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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > November  >
In the Laboratory
A More Challenging Interpretative Nitration Experiment Employing Substituted Benzoic Acids and Acetanilides
Edward M. Treadwell and Tung-Yin Lin
Department of Chemistry, Eastern Illinois University, Charleston, IL 61920
Cover
November 2008
Vol. 85 No. 11
p. 1541

Abstract
An experiment is described involving the nitration of ortho or meta monosubstituted benzoic acids (XC6H4CO2H, X = Halogen, Me, OH, or OMe) and monochlorinated acetanilides with nitric acid to determine the regioselectivity of addition by 1H NMR spectroscopy and molecular modeling. Students were able to interpret the 1H NMR spectra regardless of the formation of multiple products or contamination from the starting materials. With one exception, both the 1H NMR spectroscopy and computational methods agreed with the theoretical expectation and provided a nice demonstration of regioselectivity of nitration on substituted benzene.
Supplement
Student handouts; Instructor notes including 1H NMR spectral data
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Contents
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Citation
Treadwell, Edward M.; Lin, Tung-Yin. J. Chem. Educ. 2008, 85, 1541.
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Keywords
Aromatic Compounds; Computational Chemistry; Electrophilic Substitution; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; Molecular Modeling; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
9/19/2008
9/25/2008
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
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