Abstract
A guided inquiry-based experiment exploring the regioselectivity of the hydration of phenylacetylene is described. The experiment uses an acidic gold(III) catalyst in a benign methanol/water solvent system to introduce students to alkyne chemistry and key principles of green chemistry. The experiment can be easily completed in approximately 2 h, and is suitable for use in introductory organic chemistry laboratories. The experiment is versatile and amenable to many lab settings, as it requires no specialized glassware, and the crude product can be analyzed via gas chromatography, infrared spectroscopy, or nuclear magnetic resonance spectroscopy.
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