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Organizing Organic Reactions: The Importance of Antibonding Orbitals

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David E. Lewis

Department of Chemistry, University of Wisconsin - Eau Claire, Eau Claire, WI 54702-4004

J. Chem. Educ., 1999, 76 (12), p 1718

DOI: 10.1021/ed076p1718

Publication Date (Web): December 1, 1999

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Subject):

Covalent Bonding

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

A Collaborative, Wiki-Based Organic Chemistry Project Incorporating Free Chemistry Software on the Web
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- A Collaborative, Wiki-Based Organic Chemistry Project Incorporating Free Chemistry Software on the Web
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  Journal of Chemical Education2011 88 (6), 764-768
  In recent years, postsecondary instructors have recognized the potential of wikis to transform the way students learn in a collaborative environment. However, few instructors have embraced in-depth student use of chemistry software for the creation of ...
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An Idea Whose Time Has Come? (the author replies)
David E. Lewis
Journal of Chemical Education2001 78 (6), 727
- An Idea Whose Time Has Come? (the author replies)
  David E. Lewis
  Journal of Chemical Education2001 78 (6), 727
  Unoccupied orbitals as the major arbiters of reactivity have been long ignored in teaching introductory organic chemistry courses.
  Abstract | Hi-Res PDF | PDF w/ Links
An Idea Whose Time Has Come?
William B. Jensen
Journal of Chemical Education2001 78 (6), 727
- An Idea Whose Time Has Come?
  William B. Jensen
  Journal of Chemical Education2001 78 (6), 727
  Past classifications related to the nine-category classification of organic electrophilic-nucleophilic reactions based on the bonding and symmetry characteristics of the reactants' frontier orbitals of the author.
  Abstract | Hi-Res PDF | PDF w/ Links