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  Home > JCE Print > Journal of Chemical Education > Issues > 2007  > December  >
In the Laboratory
Computational Analysis of Stereospecificity in the Cope Rearrangement
Laura Glish and Timothy W. Hanks
Department of Chemistry, Furman University, Greenville, SC 29613
Cover
December 2007
Vol. 84 No. 12
p. 2001

Abstract
The Cope rearrangement is a highly stereospecific, concerted reaction of considerable synthetic utility. Experimental product distributions from the reaction of disubstituted 1,5-hexadienes can be readily understood by computer modeling of the various possible transitions states. Semi-empirical methods give relative energies of transition states that parallel those of more sophisticated methods at a fraction of the computational time. Visual analysis of computed transition-state geometries allow students to interpret the computational results by analogy to the familiar chair and boat conformations of substituted cyclohexanes.
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Detailed instructions for students, a suggested format for the laboratory report, and instructor notes are available.
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Citation
Glish, Laura; Hanks, Timothy W. J. Chem. Educ. 2007, 84, 2001.
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Keywords
Alkenes; Computational Chemistry; Computer-Based Learning; Conformational Analysis; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; Mechanisms of Reactions; MO Theory; Molecular Modeling; Organic Chemistry; Second-Year Undergraduate; Upper-Division Undergraduate
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History
Created:
Last Updated:
10/25/2007
10/31/2007
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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