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  Home > JCE Print > Journal of Chemical Education > Issues > 1999  > December  >
Research: Science and Education
Organizing Organic Reactions: The Importance of Antibonding Orbitals
David E. Lewis
Department of Chemistry, University of Wisconsin - Eau Claire, Eau Claire, WI 54702-4004
Cover
December 1999
Vol. 76 No. 12
p. 1718
Abstract
The process of making and breaking covalent bonds in intermolecular reactions always involves the movement of electrons from one reacting species to the other. It is accepted that the LUMO is intimately involved in organic reactions requiring transfer of a pair of electrons from one reactant to the other. However, unoccupied orbitals and their involvement in organic reactions are seldom discussed at length in undergraduate courses in organic chemistry, with the possible exception of the empty 2p orbital in boranes and carbocations. It is proposed that unoccupied molecular orbitals arbitrate much organic reactivity, and that they provide the basis for a reactivity-based system for organizing organic reactions. Such a system is proposed for organizing organic reactions according to principles of reactivity, and the system is discussed with examples of the frontier orbitals involved.

See Letter re: this article.
More Information
*  Citation
 Lewis, David E. J. Chem. Educ. 1999 76 1718.
*  Keywords
 Organic Chemistry; Teaching / Learning Aids; Bonding Theory; Mechanisms; MO Theory
*  History
 Created:
Last Updated:		 November 10, 1999
June 23, 2005
Link to Letter added (April 2004).
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