Epoxidation with Possibilities: Discovering Stereochemistry in Organic Chemistry via Coupling Constants

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.