Discovering Electronic Effects of Substituents in Nitrations of Benzene Derivatives Using GC–MS Analysis

Malgorzata M. Clennan and Edward L. Clennan
Department of Chemistry, University of Wyoming, Laramie, WY 82071
J. Chem. Educ., 2007, 84 (10), p 1679
DOI: 10.1021/ed084p1679
Publication Date (Web): October 1, 2007

Abstract

The nitration of six benzene derivatives having a range of substituents that differ in electronic effects were followed by GC–MS analyses of the crude reaction mixtures and adapted for the second-year organic laboratory. Students pool their results and identify the products by analyzing the mass spectral data of the isomers and by comparing them to the GC–MS analysis of authentic samples. Students determine which substituents predominantly direct nitration to the ortho- or para- and to the meta positions. This simple discovery-oriented experiment illustrates and reinforces the lecture material and provides students with first-hand knowledge of how textbook conclusions are determined in a laboratory situation.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Aromatic Compounds
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  • Received: August 03, 2009

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