Article
A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory
J. Chem. Educ.
(2008)
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.
Keywords
- Aromatic Compounds,
- Hands-On Learning / Manipulatives,
- Green Chemistry,
- Organic Chemistry
Disciplines
Publication Date
October 1, 2008
DOI
10.1021/ed085p1426
Citation Information
Eric Eby and S. Todd Deal. "A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory" J. Chem. Educ. Vol. 85 Iss. 10 (2008) p. 1426 Available at: http://works.bepress.com/stodd-deal/2/