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262-8 - Anusha Vadlamudi TA Lindsay Aldridge Chem 262 L 401...

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Anusha Vadlamudi TA: Lindsay Aldridge Chem 262 L 401; Rm: 300 Experiment VIII: Electrophillic Aromatic Substitution: Nitration of 4- methylacetanilide An inverted glass funnel was placed over the mouth of the Erlenmeyer flask and connected to the aspirator. To a dry 10 mL Erlenmeyer flask with a magnetic stir bar, 2 mL of 70% nitric acid were added. Then, 398 mg of 4-methylacetanilide was added to the flask. The solution was continued to stir for 20 minutes. The resulting orange mixture was poured into 10 mL of ice water and the yellow product was filtered quickly by suction filtration using a Hirsch funnel. Ice-cold water of 2-mL portions was used five times to wash the product. The solid was let to stand for 5 minutes. The crude product appeared neon yellow and weighed to be 505 mg. The percent yield came out to be 96.93%, which was pretty high. Of this, 106 mg was saved for experiment 9, a small amount was saved for TLC, and the remaining was recrystallized. After recrystallization, the neon yellow product appeared fluffy and weighed 134 mg. For TLC analysis, a small
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