Tetraphenylcyclopentadienone Synthesis Essay

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The purpose of this lab was to prepare tetraphenylcyclopentadienone most commonly known as tetracyclone. This involved a 3-step synthesis over the course of 3 weeks. The first step was the preparation of benzoin, which was completed through self-condensation of benzaldehyde with thiamine used as the base catalyst of the reaction. The next step was the preparation of benzil from the oxidation reaction of benzoin with nitric acid. In the oxidation reaction, the alcohol functional group of benzoin was oxidized to form the carbonyl functional group of benzil, while the nitric acid was reduced into a mixture of nitrogen oxides that formed toxic brown fumes. The final step was the preparation of tetracyclone from the aldol condensation reaction of …show more content…
To ensure the reaction was complete the melting point was obtained and determined to be 128℃. The limiting reagent for this reaction was determined to be benzaldehyde as it was a 2: 1 ratio. Using the theoretical yield of 20.70 g, the percent yield was calculated to be 28.74 %. This could have been higher if the reflux was completed for 90 minutes like the procedure called for instead of 60 minutes. This could have influenced the amount of product obtained from the reflux. The second part of this multistep synthesis was to prepare Benzil from the reaction of Benzoin and HNO3. This was done through reflux, vacuum filtration and recrystallization techniques. The melting point was recorded to ensure the completion of this reaction. The melting point was determined to be 69℃. The limiting reagent for this reaction was determined to be benzoin. Using the theoretical yield of 5.89 g the percent yield was calculated to be 70.97%. While special care was taken to follow the procedure, the recrystallization of the crude benzil product was challenging because while scratching the flask with the mixture there were no crystals produced. This may have influenced the final amount of crude …show more content…
In the IR the first peak was a ketone functional group as indicated by a wavenumber of 1701 cm-1. The second peak was a phenyl functional group as indicated by a wavenumber of 1463 cm-1. The third prominent peak was an alkane functional group indicated by two different wavenumbers 2915 and 2850. Even though an IR proves to be helpful in determining the final product, in the case an IR proved otherwise as it did not help indicate the presence of the quantity for the phenyl functional group. The IR doesn’t differentiate different structures, so obtaining an IR for Benzil, Benzoin, and Tetracyclone would result in the same IR regardless that these products all have different

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