Resumen de An Introductory Organic Chemistry Review Homework Exercise: Deriving Potential Mechanisms for Glucose Ring Opening in Mutarotation
Margaret Murdock, R. W. Holman, Tyler Slade, Shelley L. D. Clark, Kenneth J. Rodnick
A unique homework assignment has been designed as a review exercise to be implemented near the end of the one-year undergraduate organic chemistry sequence. Within the framework of the exercise, students derive potential mechanisms for glucose ring opening in the aqueous mutarotation process. In this endeavor, 21 general review principles are addressed. The pedagogical approach employed is referred to as the question-guided, data-driven exercise. Students derive principles from answering questions posed and from the interpretation of provided structural (NMR spectroscopy) and kinetic data (generated in a 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 on one another and thus emphasize a student�s knowledge of each preceding concept. The concepts reviewed are as folllows: resonance structures, isomers, conformations, electrophiles, nucleophiles, thermodynamics versus kinetics, enthalpic and entropic considerations regarding intramolecular cyclization, hybridization, geometry, chirality, Brønsted-Lowry acid-base theory, pH, pKa, hydrogen bonding, and NMR spectroscopy (chemical shift, inductive effects on shielding and deshielding, spin-spin splitting, and integration).
