Research Experience for the Organic Chemistry Laboratory: A Student-Centered Optimization of a Microwave-Enhanced Williamson Ether Synthesis and GC Analysis

An inquiry-based experiment for the organic chemistry laboratory was developed to provide students with a cognitively rich research experience. Student teams were charged with optimizing the reaction conditions for the Williamson ether synthesis of 2-fluorophenetole from 2-fluorophenol, ethyl bromide, and potassium carbonate in either absolute ethanol or acetonitrile. Microwave acceleration of this SN2 reaction followed by rapid GC–MS analysis allowed students to review results, revise experimental conditions, and repeat the modified reaction and its analysis within a 3 h laboratory period. Variables that could be manipulated were reagent equivalencies, solvents and their volume, microwave reaction time, temperature, and wattage. Post-laboratory, all team data were available to the entire class for additional evaluation and each student was required to suggest new conditions for improvement in his/her laboratory report.