ERIC Number: EJ1073068
Record Type: Journal
Publication Date: 2015-Aug
Abstractor: As Provided
Reference Count: 14
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.
Descriptors: Organic Chemistry, Science Instruction, Laboratory Experiments, Science Experiments, Science Laboratories, Scientific Concepts, Spectroscopy, College Science, Undergraduate Study, Inquiry
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: firstname.lastname@example.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive; Guides - Classroom - Teacher
Education Level: Higher Education; Postsecondary Education
Authoring Institution: N/A