A microscale experiment is presented in which cyclohexene is dihydroxylated under three sets of conditions: epoxidation-hydrolysis, permanganate oxidation, and the Woodward dihydroxylation. The products of the reactions are determined by the use of thin-layer chromatography. Teams of students are presented with proposed mechanisms for each dihydroxylation and are asked to evaluate them in light of data collected during the experiment. Both the timing of the lab in relation to the classroom curriculum and alternative applications of the lab are discussed. (Contains 1 figure and 2 notes.)