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Teaching Reaction Mechanisms Using the Curved Arrow Neglect (CAN) Method

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John H. Penn and Abdulrahman G. Al-Shammari

Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045

J. Chem. Educ., 2008, 85 (9), p 1291

DOI: 10.1021/ed085p1291

Publication Date (Web): September 1, 2008

Section:

History, Education, and Documentation

Abstract

A new method for teaching organic reaction mechanisms that can be used in a computer-assisted Instruction (CAI) environment is proposed and tested. The method concentrates on the intermediate structures that are assumed to be on the reaction coordinate and that can be evaluated and graded by currently available computer techniques. The "curved arrows" that show the electron flow in a reaction mechanism are neglected since they cannot be evaluated and graded with currently available computer techniques. We have termed this strategy the "curved arrow neglect" method for teaching organic reaction mechanisms (i.e., the CAN method). By allowing students to practice organic reaction mechanisms using the CAN method, student performance in drawing traditional reaction mechanisms, in which students had to include the "curved arrows" on their written classroom exams, was significantly enhanced. This CAN method for describing reaction mechanisms can be used in any CAI package currently available or to be developed. It requires only proper incorporation of the individual chemical structures of the CAN mechanism into an appropriate learning format (e.g., flash cards, CAI technique).