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  Home > JCE Print > Journal of Chemical Education > Issues > 1999  > April  >
In the Classroom
The Discovery-Oriented Approach to Organic Chemistry. 1. Nitration of Unknown Organic Compounds. An Exercise in 1H NMR and 13C NMR Spectrosopy for Sophomore Organic Laboratories
Sonia R. McElveen, Kostas Gavardinas, Jean A. Stamberger, and Ram S. Mohan
Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61702
Cover
April 1999
Vol. 76 No. 4
p. 535
Abstract
Nitration is one of the most fundamental reactions in organic chemistry. However, the majority of the nitration experiments found in the standard lab textbooks are of the "cookbook" variety and convey none of the excitement associated with discovery in experimental chemistry. We have developed two simple nitration experiments that present the student with a puzzle and are a good exercise in 1H NMR and 13C NMR spectroscopy. 13 C NMR spectroscopy is a powerful structure elucidation tool and yet not many examples of the use of 13C NMR spectroscopy in organic lab experiments can be found. The experiment involves nitration of unknown organic compounds and product analysis by 1H NMR and 13C NMR spectroscopy, which enables the student to determine the identity of the unknown. In spite of the simplicity of the experiment, the element of discovery ensures that student interest and enthusiasm are retained.
Supplement
The student handout for this experiment is a Microsoft Word document and the eight NMR Spectra are Photoshop JPEG files. The Word and JPEG files have been compressed into both zip (for Windows) and sit (for Macintosh) files. The material can also be accessed as a pdf file using Acrobat Reader.
*  Contents
*  Download
supp535.pdf

supp535.zip

supp535.sit
More Information
*  Citation
 McElveen, Sonia R.; Gavardinas, Kostas; Stamberger, Jean A.; Mohan, Ram S. J. Chem. Educ. 1999 76 535.
*  Keywords
 Inquiry-Based / Discovery Method; NMR Spectrometry; Organic Chemistry; Nitration
*  History
 Created:
Last Updated:		 June 14, 1999
November 22, 2005
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