Brittney Brown Due: 10-29-2009 Title: Multi-step synthesis of 4-bromo-2chloroacetanilide Lab Partner: Chelsea Searels The purpose of this lab was to covert 4-bromo-2-chloroacetanilide from aniline through a series of steps being attentive of the percent yield. Experimental infrared spectroscopes and melting points were obtained of the products for confirmation of the desired products. Experimental Details: Table 1. List of Reagents/Reactants Substance Amount Molecular Weight (g/mol) mmol Density (g/ mL) Boiling/ Melting Point (°C) Week One: Preparation of Aniline from Nitrobenzene Granulated tin 6.096g 118.71 50.7 7.287 MP=232°C Nitrobenzene 2.6mL 123.06 25.3 1.199 BP= 210.9°C HCl 13mL 36.46 420 1.18 BP= 110°C Sodium hydroxide 12mL 39.997 639 2.13 MP= 323°C Week Two: Acetanilide from Aniline and 4-bromoacetanilide from Acetanilide Recovered aniline Stock aniline 0.3g 2.0mL 93.13 25.23 1.0217 BP=184.83°C HCl 2.1mL 34.46 67.96 1.18 BP=110°C Sodium acetate 2.484g 82.02 30.29 1.528 MP= 324°C Acetic anhydride 2.8mL 102.09 24.87 1.089 BP=39.8°C Ethanol 3.3mL 46.07 90.8 0.789 BP=78.4°C Bromine 1mL 70 44.33 3.1028 BP= 58.78°C 1
Week Three: 4-bromo-2-chloroacetanilide from 4-bromoacetanilide Suspeneded 4-bromoacetanilide 2.00g 214.06 9.3 1.717 166-170°C HCl 6mL 36.46 139 1.18 BP= 110°C Acetic acid 7mL 60.05 111.12 1.049 118.1°C NaClO3 0.501g 106.5 4.6 2.5 MP= 448°C The mutli-step synthesis was completed over a course of three weeks. In the first week, aniline was prepared from nitrobenzene by adding 6.094g 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 0.3g of aniline was collected. The aniline was noted
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