Does the Solvent Affect the Relative Nucleophilic Strength of Halide Ions in an SN2 Type Reaction?
Terrence P. Sherlock, Ralph Fleming, Ryan Oesterle, and Jared Styer. Burlington County College, Mount Laurel, NJ As part of our first semester organic chemistry laboratory course, our students have traditionally run a version of a classic textbook experiment that complements their study of mechanisms in nucleophilic substitution reactions. In the experiment, bromide and chloride ions are competing nucleophiles in an SN2 type reaction with 1-butanol in aqueous solution. Typical results indicate the ratio of brominated product to chlorinated product to be on the order of 10:1. Students have been curious whether, as their textbook predicts, this ratio could be affected by proper selection of solvents. Experiments were designed and conducted to test this theory, and the results will be presented.
