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ERIC Number: EJ1240815
Record Type: Journal
Publication Date: 2020-Jan
Pages: 5
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Carbohydrate Characterization through Multidimensional NMR: An Undergraduate Organic Laboratory Experiment
Kennedy, Jacob S.; Larson, Garrett E.; Blumenfeld, Alex; Waynant, Kristopher V.
Journal of Chemical Education, v97 n1 p195-199 Jan 2020
Carbohydrates are an essential group of molecules to the organic chemistry classroom providing molecular relevance to a common ingredient in chemical biology. While the meticulous elucidation of the carbohydrate structures by Fischer and others is an engaging topic in the lecture, there are few laboratory experiments that can emulate carbohydrate complexity. Advanced and multidimensional NMR (2D NMR) techniques such as correlation spectroscopies (COrrelation SpectroscopY (COSY), [superscript 13]C Distortionless Enhancement by Polarization Transfer (DEPT), and HETeronuclear CORrelation (HETCOR) or Heteronuclear Single Quantum Coherence (HSQC)) have become more routine as they require less time on today's instruments and are taught more often in lecture. A laboratory experiment is described for second-year introductory undergraduate organic chemistry students that involves the transformation of nutraceutical N-acetyl-d-glucosamine to a-chloroglucosamine tetraacetate. After synthesis and simple workup, students collect four different NMR spectra from which they identify each [superscript 1]H signal in the product. Students learn to identify each signal's multiplicity and how multiple NMR experiments are used to characterize a product. Student confidence in NMR characterization was assessed on a small subset through postlab questions and pre- and postsurvey data.
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: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Evaluative
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A