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ERIC Number: EJ1073068
Record Type: Journal
Publication Date: 2015-Aug
Pages: 4
Abstractor: As Provided
Reference Count: 14
ISBN: N/A
ISSN: ISSN-0021-9584
Illustrating the Utility of X-Ray Crystallography for Structure Elucidation through a Tandem Aldol Condensation/Diels-Alder Reaction Sequence
Hoang, Giang T.; Kubo, Tomohiro; Young, Victor G., Jr.; Kautzky, Jacob A.; Wissinger, Jane E.
Journal of Chemical Education, v92 n8 p1381-1384 Aug 2015
Two introductory organic chemistry laboratory experiments are described based on the Diels-Alder reaction of 2,3,4,5-tetraphenylcyclopentadienone, which is synthesized prior to or in a one-pot reaction, with styrene. Students are presented with three possible products, the "endo" and "exo" diastereomers and the decarbonylated product, for the beautiful crystalline compound isolated. Analysis by IR and [superscript 1]H NMR spectroscopy aid investigators in proposing an initial structure for the product, but the solved X-ray crystal structure provides unequivocal evidence of its stereochemistry. Both versions of the synthesis introduce two important and atom economical reactions, employ the Karplus relationship for [superscript 1]H NMR interpretation, and illustrate the power of X-ray crystallography for molecular structure determination.
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; Guides - Classroom - Teacher
Education Level: Higher Education; Postsecondary Education
Audience: Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A