Wittig Reaction Cinnamaldehyde

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The overall objective of this experiment was to perform a Wittig reaction from creating an ylide and mixing it with a carbonyl (C=O) compound, cinnamaldehyde. The completion of the reaction was confirmed ultimately from the initial TLC analysis. Since TLC separates the components of the spotted material, as long as the retention factor values were different for cinnamaldehyde, the starting reagent, and the product(s), it was evident that some of the reaction had gone to completion. However, as seen in Figure 3, there was some blurred area between the product spots. This indicated that there still existed some impurities, most likely the starting reagent, which was affecting the movement of the compounds through the solvent, petroleum …show more content…

After performing the second TLC analysis (Figure 4), it was apparent that the product had purified because of the separation from the starting spot, unlike Figure 3. In addition, there was only spot that could be seen on the final TLC, indicating that only one isomer formed. Since (E,E) is the more stable isomer due to a less steric hindrance relative to the (E,Z) isomer, it can be inferred that (E,E) 1,4-Diphenyl-1,3-butadiene was the sole product. The proton NMR also confirmed that only (E,E) 1,4-Diphenyl-1,3-butadiene formed; based on literature values, the (E,E) isomer has peaks between 6.6-7.0 ppm for vinyl protons and 7.2-7.5 ppm for the phenyl protons. Likewise, the (E,Z) isomer has vinyl proton peaks at 6.2-6.5 ppm and 6.7-6.9 ppm in addition to the phenyl protons. The H NMR in Figure 5 shows multiplets only after 6.5 ppm, again confirming that only (E,E) 1,4-Diphenyl-1,3-butadiene formed. In addition, the coupling constant J of the (E,E) isomer is around 14-15 Hz, while for the (E,Z) isomer it is 11-12 Hz. Based on the NMR in Figure 5, the coupling constant is 15.15 Hz, complementing the production of (E,E)

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