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Abstract
Undergraduate organic chemistry laboratory courses across the United States complete similar experiments at various institutions. These experiments follow cookbook-style procedures and use known starting materials to synthesize known products. Students completing these experiments have little to no variation in their observations, results, data analysis, or reports, limiting opportunities for critical thinking. The use of multi-outcome experiments (MOEs) in organic chemistry requires critical thinking from students to identify the starting material and/or product for an experiment using spectroscopic analyses. The number of options for unknown starting materials generates student results that differ from student to student, providing more unique learning experiences and individualized lab reports. Herein are described a variety of MOEs for the undergraduate organic chemistry laboratory: a modified separation of a three-component mixture via acid-base extraction, an oxidation of secondary alcohols, a Williamson ether synthesis, a Fischer esterification, and a synthesis of azo dyes. MOEs such as these steer undergraduate organic chemistry laboratory courses away from cookbook reactions and more strongly reinforce lecture-learned concepts such as spectroscopic analyses.