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  Home > JCE Print > Journal of Chemical Education > Issues > 2002  > April  >
In the Laboratory
The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience
María I. Colombo, María L. Bohn, and Edmundo A. Rúveda
Facultad de Ciencias Bioquímicas y Farmacéuticas, Instituto de Química Orgánica de Síntesis (CONICET-UNR), 2000 Rosario, Argentina
Cover
April 2002
Vol. 79 No. 4
p. 484
Abstract
Based on previously described experiments on the Ritter reaction between tert-butyl alcohol and benzonitrile in the presence of concentrated sulfuric acid and on the analysis of three computed hypothetical pathways, also previously described, Ritter reactions using the remaining three isomeric butyl alcohols in which Wagner-Meerwein rearrangements can take place are performed. From this information students are able to propose a mechanism for the Ritter reaction compatible with the experimental evidence they themselves obtained. The reactions are run simultaneously by groups of students under very simple experimental conditions, the reference compounds are prepared and characterized using melting point determination and IR and 1H NMR spectroscopy, and the reaction products are identified by TLC. Since the students have to share samples and information, they have a fruitful, cooperative learning experience.
Supplement
Instructions for students and notes for the instructor are available.
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*  Citation
 Colombo, María I.; Bohn, María L.; Rúveda, Edmundo A. J. Chem. Educ. 2002 79 484.
*  Keywords
 Collaborative / Cooperative Learning; Laboratory Instruction; Mechanisms; Organic Chemistry; Reactive Intermediates
*  History
 Created:
Last Updated:		 March 1, 2002
March 16, 2005
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