Due to a lack of time and, thus, an inability to present every possibility in a chemical reaction, organic chemistry professors tend to present each reaction with a single outcome. In practice, this is clearly not the case. A first-semester, three-week laboratory experiment designed for undergraduate organic chemistry students is described in which students carry out the hydration of a monosubstituted alkene via two different reactions, a hydroboration/oxidation and an oxymercuration/demercuration, in the first two laboratory periods, and analyze the resulting product mixtures in the third week via gas chromatography (GC). Students gain hands-on experience with the GC instrument and compare the results of the two reaction types. Both reactions are carried out on the same alkene starting material, and the ratios of the primary alcohol (anti-Markovnikov) and secondary alcohol (Markovnikov) products formed in each reaction are calculated. Students write a formal report and discuss the regiochemistry of the reactions, identifying each reaction as either regiospecific or regioselective, depending upon their GC results and mechanistic interpretation.