Raman Spectroscopy in the Organic Chemistry Laboratory: The Formation of N-Carboxy-2-imidazolidone

Abstract

The use of Raman spectroscopy in industry and academia has expanded aided by the rapid development of computer technology and instrument availability. Nonetheless, Raman spectroscopy is still underutilized in the undergraduate chemistry curriculum. Herein, a laboratory exercise is described in which students in the organic chemistry course are introduced to the concepts of Raman spectroscopy at the same time that they study melting point and recrystallization techniques. In this laboratory, students determine the melting point of 2-imidazolidone and N-methoxycarbonyl-2-imidazolidone and use Raman spectroscopy to study vibrational signatures of their functional groups. Additionally, Raman is used to examine the production of N-carboxy-2-imidazolidone from N-methoxycarbonyl-2-imidazolidone and the subsequent spontaneous decarboxylation to 2-imidazolidone. This laboratory experiment permits students to learn about physical properties of organic molecules, functional groups, and spectroscopy early in the introductory organic chemistry course. As a result, students add to the number of learned laboratory techniques they can use in future experiments in the organic chemistry laboratory and other chemistry courses.