The terpene a-terpineol has the molecular formula C10H18O and is a constituent ofpine

Chapter 10, Problem 60

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The terpene a-terpineol has the molecular formula C10H18O and is a constituent ofpine oil. As the -ol ending in the name suggests, it is an alcohol. Use its 1H NMR spectrum(spectrum O, p. 443) to deduce as much as you can about the structure of a-terpineol. [Hints:(1) a-Terpineol has the same 1-methyl-4-(1-methylethyl)cyclohexane framework found in a numberof other terpenes (e.g., carvone, of Chapter 5). (2) In your analysis of spectrumO, concentrate on the most obvious features (peaks at d 5 1.1, 1.6, and 5.4) and use chemicalshifts, integrations, and the splitting of the d 5.4 signal (inset) to help you.]1H NMR6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.05.4

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