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ERIC Number: EJ925961
Record Type: Journal
Publication Date: 2011-Mar
Pages: 3
Abstractor: As Provided
Reference Count: 27
ISBN: N/A
ISSN: ISSN-0021-9584
Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate [superscript 1]H NMR Experiment to Introduce Chiral Chemistry
Faraldos, Juan A.; Giner, Jos-Luis; Smith, David H.; Wilson, Mark; Ronhovde, Kyla; Wilson, Erin; Clevette, David; Holmes, Andrea E.; Rouhier, Kerry
Journal of Chemical Education, v88 n3 p334-336 Mar 2011
This organic laboratory experiment introduces students to stereoselective enzyme reactions, resolution of enantiomers, and NMR analysis of diastereomers. The reaction between racemic 1-phenylethanol and vinyl acetate in hexane to form an ester is catalyzed by acylase I. The unreacted alcohol is then treated with a chiral acid and the resulting ester diastereomer is analyzed by NMR. This experiment is suitable for group work in the laboratory as several diastereomers are synthesized and compared to determine which enantiomer of 1-phenylethanol reacts with the enzyme. (Contains 2 schemes and 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: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A