Treatment of the following ketone with LAH affords two products, A and B. Compound B has
Chapter 20, Problem 20.95(choose chapter or problem)
Treatment of the following ketone with LAH affords two products, A and B. Compound B has a molecular formula of C8H14O and exhibits strong signals at 3305 cm-1 (broad) and 2117 cm-1 in its IR spectrum (J. Am. Chem. Soc. 2006, 128, 64996507): OTf O OTf OH A + 1) LAH B (C8H14O) 2) H2O ? (a) Using the following 1 H NMR data, deduce the structure of compound B: 0.89 d (6H, singlet), 1.49 d (1H, broad singlet), 1.56 d (2H, triplet), 1.95 d (1H, singlet), 2.19 d (2H, triplet), 3.35 d (2H, singlet). (b) Provide a plausible mechanism to account for the formation of compound B. (Hint: Tf = triflate, Section 7.8.)
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