At its core, pinacol rearrangement is a chemical reaction that converts a 1,2-diol to a carbonyl. During this reaction, the acid is used as a catalyst to dehydrate glycols, converting them to an aldehyde or a ketone. In this case, sulfuric acid was a catalyst with a volume of 3.5mL and a concentration of 0.0356mol. After the reaction, the pinacolone mixture resulted in a weight of 1.1188g, suggesting 1.7g or 66 percent yield. These results are lower than expected, as two reasons might be behind this small yield. The first possible reason is that product might have been lost during the washing or purification process. The second cause could be that the product did not fully react. Thus, the reaction could have been improved by waiting longer for it to complete or by using a higher concentration of sulfuric acid to speed up and boost it. Another part of chemical reaction success is the temperature of the reaction. Therefore, the room temperature might have been a little bit low for the reaction, as it occurred at ambient temperature levels. Only two of the possible three IR peaks were recorded: the first ketone peak (1710-1720) and the second – that of the O-H bond in alcohol (3230-3500). The second peak suggests the incomplete nature of the reaction, as it is safe to assume it is the reason for the low yield.
Annotated Bibliography
Gebhart, H. J.; Adams, K. H. Kinetics and Mechanism of the Pinacol Rearrangement. i. the Perchloric Acid-Catalyzed Rearrangement of Benzopinacol and of Tetraphenylethylene Oxide in Acetic Acid Solution1. Journal of the American Chemical Society 1954, 76 (15), 3925–3930.
This source describes the mechanisms and kinetics of pinacol rearrangement reaction on the example of perchloric acid-catalyzed rearrangement of benzopinacol and of tetraphenylethylene oxide in acetic acid solution. It explores this reaction using two distinct kinetic routes. The first route involves the immediate formation of tetraphenylethylene oxide. On the other hand, during the second route, the ketone in the concentration of 80 percent is formed at 75 degrees. Analyzing these reactions, the conclusion is that the formation of the intermediate product is followed by the ionization of the oxonium complex. This suggests classical carbonium ion as intermediate, as the entropy values are high. For this case, this means that entropy was low to form carbonium ions to complete the reaction.