Synthesis Of Cyclopentadienone

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The purpose of this experiment was to use aldol condensation methods to synthesize colored cyclopentadienone and then UV/VIS spectrophotometry to characterize the dienone structure synthesized. The information gathered from the UV/VIS analysis was then compared to a computer model of the desired product to analyze the optimal 3D structure of the dienone. The base catalyzed condensation reaction was used to form the product for analysis, followed by vacuum filtration to recover the product. Both a melting point analysis and a UV/VIS analysis were used to analyze the composition of the obtained product. Finally, the computer model was examined to learn about the optimal angles and strain within the molecule.
The dibenzylketone, 1,3-diphenyl-2-propanone,
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This is due to the repulsion from similarly charged atoms along with the steric hindrance caused by the size and quantity of benzene rings on the compound. The rotational direction of the phenyls depends upon the side that is being analyzed. A 180-degree flip will cause the rotation to flip from counterclockwise to clockwise or vice versa. When the compound is aligned in a way that it can be rotated clockwise it behaves in a way that mimics a propeller. It can be noted that if the enantiomer of the compound analyzed was what was to be analyzed every chiral center in the compound would display the opposite rotation, causing the compound to behave in a completely contradictory way to what was analyzed in the compound below. It was observed during analysis of the compound that the phenyl group nearest the carbonyl carbon was less bent off the normal axis than those that were further away from the carbonyl carbon. This is likely due to the negative charge of the electrons on the double bonded oxygen displaying a stronger pull on the closest phenyl than the repulsion of the surrounding phenyls can have in comparison to the phenyl that is much further away from the double bonded O where the surrounding phenyls can have a much stronger effect than the distant C=O

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