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ERIC Number: EJ1048337
Record Type: Journal
Publication Date: 2014-Dec
Pages: 2
Abstractor: As Provided
Reference Count: 18
ISSN: ISSN-0021-9584
An Introductory Organic Chemistry Review Homework Exercise: Deriving Potential Mechanisms for Glucose Ring Opening in Mutarotation
Murdock, Margaret; Holman, R. W.; Slade, Tyler; Clark, Shelley L. D.; Rodnick, Kenneth J.
Journal of Chemical Education, v91 n12 p2146-2147 Dec 2014
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, pK[subscript a], hydrogen bonding, and NMR spectroscopy (chemical shift, inductive effects on shielding and deshielding, spin-spin splitting, and integration).
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A