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 preparations 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 S<sub>N</sub>2 process, displacing a leaving group from an electrophile.
[Diagram here:
- Two chemical reaction diagrams are shown.
- The first diagram shows the transformation of acetaminophen into an anion with the aid of potassium carbonate.
- The second diagram illustrates the phenacetin formation, showing ethyl iodide reacting with the anion.
]
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 iodide 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 atop boiling dip. Attach a condenser. Cool flask and rinse solids from walls using pipet with 2 x 5mL ether. Filter mixture to remove alkali solid. Rinse the solids in the filter paper with 2 x 5 mL ether. Extract the filtrate 2 x 5 mL 1.5 M sodium hydroxide. Dry the organic extract over sodium sulfate in an Erlenmeyer flask and dry with magnesium sulfate and decantate the dried solution. Recrystallize the crude product from a minimum amount of acetone. Collect the crystals.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F97a0b142-fcf0-4b7b-946c-b5d706c6bb8f%2F12f85e5c-f0c8-46ce-961c-aa5d56b36349%2Fun8d5yl_processed.jpeg&w=3840&q=75)
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 preparations 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 S<sub>N</sub>2 process, displacing a leaving group from an electrophile.
[Diagram here:
- Two chemical reaction diagrams are shown.
- The first diagram shows the transformation of acetaminophen into an anion with the aid of potassium carbonate.
- The second diagram illustrates the phenacetin formation, showing ethyl iodide reacting with the anion.
]
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 iodide 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 atop boiling dip. Attach a condenser. Cool flask and rinse solids from walls using pipet with 2 x 5mL ether. Filter mixture to remove alkali solid. Rinse the solids in the filter paper with 2 x 5 mL ether. Extract the filtrate 2 x 5 mL 1.5 M sodium hydroxide. Dry the organic extract over sodium sulfate in an Erlenmeyer flask and dry with magnesium sulfate and decantate the dried solution. Recrystallize the crude product from a minimum amount of acetone. Collect the crystals.
Expert Solution
Step 1
We have to give the mechanism of the given reaction.
Concept: We need to know about the substitution binuclear reaction (SN2).
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