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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > July  >
In the Laboratory
Stereospecific Synthesis of the Geometrical Isomers of a Natural Product
T. Grove, D. DiLella, and E. Volker
Department of Chemistry, Shepherd University, Shepherdstown, WV 25443
Cover
July 2006
Vol. 83 No. 7
p. 1055
Abstract
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.
Supplement
A student handout and much detailed information for the instructor so that the experiment can be modified to fit the instructor's needs are available. Complete details and sample data for the chromatography and spectroscopy are provided. Results for some modeling exercises are also provided. Procedures are included for a number of alternative synthetic routes to anethole including the dehydration of 1-(4-methoxyphenyl)-1-propanol.
*  Contents JCE2006p1055W.doc (Microsoft Word)
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*  Citation
 Grove, T.; DiLella, D.; Volker, E. J. Chem. Educ. 2006 83 1055.
*  Keywords
 Alkenes; Computational Chemistry; Gas Chromatography; Hands-On Learning / Manipulatives; IR Spectroscopy; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Stereochemistry; Synthesis; Upper-Division Undergraduate
*  History
 Created:
Last Updated:		 5/26/2006
5/31/2006
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