You Have Just Been Named President Of The Famous Perfume

You have just been named president of the famous perfume company. Scents “R” Us Searching for a hot new item to market, you run across a bottle labeled only C10lH26O, which contains a liquid with a wonderfully sweet rose aroma. You want more, so you set out to elucidate its structure. Do so from the following data, (i) 1H NMR: clear signals at δ = 0.94 (d, J = 7 Hz. 3 H), 1.63 (s, 3 H). 1.71 (s, 3 H), 3.68 (t, J = 7 Hz. 2 H). 5.10 (t. J = 6 Hz, 1 H) ppm: the other 8 H have overlapping absorptions in the range δ = 1.3-2.2 ppm. (ii) l3C NMR (1H decoupled): δ = 60.7. 125.0. 130.9 ppm: seven other signals are upheld of δ = 40 ppm. (iii) IR: v = 1640 and 3350 cm-1, (iv) Oxidation with buffered PCC (Section 8-6) gives a compound with the molecular formula C10H18O. Its spectra show the following changes compared with the starting material: 1H NMR: signal at δ = 3.68 ppm is gone, but a new signal is seen at δ = 9.64 ppm: 13C NMR: signal at δ = 60.7 ppm is gone, replaced by one at δ = 202.1 ppm; IR: loss of signal at v = 3350 cm-1; new peak at v = 1728 cm” (v) Hydrogenation gives C10H22O, identical with that formed on hydrogenation of the natural product geraniol (see margin).

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