(choose chapter or problem)
A compound X with the molecular formula C5H10O2 has an IR spectrum with strong absorption in the 10001100 cm1 region; very strong, broad absorption in the 30003600 cm1 region; and no absorption in the 16001700 cm1 region. The proton NMR spectrum of X is given in Fig. P13.59. When the sample is shaken with D2O, the triplet at d 3.5 disappears and the doublet at d 3.7 becomes a singlet. Propose a structure for this compound, and explain your reasoning carefully.
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