Modern methods in chemical synthesis are enabling the direct and selective manipulation of carbon-hydrogen bonds using transition metal catalysis. Still, the concept of carbon-hydrogen bond functionalization remains largely absent in the undergraduate curricula. This presentation will outline a laboratory project on carbon-hydrogen bond functionalization intended for advanced undergraduate students.  The lab has been designed to emphasize concepts in both inorganic and organic synthesis, product mixture analysis and separation, reaction kinetics, and spectroscopy.  Students are required to review recent chemical literature, develop a research proposal in concert with the lab instructor and teaching assistant, and execute the design plan.  Students performing this lab gain an appreciation for modern chemical catalysis, transition metal-mediated reaction mechanisms, and the power of C�H bond oxidation to transform ordinary starting materials into value-added materials. The Stanford Chemistry curriculum consists of three quarters of chemical synthesis lab with the first emphasizing basic laboratory technique, the second emphasizing spectroscopy, and the third emphasizing organic and inorganic synthesis. The first two courses are large enrollment courses open to all majors, and the last course is designed specifically for chemistry majors and is often deemed as a capstone course to prepare students for undergraduate research in organic chemistry. The course includes several extended projects with topics including multi-component assembly, asymmetric catalysis, and organometallics. The conclusion of the course is a student designed project that consists of a literature review, written proposal, and execution of a novel synthetic sequence. The most recent quarter emphasized a partnership with an organic research lab to incorporate cutting edge carbon-hydrogen functionalization research with the undergraduate curriculum.

Bridging the gap between research and teaching: A C-H insertion project

246th National Meeting (2013)

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