Q3 Lab#1 Nitration of Benzoate FINAL.docx

The infrared spectrum exhibited 4 stretches over 3000

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melting point were utilized to characterize the product. The infrared spectrum exhibited 4 stretches over 3000 cm -1  and 1 stretch under 3000 cm -1 , indicating the presence of sp2 C-H bonds and sp3 C-H bonds, respectively. The stretch at 1717.34 cm -1  shows an ester carbonyl that was also present in the reactant, signifying that no side reaction occurred with that carbonyl. More significantly, there is a N-O stretch found at 1527.57 cm -1   that proves the successful substitution of the nitro group. These functional groups interpreted from the IR correctly identify with methyl 3-nitrobenzoate.   1 H NMR also confirms the formation of methyl 3-nitrobenzoate by providing information on the structure of the product. The peaks at 7.24ppm, 3.47 ppm, and 1.38 ppm correspond with CHCl 3 , methanol, and water, respectively. The multiplicities and coupling constants of the product were used to determine the regiochemistry of the product. The analysis of the doublet of doublets at Hb/Hd and the doublet of doublet of doublets at Ha/Hc and their chemical shifts led to the conclusion that the nitrate substituted at the meta position. The integration values of 1 for those hydrogen’s further confirmed the analysis. The chemical shift at 3.97 ppm was seen to be a singlet with an integration of 3 that corresponded with the methyl group. The experiment achieved a crude yield of 72% and a final yield of 26% after recrystallization.
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