Post Lab 10 Discussion

7 based on the spectral data of the concentrated

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cannot be identified from the information obtained so far. 7. Based on the spectral data of the concentrated reaction mixture, the accuracy of the percent yield of the product alkyne cannot be determine, since no product was produced. The actual yield is also not possible to calculate based on our percent composition. The theoretical yield was 532 mg. 8. Based on the results, many things could have been done differently to improve the yield of product. Instead of using ammonium and amides, which were poor acids, a more sterically hindered acid should have been used, such as tert-butoxide. It would be better to have a strong base that is non-nucleophilic, allowing for the reaction to take place, but keeping the base from reacting with the reagents. Conclusion: Overall, this experiment did not go as planned and was very unsuccessful. The main objective of this lab was to start with two staring materials, benzyl bromide and phenyl acetylene, to react together and form an alkyne. However, the alkyne product that was expected was not formed. Instead the product formed was called stilbene, which was an alkene instead of an alkyne, and had one less carbon bond. The other carbon side products that were formed were phenylethyne and an amine with three phenyls attached. There were also reduced products that formed on the side. Many things could have gone wrong with this procedure, but there isn’t a clear answer as to what reaction actually took place in forming this alkene.
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