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Integration of Computational and Preparative Techniques To Demonstrate Physical Organic Concepts in Synthetic Organic Chemistry: An Example Using Diels-Alder Reactions

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David R. J. Palmer

Department of Chemistry, University of Saskatchewan, Saskatoon, SK S7N 5C9, Canada

J. Chem. Educ., 2004, 81 (11), p 1633

DOI: 10.1021/ed081p1633

Publication Date (Web): November 1, 2004

Abstract

Preparative experiments in organic chemistry rarely invoke physical organic principles explicitly, even at the intermediate level where these principles are taught. Computational exercises often address such topics as molecular orbital theory and reaction energetics, but may not allow students to make the conceptual leap from computer to flask. The experiment described, based on endo–exo selectivity of Diels–Alder reactions, bridges this gap by integrating computational and preparative experiments.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Physical Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Computational Chemistry

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

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  We have developed and tested a computational laboratory that investigates an endo versus exo Diels–Alder cycloaddition. This laboratory employed density functional theory (DFT) calculations to study the cycloaddition of N-phenylmaleimide to furan. The ...
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Journal of Chemical Education2007 84 (2), 346
- The State of Organic Teaching Laboratories
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