Cyclopentadiene Recovery

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Maleic anhydride underwent the Dials-Alder reaction with distilled cyclopentadiene as the dienophile. The reaction was a cycloaddition which produced cis-Norbornene-5,6-endo-dicarboxylic Anhydride surface. (1) Product one had a mass of 9.351 grams and product two had a mass of 9.572 grams. The theoretical yield was found to be 10.047 grams, which makes the percent yield to be 93.07%. Melting Points were found to confirm the purity of the product. Product one had a melting point of 163.7-164.8°C. Product two had a melting point of 162.2-163.9°C. IR Spectroscopy (nujol) are carbonyl peaks (1773.4 cm-1), Sp3 C-H peaks (2921.5 cm-1), Sp2 C-H (3000 cm-1). The carbonyl peaks prove the presence of an acid anhydride. H’NMR (CDCL3) 6.287ppm (t, 2H), 3.674ppm (m, 2H), 3.483ppm (m, 2H), 1.697ppm (m, 2H). 13C NMR (CDCL3) 172.291, 135.913, 53.109, 47.572, 46.288. Next, hydrolysis of the anhydride took place. The anhydride was combined with distilled water in a 125 mL Erlenmeyer flask and heated. After twenty minutes the solid is partially dissolved and removed from the hot plate. The solution sits at room temperature for thirty minutes and a boiling chip is placed in the flask. Instantly crystals begin to form and flask is put in an ice bath. Vacuum filtration is preformed to collect the product and washed with cold water. Mass of the product was 3.329 g which comes out to be a 76.11% yield. The melting point of the product was 176.8-179.4°C. IR (nujol) 2500-3500 cm-1(-OH), 2922.8 cm-1 and 2853.8 cm-1 (Sp3 C-H); H1NMR (d6-DMSO) 11.487ppm (2, 0), 6.097ppm (M, 2H), 3.160 ppm (D, 2H), 2.995 ppm (S, 2H), 1.280 ppm (S, 2H); 13C NMR (d6-DMSO) 173.979 ppm, 135.199 ppm, 48.714 ppm, 48.269 ppm, 46.384 ppm. After hydrolysis the Fisher Esterification reaction is ran on the diacid. In a 25 mL round bottom flask the endo-diacid is mixed with methanol and concentrated sulfuric acid. A boiling chip is added to the flask and a reflux condenser is attached. The mixture...
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