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SCAN0004 - The mutli—step synthesis was completed over a...

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Unformatted text preview: The mutli—step synthesis was completed over a course of three weeks. In the first week, aniline was prepared from nitrobenzene by adding 6.0949 of granulated tin combined with 2.6mL of nitrobenzene in a 100—mL boiling flask. An ice bath made at 0°C and 13mL of HCl was added to the solution. A thermometer was inserted and the solution was stirred, maintaining a temperature of between 55 and 60°C. After 15 minutes, the mixture was heated on a reflux to ensure the completion of the reaction. Only 0.39 of aniline was collected. The aniline was noted as orange oil droplets suspended in the solution. For the second week, the synthesis continued in preparing acetanilide from aniline and 4-bromoacetanilide from acetanilide. The recovered aniline was mixed with 2mL of stock aniline to perform the experiment. About 50mL of water and 2mL of HCI was added to the aniline. A solution of 2.8mL of sodium acetate and 15 mL of water was prepared. To the aniline hydrochloride solution, 2.8mL of acetic anhydride was added followed by the solution of sodium acetate. The mixture was swirled for about 5 minutes then cooled in an ice bath. The precipitate was filtered and weighed. Next, 2.59 of the recovered product was added to 10mL of glacial acetic acid and stirred. Then, a solution of 1.04mL of bromine and 2mL of glacial acetic acid added. The mixture was stirred for 5 minutes while slowly adding 80mL of water. Enough sodium bisulfate was added to discharge the yellow color. The product was recrystallized by adding ethanol. The product was filtered and rinsed with water. Finally in the last week, 4-bromo-2-chloroacetanilide was prepared from 4- bromoacetanilide by weighing out 2.009 of 4—bromoacetanilide to suspend in 6mL of HCI and 7mL of acetic acid. The solution was heated on a hot plate until the solid was completely dissolved then cooled in an ice bath (0°C). A solution of 0.5009 of sodium chlorate and 1.5mL of water was added under the hood. The solution was allowed to stand for an hour. The solution was filter and the product collected and weighed (1). An IR was obtained for the products (4— bromo—2-chloroacetaniIide, 4-bromoacetanilide, and acetanilide). Data: Table 2. Data collected Mass of product (aniline) Mass of product: (Acetanilide) (4—bromoacetanilide) Mass of product (4-br0mo—2- chloroacetanilid_eL Melting Points for product acetanilide 2.9059 3.6789 1 .3099 1) 113-116°C 2 114-118°C Melting Points for product (4-bromoacetanilide) Melting Point for product 4-bromo—2-chIoroacetanilide Percent Yield (aniline Percent Yield: 1) 164-167°C 2 165-171°C 1) 148-150°C 2 149-153°C 13% (Acetanilide) 73% (4-bromoacetanilide) 89.1% Percent Yield (4-bromo-2- 56.4% chloroacetanilide) Overall Percent Yield 4.8% ...
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