Williamson ether synthesis is a reaction between an alkyl halide and a deprotonated alcohol, which can be used to demonstrate substitution to organic students. The reaction between (1-bromoethyl)benzene and ethanol deprotonated by NaOH was optimized for time, substrate concentration, and heating methods. Full conversion with moderate yields was achieved after a total of 30 minutes at 75 °C using pressure vial heating instead of traditional reflux. The ethanol substrate served as the reaction solvent and could easily be removed from the product after the reaction during aqueous work-up due to its miscibility with water. The ether product contains distinctive <sup>1</sup>H NMR signals located at unique locations relative to the (1-bromoethyl)benzene allowing for simple determination of percent conversion and purity by analyzing integrations. Additional analysis methods including TLC and GC, as well as alternative benzyl halide substrates, were also tested.

Development of an undergraduate pedagogical laboratory experiment for Williamson ether synthesis

ACS Fall 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.