The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience

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.