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A one-day laboratory epoxidation experiment, requiring no purification, is described, wherein the students are given an “unknown” stereoisomer of 3-hexen-1-ol, and use 1H NMR coupling constants to determine the stereochemistry of their product. From this they work backward to determine the stereochemistry of their starting alkene.
Treadwell et al. (Fri,) studied this question.
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