Electrophilic Aromatic Substitution Reaction Lab Report

The purpose of this experiment was to learn about the electrophilic aromatic substitution reactions that take place on benzene, and how the presence of substituents in the ring affect the orientation of the incoming electrophile. Using acetanilide, as the starting material, glacial acetic acid, sulfuric acid, and nitric acid were mixed and stirred to produce p-nitroacetanilide. In a 125 mL Erlenmeyer flask, 3.305 g of acetanilide were allowed to mix with 5.0 mL of glacial acetic acid. This mixture was warmed in a hot plate with constantly stirring at a lukewarm temperature so as to avoid excess heating. If this happens, the mixture boils and it would be necessary to start the experiment all over again. After obtaining an homogeneous mixture, the flask was placed in an ice bath during five minutes next to a graduated cylinder containing 5.0 mL of concentrated sulfuric acid. The temperature of the ice bath was recorded to be 1.1 °C. Likewise, a second graduated cylinder containing 1.8 mL of nitric acid and 2.5 mL of sulfuric acid was immersed in the cold ice bath to keep the three different solutions at the same temperature.
Thereafter, the cold 5.0 mL of H2SO4 were added to the erlenmeyer flask containing the acetanilide solution, which remained in the cold water for approximately another 4 minutes. The next step

Nonetheless, the light yellow solid was purified by using the recrystallization technique. The formation of o-nitroacetanilide is inevitable and in order to eliminate it, 95% ethanol is used as the solvent of choice. The ortho isomer is soluble in the cold alcohol solution whereas p-nitroacetanilide in insoluble. As a result, the ortho isomer remains in the liquid solution and the final product, the p-nitroacetanilide is isolated with a final vacuum