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ERIC Number: EJ820287
Record Type: Journal
Publication Date: 2006-Jul
Pages: 3
Abstractor: As Provided
Reference Count: 14
ISSN: ISSN-0021-9584
Stereospecific Synthesis of the Geometrical Isomers of a Natural Product
Grove, T.; DiLella, D.; Volker, E.
Journal of Chemical Education, v83 n7 p1055-1057 Jul 2006
Stereospecific synthesis of a geometrical isomer is not a common topic for the introductory organic chemistry laboratory. We have developed and tested an experiment for the synthesis of (Z) and (E) isomers that has been performed successfully by undergraduate students. The experiment is presented to the students as a puzzle in which they must determine the identity of the major component in anise oil. A necessary part of the analysis is the preparation the (E) and (Z) isomers of anethole. The Suzuki reaction of Pd(0)-catalyzed coupling between an aryl boronic acid and a vinyl halide is selected for these syntheses. Students typically synthesize the desired product with 95% selectivity. No special equipment is required and the products can be readily analyzed with GC-MS, NMR, and IR. Molecular modeling is used to explore the conformation of and the energy difference between the isomers. Several variations and extensions to the basic experiment are also described. (Contains 1 figure and 2 schemes.)
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A