Q3 Lab#1 Nitration of Benzoate FINAL.docx

The crude product was massed and then recrystallized

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filtered using a Buchner funnel to obtain a dry, white product. The crude product was massed and then recrystallized with hot methanol. Methanol (4mL) was heated to 40°C and then 5-10 drops were added to a beaker of product. Under gentle heat, the product dissolved and then after 5-10 minutes, it crystallized into small, white particles. The crystallized product was massed and then tested for melting point, an IR spectrum, and a NMR spectrum. Name Methyl Benzoate Nitric Acid (1:1 mix of H2SO4/HNO3)  Sulfuric Acid Methyl 3- Nitrobenzate Formula C 6 H 5 CO 2 CH 3 HNO 3 H 2 SO 4 C 8 H 7 NO 4 Molecular Weight 136.15 g/mol 63.01 g/mol 98.08 g/mol 181.15 g/mol Quantity (g, mL) 210  µ L 300  µ L 450 µ L 303g Millimoles 1.67 mmol 2.4 mmol --- 1.67 mmol Equivalents 1 1.44 --- 1 Density/mass % 1.08 g/mL 8M 0.791 g/mL 1.30 g/mL MP/BP Mp: -15 ° C Mp: -41.6 ° C Mp: 10 ° C Mp: 78-80 ° C
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Results Product: Methyl 3-Nitrobenzate Crude Yield (mass) .222g, 73% Final Yield (mass, %) .0796g, 26% Description (state, color) White, thin specks - crystally   Melting Point Range  81-83 ° C NMR sample (solvent) CDCl 3 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) 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) Discussion   Methyl 3-nitrobenzoate was successfully synthesized from methyl benzoate by an electrophilic aromatic substitution with nitric acid. Several spectroscopic techniques such as infrared spectroscopy,   1 H NMR, and melting point were utilized to characterize the product. The infrared spectrum exhibited 4 stretches over 3000
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