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ERIC Number: EJ1001197
Record Type: Journal
Publication Date: 2012-Jul
Pages: 3
Abstractor: As Provided
Reference Count: 8
ISSN: ISSN-0021-9584
Synthesis of a D-Glucopyranosyl Azide: Spectroscopic Evidence for Stereochemical Inversion in the S[subscript N]2 Reaction
Adesoye, Olumuyiwa G.; Mills, Isaac N.; Temelkoff, David P.; Jackson, John A.; Norris, Peter
Journal of Chemical Education, v89 n7 p943-945 Jul 2012
Stereospecific S[subscript N]2 conversion of configurationally pure acetobromoglucose (2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide) to the corresponding beta-D-glucopyranosyl azide is a useful exercise in the advanced organic undergraduate teaching laboratory. The procedure is safe and suitable for small-scale implementation, and firm proof of the stereochemical change is obtained from [superscript 1]H NMR coupling constants. The exercise provides students with experience in using important chiral pool natural product derivatives, reaction analysis by TLC, as well as careful product isolation, purification, and spectroscopic identification. (Contains 3 figures.)
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