Treatment of a-terpineol (Chapter 10, Problem 60) with aqueous mercuric acetate followed by sodium borohydride reduction leads predominantly to an isomer of the starting compound (C₁₀H₁₈O) instead of a hydration product. This isomer is the chief component in oil of eucalyptus and, appropriately enough, is called eucalyptol. It is popularly used as a flavoring for otherwise foul-tasting medicines because of its pleasant spicy taste and aroma. Deduce a structure for eucalyptol on the basis of sensible mechanistic chemistry and the following proton-decoupled ¹³C NMR data.

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CH3 1. Hg(OCCH,), H,O 2. NaBH,, H,O eucalyptol, 13C NMR: 8 = 22.8, 27.5, 28.8, 31.5, 32.9, 69.6, and 73.5 ppm (C10H180) (CH3)2COH a - Terpineol