Explain dimethylsulfide and water produced a single compound

Reference no: EM13335705

Thomas Jefferson Snodgrass (Jeff1 found an unlabelled reagent bottle in his -80 oC freezer. The bottle contained a liquid. He found that the compound (compound I) quickiy evaporated when warmed to room temperature. 'H-NMR of the compound showed. only two peaks, one, a triplet, was at 0.92 ppm and integrated to 6 protons and a second at 1.08 ppm that *u, u"., [(. [' quintet and integrated to 4 protons. Jeff treated the sample with Brz and light followed by sodium t-butoxide and isolated a new compound (Compound II which was also a gas at room temperature). NMR of compound II showed a doublet at 1.53 ppm that integrated to 6 protons and a quartet at 5.01 ppm that integrated to 2 protons. Treatment of compound 2 with Or followed by dimethylsulfide and water produced a single compound (compound IID. An IR spectrum of compound III had moderate peaks at2996,2836,2736, and 11 14 cm'l and a strong peak at l727cm'r. Use the clues in the story to identiff and draw the structures of compounds I, II, and III. You can figure out the chemistry without the spectroscopy.

Reference no: EM13335705

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