Part I: Synthesis of functionalized bile acids towards the construction of steroidal macrocycles. Part II: Evaluation and expansion of a modular card game for teaching organic chemistry
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In Part I, the synthesis of chenodeoxychoic acid (CDCA) derivatives towards the construction of unique chemical architectures are reported. Building on previously described methods, CDCA based macrocycles with inner cavities have been synthesized and characterized. Attempts toward oxa-Michael coupling of CDCA monomers to form sulfonate ester linked dimmers is described. CDCA was also functionalized with terminal alkynes (pentynyl, hexynyl, and heptynyl) and aryl iodide and cyclized to from the respective macrocycles. These have been coupled together via oxygen-free Sonogashira reaction conditions to form large barrel-like steroidal architectures. These structures were investigated by 1H NMR, 13C NMR spectroscopy, and HR-MS, and MALDI-TOF spectroscopy. In part II a game to teach organic chemistry, ChemKarta was evaluated as a teaching tool. Analysis of an undergraduate class’s impressions of the game showed that Chemkarta was an easy to learn and enjoyable game, but the amount of information in the game could be overwhelming for some students. Furthermore, the modular nature of the game was demonstrated by developing new cards to fit into the examined card set, as well as additional card sets to teach different subjects using the same game rules.
Table of Contents
Introduction -- Literature review -- Oxa-Michael strategies toward CDCA dimers -- Synthesis of bile acids derivatives towards macrocycle construction via Sonogashara coupling -- Evaluation and expansion of Chemkarta -- Conclusion -- Appendix A. Functional groups -- Appendix B. Functional Groups Victory and Technique Cards --Appendix C. Structure and bonding -- Appendix D. Name reactions
Ph.D. (Doctor of Philosophy)