Nitration Of Bromobenzene Lab Report

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This experiment was performed in order to demonstrate the principles of nitration through electrophilic aromatic substitution. It also examined the effects of bromine on an aromatic ring, ortho-para vs. meso directing. The second experiment was performed to compare the reaction rates of electrophilic aromatic bromination with different arenes.

Data and Results In the gas chromatogram, there are two large peaks. The first peak at 0.653 minutes with an area of 133,352 uV per second, 31.95% of the total area. The second peak is at 0.883 minutes with an area of 281,798 uV per second, 67.52% of the total area. There were also two small peaks at 0.482 minutes and 0.746 minutes. These peaks comprised 0.14% and 0.39% of the area respectively. When comparing the relative rates of reaction, the fastest reaction occurred with phenol. The second fastest was
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It would be expected that the larger peak would be the first peak to elute because the para product, 4-bromonitrobenzene, is less polar and would thus be less attracted to the column. However, in the gaschromatography data, the larger peak was second and had a retention time of 0.88 minutes, which is much less than the expected retention time of 20.88 minutes for 4-bromonitrobenzene. It would be expected that the smaller peak would be second because the ortho product, 2-bromonitrobenzene, is more polar and would thus be more attracted to the column. However, the smaller peak was first and had a retention time of 0.65 minutes, which is much less than the expected retention time of 2-bromonitrobenzene at 21.18 minutes. The two small peaks were likely the initial reactant and the meso product, 3-bromonitrobenzene, which is produced in very small quantities. However, the area distribution of 67% to 32% was very near the expected distribution of 62% to 37%. These errors may have been due to problems with the gas

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