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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > October  >
In the Laboratory
Green Chemistry
A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory
Eric Eby and S. Todd Deal
Department of Chemistry, Georgia Southern University, Statesboro, GA 30460
Cover
October 2008
Vol. 85 No. 10
p. 1426

Abstract
We developed an alternative electrophilic aromatic substitution reaction for the organic chemistry teaching laboratory. The experiment is an electrophilic iodination reaction of salicylamide, a popular analgesic, using environmentally friendly reagents—sodium iodide and household bleach. Further, we designed the lab as a guided-inquiry experiment, asking the students first to predict the orientation of the substitution reaction. After synthesizing the product, the students are asked to determine its structure using FT-IR spectroscopy. The choice of this method of characterization was intentional because of the utility of infrared spectroscopy in determining substitution patterns on aromatic rings and also because it requires students to analyze the fingerprint region of the spectrum. Given that most classroom instruction on IR focuses on functional group determination, we believe this is an added benefit to this experiment.
Supplement
Student handouts; Instructor notes
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Contents
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Citation
Eby, Eric; Deal, S. Todd. J. Chem. Educ. 2008, 85, 1426.
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Keywords
Aromatic Compounds; Constitutional Isomers; Electrophilic Substitution; Green Chemistry; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; IR Spectroscopy; Laboratory Instruction; Organic Chemistry; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
8/27/2008
9/5/2008
 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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