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ERIC Number: EJ918444
Record Type: Journal
Publication Date: 2010-Jul
Pages: 3
Abstractor: As Provided
Reference Count: 20
ISSN: ISSN-0021-9584
Glycosidation of Methanol with Ribose: An Interdisciplinary Undergraduate Laboratory Experiment
Simon, Erin; Cook, Katie; Pritchard, Meredith R.; Stripe, Wayne; Bruch, Martha; Bendinskas, Kestutis
Journal of Chemical Education, v87 n7 p739-741 Jul 2010
This exercise provides students hands-on experience with the topics of glycosidation, hemiacetal and acetal formation, proton nuclear magnetic resonance ([superscript 1]H NMR) spectroscopy, and kinetic and thermodynamic product formation. In this laboratory experiment, the methyl acetal of ribose is synthesized, and the kinetic and thermodynamic products of the reaction are identified using a 300 MHz NMR spectrometer with a variable temperature probe. The results of this reaction under two different sets of conditions reveal that alpha forms of ribosides are less stable than beta forms and that the kinetic products are furanosides, whereas the thermodynamic products are pyranosides. It can be performed as a single 3-h laboratory session or as a series of several sessions if students collect their own NMR spectra and use longer reaction times. (Contains 1 table, 4 figures and 2 notes.)
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
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A