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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > April  >
In the Laboratory
A Nitration Reaction Puzzle for the Organic Chemistry Laboratory
Milton J. Wieder and Russell Barrows
Department of Chemistry, Metropolitan State College of Denver, Denver, CO 80217-3362
Cover
April 2008
Vol. 85 No. 4
p. 549

Abstract
Treatment of phenylacetic acid with 90% HNO3 yields a product, I, whose observed melting point is 175–179 °C and whose equivalent weight is approximately 226 grams. Treatment of phenylacetic acid with 70% HNO3 yields a product, II, whose observed melting point is 106–111 °C and whose equivalent weight is approximately 181 grams. Based on these data and 1H NMR and infrared spectral data, students are asked to deduce the structures of nitration products I and II. The above nitration experiment illustrates fundamental electrophilic aromatic substitution concepts while posing an interesting structure elucidation puzzle for organic chemistry students. The nitration of phenylacetic acid requires students to ponder the directing ability of the carboxymethyl group. Given that nitric acid is a powerful oxidizing agent, students must also ponder whether the carboxymethyl group is subject to oxidation under the reaction conditions employed. Lastly, students must determine what impact, if any, the concentration of the nitric acid used will have on the structures of the nitration products obtained.
Supplement
Student handouts; Instructor notes; Spectra
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Citation
Wieder, Milton J.; Barrows, Russell. J. Chem. Educ. 2008, 85, 549.
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Keywords
Constitutional Isomers; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; Mass Spectrometry; NMR Spectroscopy; Organic Chemistry; Problem Solving / Decision Making; Second-Year Undergraduate; Synthesis; Titration / Volumetric Analysis
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History
Created:
Last Updated:
2/26/2008
3/5/2008
 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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