Novel applications of microwave chemistry and modern analytical methods toward the development of versatile unknowns-based experiments in the sophomore organic chemistry laboratory
Jackson, Douglas Michael
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Developing laboratory experiments that effectively engage, instruct, and assess student performance is a critical challenge for the undergraduate organic chemistry laboratory. The limitations of traditional “cookbook” reactions have been well discussed in the literature and include but are certainly not limited to: “foolproof recipes”, limited engagement, and lack of problem solving. Additionally, given the breadth of Internet resources and student access to old lab reports, novel experiments are needed that are versatile enough to remain pedagogically relevant. Major approaches to combat this nontrivial issue include integration of elements of “discovery” or problem solving, student driven inquiry methods, and experimental unknowns. Modern analytical techniques notably lacking in traditional educational experiments including IR spectroscopy, GC, and NMR spectroscopy are employed in order to directly assess student performance and comprehension. A strict commitment to increased experimental variability and unknown elements has been employed in the development of each experiment. Increased individual assessment and the possibility of multiple experimental outcomes require students to more carefully plan and conduct experiments and analyze their own data rather than copy from an old report. Careful experimental design is required in order to adhere to the 3-hour lab period employed by most universities. Addressing this issue, the present work makes use of time saving microwave chemistry and PicoSpin™ bench-top NMRs. Several educational experiments will be highlighted that have been researched, developed, and implemented in the University of Georgia sophomore organic chemistry laboratory program. A newly developed synthetic method for the decarboxylation of amino acids has been integrated into an educational experiment featuring use of both microwave chemistry and the PicoSpin™ NMRs. A novel method for stereoselective “tuning” allows instructors to vary student outcomes of a stereoselective Luche reduction. A new discovery experiment emphasizing critical thinking skills has been developed wherein students combine their experimental data to discover a trend in epoxide ring-opening reactions. Additionally, a microwave Fischer esterification protocol has also been outfitted for inclusion of PicoSpin™ NMR analysis. This work constitutes a significant contribution to the organic chemistry educational literature.