This work explored using the hydration of alkenes via hydroboration-oxidation as a means of fostering transformative learning and development of critical thinking skills in the undergraduate chemistry laboratory. Second-year undergraduate chemistry students were introduced to the hydroboration-oxidation of simple alkenes in a lecture setting and then given the task of developing a laboratory procedure. Conditions were explored and optimized by students with minimal instructor intervention. After developing a set of conditions that reliably converted 1-octene to 1-octanol, students were tasked with hydrating incrementally more complex alkene substrates. Along the way students were introduced to common analytical tools used by research chemists. At the end of the semester students successfully demonstrated conversion of (3β)-cholest-5-en-3-ol to (3β,5α,6α)-cholestane-3,6-diol using infrared spectroscopy, 1D and 2D proton, carbon, and variable temperature nuclear magnetic resonance spectroscopy, and mass spectrometry.

Hydroboration-oxidation reactions as a pathway for transformative learning and development of critical thinking skills in the undergraduate chemistry laboratory

2019 Fall National Meeting

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