Explain h-nmr of the compound showed only two peaks

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Reference no: EM13334080

Thomas Jefferson Snodgrass found an unlabelled reagent bottle in his -80 C freezer. The Bottle contained a liquid. He found that the compound( compound 1) quickly evaporated when warmed to room temperature. H-NMR of the compound showed only two peaks, one, a triplet, was at .92 ppm and integrated to 6 protons and a second at 1.08 ppm that was a quintet and integrated to 4 protons. Jeff treated the sample with Br2 and light followed by sodium t-butoxide and isolated a new compound( compound 2 which was also a gas at room temperature). NMR of compound 2 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 O3 followed by dimethylsulfide and water produced a single compound ( compound 3). An IR spectrum of compound 3 had moderate peaks at 2996, 2836, 2736 and 1114 cm-1 and a strong peak at 1727 cm-1. Use the cluse in the story to identify and draw the structures of compounds 1, 2, and 3.

Reference no: EM13334080

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