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Saying What You Mean: Teaching Mechanisms in Organic Chemistry

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J. Brent Friesen

Department of Natural Science, Rosary College of Arts and Sciences, Dominican University, River Forest, IL 60305

J. Chem. Educ., 2008, 85 (11), p 1515

DOI: 10.1021/ed085p1515

Publication Date (Web): November 1, 2008

Section:

History, Education, and Documentation

Abstract

Organic reactions in introductory organic chemistry courses are most commonly taught with a mechanism-based approach to the understanding of molecular reactivity. However, the effectiveness of the popular curved arrow representation to describe reaction mechanisms is often compromised by the overuse of shortcuts and obscure notation. The consistent use of balanced reaction equations, a concept that most students have learned and practiced in previous chemistry courses, is an effective technique in communicating reaction mechanisms. Other ways to introduce clarity and consistency to reaction mechanisms are: (i) avoiding the use of shortcut notations, (ii) including key electrons and bonds in structural representations, and (iii) distinguishing between covalent and ionic bonds.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Analogies / Transfer

Keywords (Subject):

Learning Theories

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

Telling It Like It Is: Teaching Mechanisms in Organic Chemistry
Addison Ault
Journal of Chemical Education2010 87 (9), 937-941
- Telling It Like It Is: Teaching Mechanisms in Organic Chemistry
  Addison Ault
  Journal of Chemical Education2010 87 (9), 937-941
  In this article I support and extend the ideas presented by J. Brent Friesen in his article Saying What You Mean; Teaching Mechanisms in Organic Chemistry (JCE November, 2008). I emphasize “telling the truth” about proton transfers. The truth is that in ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Rearrangements of Allylic Sulfinates to Sulfones: A Mechanistic Study
David B. Ball, Paul Mollard and Karl R. Voigtritter, Jenelle L. Ball
Journal of Chemical Education2010 87 (7), 717-720
- Rearrangements of Allylic Sulfinates to Sulfones: A Mechanistic Study
  David B. Ball, Paul Mollard and Karl R. Voigtritter, Jenelle L. Ball
  Journal of Chemical Education2010 87 (7), 717-720
  Most current organic chemistry textbooks are organized by functional groups and those of us who teach organic chemistry use functional-group organization in our courses but ask students to learn organic chemistry from a mechanistic approach. To enrich and ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links