A unique homework assignment has been designed as a review exercise to be implemented near the end of the one-year organic chemistry sequence. Within the framework of the exercise, the student will derive potential mechanisms for glucose ring opening in the mutarotation process. In this endeavor, twenty-one general review principles are addressed. The pedagogical approach employed is referred to as the question-guided data-driven exercise (QGDDE). Students derive principles from answering questions posed and from the interpretation of provided structural (nuclear magnetic resonance spectroscopy) and kinetic data (generated in our research laboratory). An emphasis on designing experiments to address specific questions is incorporated throughout. The questions posited, and the data provided, are formulated to build upon one another and thus emphasize a student's knowledge of each preceding concept. The QGDDE is designed to ensure that students leave organic chemistry with a firm grasp of the skills that enable them to design experiments so as to test a hypothesis, organize and interpret data and, in this case, forward a defensible mechanism for glucose ring opening in the mutarotation process. The goal is to better enable students to succeed when challenged with the task of interpreting data in an open-ended research setting within the framework of reviewing many organic chemistry fundamentals while deriving a mechanism from provided data. The concepts reviewed are: resonance structures, isomers, conformations, electrophiles, nucleophiles, thermodynamics vs. kinetics, enthalpic and entropic considerations regarding intramolecular cyclization, hybridization, geometry, chirality, Bronstead-Lowry acid/base theory, pH, pKa, hydrogen bonding, and nuclear magnetic resonance spectroscopy (chemical shift, inductive effects on shielding and deshielding, spin-spin splitting and integration).

Organic chemistry review homework exercise: Deriving potential mechanisms for glucose ring opening in mutarotation

248th National Meeting (2014)

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