Q3 Lab#1 Nitration of Benzoate FINAL.docx

The experiment achieved a crude yield of 72 and a

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the methyl group. The experiment achieved a crude yield of 72% and a final yield of 26% after recrystallization. The significant discrepancy can be attributed to the impurities in the raw product that was filtered out as a result of the crystallization in hot methanol. No side products were observed in the reaction; however, if proper methods were used, better yields would have been observed. The literature melting point for methyl 3- nitrobenzoate is 78-80 ° C which corresponds very closely to the experimental value of 81-83 ° C, providing further evidence on the identification of the product. Under consideration of the IR spectrum, NMR spectrum, and melting point, the product can be finalized as methyl 3-nitrobenzoate.    Citations –  For the melting point of Methyl 3-nitrobenzoate: 
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http://pubchem.ncbi.nlm.nih.gov/compound/Methyl_3-nitrobenzoate NMR 1 H NMR (400 MHz, chloroform- d ) δ 8.85 (dd, 1.9, 1.8 Hz, 1H, d), 8.40 (ddd, 8.2, 2.4, 1.2 Hz, 1H, a), 8.35 (ddd, 7.8, 1.4, 1.4 Hz, 1H, c), 7.64 (dd, 8.0, 7.9 Hz, 1H, b), 3.97 (s, 3H, e) IR SPECTRUM   FT IR (diamond anvil, neat) 3101.79, 3094.19, 3083.52, 3019.32 cm -1 (sp2 C-H stretch), 2963.70 (sp3 C-H stretch), 1717.34 (C=O stretch, ester), 1527.57 (N-O stretch, nitro) Hd Ha Hc Hb He
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