Pinacol Was Mixed With Sulfuric Acid

In this experiment, pinacol was mixed with sulfuric acid, which protonated the pinacol, allowing it to form a better leaving group. Water is the leaving group off of the pinacol and the pinacol becomes a carbocation. The carbocation that is formed is a secondary carbocation so, rearrangement occurs. A methyl shift happens to form a tertiary carbocation, which is more stable than a secondary carbocation. Then, the remaining oxygen forms a double bond causing it to have a positive charge; allowing the carbon that had a positive charge to have a full octet and to be neutral. Then, the sodium bicarbonate deprotonates the oxygen, which makes the oxygen neutral and forms pinacolone as the product.

A technique that was used in this experiment was a distillation, which is a method for separating mixtures, in this case, based on boiling points. Since the components used (water and pinacol solution) are immiscible, each component acts independently, the boiling point of the mixture should be below the boiling point of the lowest boiling component.2 The boiling point of water is 100C while the boiling point of pinacol is 106C, so the distillation was stopped at 100C. An aqueous layer and a pinacolone layer are formed. The bottom layer is the aqueous layer because the density of pinacolone is 0.801 g/mL while …show more content…
Human errors have impacted the amount of pinacolone formed because the percent yield was not a 100%. The distillation could have been stopped too early, allowing for a loss of product. Some of the product was lost when the two layers were separated because some of the organic layer could have been removed along with the aqueous layer. Also, the formation of the carbonations from secondary to tertiary could have impacted the reaction because the unstable carbocation would not form the