Long lab - Multistep Synthesis Author: T.A: Forrest...

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Multistep Synthesis Author: T.A: Forrest Helfrich Date Performed: March19th, March 26 th Date Submitted: April 2nd Abstract: In the benzoin condensation of Benzaldehyde, .12g of benzoin was made. The melting point for benzoin was found to be 134 degrees C which was very close to the actual expected melting point. In the IR, an OH peak was found at 3430.68. The C=O peak was found at 1608.95 and the benzene ring was found at 1464.87. In the oxidation of Benzoin to Benzil, .006g of benzil was made. The IR showed a disappearance of the OH bond which was a good sign that the benzil was produced. It had C=O peak at 1700.03 and the benzene rings peak at 1465.19. In the synthesis of Tetraphenylcyclopentadienone, .412g of product was obtained and the melting point was at 222 degrees C. The IR spectrum showed a C=O peak at 1702.77 and the benzene rings at 1465.
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Introduction In this experiment we will be doing a multistep experiment to obtain tetraphenylcyclopentadienenone. An aldol condensation will be used in this multistep experiment. In an aldol condensation, an enoate ion reacts with a carbonyl compound to form a beta-hydroxyaldehyde. Then, a dehydration occurs in which it turns into a conjugated enone. This is done for aldehydes and ketones with an alpha hydrogen. But, if an alpha hydrogen is not present on the aldehyde or ketone, a aldol condensation will not occur. The first reaction mechanism that is going to be performed is the conjugation of benzaldehyde to benzoin. In this part of the experiment, an aldol condensation will not be used because it does not have the necessary alpha hydrogen needed to perform the condensation. In the benzoin condensation, a cyanohydrin will be made due to the CN- molecule attacking the carbonyl in benzaldehyde. A carbanion then attacks another benzaldehyde which results in the benzoin. Then benzoin will be conjugated into benzil. The last step in the experiment, a double aldol condensation and dehydration is performed. The results of this part of the experiment will be a tetraphenylcyclopentadienone. Benzoin Condensation of Benzaldehyde Substance MW MP BP d Safety Considerations benzaldehyde 106.13 -26 178.1 4.1
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thiamine 266.4 248 ethanol 46.06 158.8 351.6 0.79 flammable NaOH 39.99318 318 1390 2.1 chemical burns, flammable benzoin 212.25 137 344 1.31 nitric acid 63.01 -42 83 1.51 corrosive, cause burns benzil 210.23 94 346 1.23 KOH 56.1 406 1320 2.04 corrosive Materials Round-bottom flask Magnetic stirrer Benzaldehyde Vial Thiamine catalyst Ethanol NaOH
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Long lab - Multistep Synthesis Author: T.A: Forrest...

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