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What would be the mechanism for the experiment below?

What would be the mechanism for the experiment below?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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What would be the mechanism 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 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 utilizes 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 Sx2 process, displacing a leaving group from an electrophile. OH K₂00, As 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 sodoethane. 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 a boiling chip. Attach a condenser and reflux for 1 hour. Allow the flask to cool slightly and gravity filter contents into a separatory funnel. Rinse the solids in the filter paper with 2x 5 ml. ether. Extract the solution with 20 mL 5% aqueous NaOH and then 20 ml water. Transfer organic layer to an Erlenmeyer flask and dry with magnesium sulfate and concentrate the dried solution. Recrystallize the crude product from a minimum amount of water. Collect the crystals,
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 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 utilizes 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 Sx2 process, displacing a leaving group from an electrophile. OH K₂00, As 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 sodoethane. 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 a boiling chip. Attach a condenser and reflux for 1 hour. Allow the flask to cool slightly and gravity filter contents into a separatory funnel. Rinse the solids in the filter paper with 2x 5 ml. ether. Extract the solution with 20 mL 5% aqueous NaOH and then 20 ml water. Transfer organic layer to an Erlenmeyer flask and dry with magnesium sulfate and concentrate the dried solution. Recrystallize the crude product from a minimum amount of water. Collect the crystals,
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