The pinacol rearrangement constitutes the dehydration of pinacol and the stabilization of carbocation by the shift of methyl. The mechanism of pinacol rearrangement follows the S N 1 reaction mechanism with pinacol as a limiting reagent. The mechanism of the pinacol rearrangement commences with the protonation of one of the two –OH groups. Anslyn and Dougherty explain that the protons derived from the concentrated sulfuric acid get attracted to the lone pairs of electrons on one of the –OH group in the pinacol (675). The interaction of the proton with the –OH group leads to the formation of oxonium ion (-OH 2 + ). The oxonium ion leaves the pinacol and creates a tertiary carbocation that causes a methyl shift in a manner that stabilizes it (Anslyn and Dougherty 675). The methyl shift culminates in the formation of pinacolone (ketone). Figure 1 below demonstrated the mechanism of pinacol rearrangement. Figure 1: Mechanism of pinacol rearrangement Evaluation of the experimental procedure shows that it was performed successfully as the pinacol rearrangement happened as expected. Comparative analysis of the theoretical yield and the actual yield of the experiment show a disparity. Starting with the 3 g of the pinacol, which is the limiting reagent, the theoretical yield of pinacolone could be 2.604 g. However, the actual yield obtained from 3 g of pinacol is 1.5 g, which is 57.6% of the theoretical yield. Therefore, the experiment managed to synthesize pinacolone, although constituting 57.6% of the theoretical yield. The low yield emanated from diverse sources of errors that are inherent in the experimental procedure. A feasible source of error could be an incomplete conversion of pinacol. Other possible sources of errors could be inaccurate pipetting of aqueous layer resulting in the loss of pinacolone and evaporation during the distillation process. Sulfuric acid was used in the experiment to provide hydrogen ions (H + ) for the pinacol rearrangement to occur. As -OH group is bad leaving group, its protonation results in the formation of oxonium ion (-OH 2 + ), which is a good leaving group (Anslyn and Dougherty 675). Fundamentally, part of the reaction of pinacol rearrangement is the dehydration. Sulfuric acid dehydrates pinacol and creates tertiary carbocation, which triggers a shift in methyl group from the primary to the tertiary position. Figure 2: Dehydration effect of concentrated sulfuric acid Simple distillation was used in the separation of water and pinacolone. The simple distillation applies to the separation of two or more liquids, which have a considerable difference in boiling points (Diwekar 3). The simple distillation aimed to separate water and pinacolone from the reaction contents containing traces of pinacol and sulfuric acid. Water and pinacolone have boiling points of 100°C and 106°C respectively. As the boiling point of sulfuric acid is 290°C while that of pinacol is 172°C, these boiling points are considerably higher than that of water and pinacolone, and thus, a simple distillation procedure separates them effectively. The distillation process stopped at 100°C because water and pinacolone have close boiling points. Raoult’s law explains why the distillation process was stopp