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New Bouncing Curved Arrow Technique for the Depiction of Organic Mechanisms

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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

J. Chem. Educ., 2009, 86 (12), p 1389

DOI: 10.1021/ed086p1389

Publication Date (Web): December 1, 2009

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Collaborative / Cooperative Learning

Keywords (Subject):

Mechanisms of Reactions

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

A Method for Writing Open-Ended Curved Arrow Notation Questions for Multiple-Choice Exams and Electronic-Response Systems
Andrei R. Straumanis , Suzanne M. Ruder
Journal of Chemical Education2009 86 (12), 1392
- A Method for Writing Open-Ended Curved Arrow Notation Questions for Multiple-Choice Exams and Electronic-Response Systems
  Andrei R. Straumanis , Suzanne M. Ruder
  Journal of Chemical Education2009 86 (12), 1392
  A critical stage in the process of developing a conceptual understanding of organic chemistry is learning to use curved arrow notation. From this stems the ability to predict reaction products and mechanisms beyond the realm of memorization. Since ...
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