What would be the mechanism for the experiment below? PREPARATION OF PHENACETIN FROM ACETAMINOPHEN!INTRODUCTIONPhenacetin was one of the first synthetic analgesics, introduced in 1887 by Bayer. While itremained on the market for almost 100 years, it was later found to be carcinogenic, andhave kidney damaging properties. Its prolonged use was thought to be responsible for thedeath 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 fromacetaminophen utilizes a Williamson ether synthesis, one of the most common methodsemployed to prepare ethers. In this reaction, an alkoxide anion acts as a nucleophile in anSx2 process, displacing a leaving group from an electrophile.OHK₂00,As acetaminophen is a phenol, it is sufficiently acidic enough to be deprotonated bypotassium carbonate. The resulting phenoxide anion serves as the nucleophile in thedisplacement of iodine from sodoethane.PROCEDUREIn a 50 ml. round bottom flask, combine 8.6 mmol acetaminophen, 2.5 g potassiumcarbonate, and 15 ml. 2-butanone. Add 1.0 ml. iodoethane and a boiling chip. Attach acondenser and reflux for 1 hour. Allow the flask to cool slightly and gravity filter contentsinto a separatory funnel. Rinse the solids in the filter paper with 2x 5 ml. ether. Extractthe solution with 20 mL 5% aqueous NaOH and then 20 ml water. Transfer organic layerto 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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What would be the mechanism for the experiment below?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 63AP: As far back as the 16th century, South American Incas chewed the leaves of the coca bush,...

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