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  Home > JCE Print > Journal of Chemical Education > Issues > 2009  > December  >
survey
In the Classroom
New Bouncing Curved Arrow Technique for the Depiction of Organic Mechanisms
Andrei R. Straumanis
Department of Chemistry and Biochemistry, College of Charleston, Charleston, SC 29424

Suzanne M. Ruder
Department of Chemistry, Virginia Commonwealth University, Richmond, VA 23284

Cover
December 2009
Vol. 86 No. 12
p. 1389
Abstract
Many students fail to develop a conceptual understanding of organic chemistry. Evidence suggests this failure goes hand-in-hand with a failure to grasp the techniques, meaning, and usefulness of curved arrow notation. Use of curved arrow notation to illustrate electrophilic addition appears to be a critical juncture in student understanding. Misconceptions arise because electrophilic addition is the first reaction where the curved arrow shows electrons from a pi bond forming a new bond that does not originate from a specific atom. This article describes a new technique (bouncing curved arrows) that addresses this stumbling block by designating which alkene carbon makes a bond to the electrophile. By removing this stumbling block and replacing it with a clear demonstration of the utility of curved arrows to describe regiochemistry of organic reactions, we encourage students to use curved arrows rather than rote memorization to deal with subsequent mechanisms. Student and faculty survey data are provided as evidence that both groups find bouncing curved arrows useful for describing electrophilic addition reactions, as well as electrophilic aromatic substitution reactions and carbocation rearrangements.
More Information
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Citation
Straumanis, Andrei R.; Ruder, Suzanne M. J. Chem. Educ. 2009, 86, 1389.
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Keywords
Collaborative / Cooperative Learning; Mechanisms of Reactions; Organic Chemistry; Problem Solving / Decision Making; Reactions; Second-Year Undergraduate; Student-Centered Learning; Synthesis; Upper-Division Undergraduate
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History
Created:
Last Updated:
10/22/2009
10/23/2009
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  Home > JCE Print > Journal of Chemical Education > Issues > 2009  > December  > Page 1389


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