"Green" electrophilic aromatic substitution for the organic chemistry laboratory

CHED 227

Eric Eby, f4ll3n4ng3l@frontiernet.net and S. Todd Deal, stdeal@georgiasouthern.edu. Department of Chemistry, Georgia Southern University, PO Box 8064, Statesboro, GA 30460
We have developed an environmentally friendly electrophilic aromatic substitution reaction for the organic chemistry laboratory. The experiment utilizes sodium hypochlorite (bleach) and sodium iodide to generate the electrophilic iodine species, which is then reacted with salicylamide (an analgesic). Students are asked to predict the orientation of substitution from their understanding of directing effects. They use FT-IR spectroscopy to ascertain the structure of the product.