Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Question

What would be the reaction for the experiment below 

**Preparation of Phenacetin From Acetaminophen** **Introduction** Phenacetin was one of the first synthetic analgesics, introduced in 1887 by Bayer. While it remained on the market for almost 100 years, it was later found to be carcinogenic, and have kidney damaging properties. Its prolonged use was even thought to be responsible for the death of Howard Hughes, one of the most financially successful individuals of his time. While we would not want to take the drug today, the preparation of phenacetin from acetaminophen illustrates a Williamson ether synthesis, one of the most common methods employed to prepare ethers. In this reaction, an alkoxide anion acts as a nucleophile in an SN2 process, displacing a leaving group from an electrophile. **Chemical Reaction Diagram:** 1. Acetaminophen (shown with a benzene ring and functional groups) reacts with potassium carbonate (K₂CO₃) in an SN2 process. 2. Iodine group (I) is displaced from iodoethane, forming phenacetin. An acetaminophen is a phenol, it is sufficiently acidic enough to be deprotonated by potassium carbonate. The resulting phenoxide anion serves as the nucleophile in the displacement of iodine from iodoethane. **Procedure** In a 50 mL round bottom flask, combine 8.6 mmol acetaminophen, 2.5 g potassium carbonate, and 15 mL 2-butanone. Add 1.0 mL iodoethane and warm the solution on a heating mantle to reflux for 45 minutes. Allow the mixture to cool and then pour the reaction mixture into 75 mL of ice-cold water. Rinse the solids on the filter paper with 2 x 5 mL ether. Extract the ethereal layer four times with 5 mL portions of 5% aqueous sodium hydroxide solution, dry with an EnlitenHV flask and dry with magnesium sulfate and recrystallize the dried solid. Recrystallize the crude product from a minimum amount of solvent. Collect the crystals.
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Transcribed Image Text:**Preparation of Phenacetin From Acetaminophen** **Introduction** Phenacetin was one of the first synthetic analgesics, introduced in 1887 by Bayer. While it remained on the market for almost 100 years, it was later found to be carcinogenic, and have kidney damaging properties. Its prolonged use was even thought to be responsible for the death of Howard Hughes, one of the most financially successful individuals of his time. While we would not want to take the drug today, the preparation of phenacetin from acetaminophen illustrates a Williamson ether synthesis, one of the most common methods employed to prepare ethers. In this reaction, an alkoxide anion acts as a nucleophile in an SN2 process, displacing a leaving group from an electrophile. **Chemical Reaction Diagram:** 1. Acetaminophen (shown with a benzene ring and functional groups) reacts with potassium carbonate (K₂CO₃) in an SN2 process. 2. Iodine group (I) is displaced from iodoethane, forming phenacetin. An acetaminophen is a phenol, it is sufficiently acidic enough to be deprotonated by potassium carbonate. The resulting phenoxide anion serves as the nucleophile in the displacement of iodine from iodoethane. **Procedure** In a 50 mL round bottom flask, combine 8.6 mmol acetaminophen, 2.5 g potassium carbonate, and 15 mL 2-butanone. Add 1.0 mL iodoethane and warm the solution on a heating mantle to reflux for 45 minutes. Allow the mixture to cool and then pour the reaction mixture into 75 mL of ice-cold water. Rinse the solids on the filter paper with 2 x 5 mL ether. Extract the ethereal layer four times with 5 mL portions of 5% aqueous sodium hydroxide solution, dry with an EnlitenHV flask and dry with magnesium sulfate and recrystallize the dried solid. Recrystallize the crude product from a minimum amount of solvent. Collect the crystals.
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