A Multioutcome Experiment for the Williamson Ether Synthesis

Williamson ether experiments are commonly performed by students in undergraduate organic chemistry instructional laboratory courses. In this multioutcome experiment, students were provided 4-bromophenol and one of three alkyl halides: 1-bromopentane, 1-bromobutane, or 1-bromo-3-methylbutane. The alkyl halides served as the unknown component of the experiment, and students were given these three as unknown candidates. After isolating the product from the reaction mixture, students analyzed their products using FT-IR and benchtop [superscript 1]H NMR spectroscopies. The experimental results herein summarize the inclusion of this experiment in the large enrollment second-semester organic chemistry laboratory course over four semesters.