3. Analysis Questions: a) Mechanism of Reaction: The first step is a deprotonation of the -O-H group of acetaminophen by the hydroxide. Then, when the ethyl iodide is added, the anion of acetaminophen does an SN2 attack of the ethyl iodide to create a new ether bond. Explain why this reaction promotes 100% SN2 product while excluding any E2 reaction com occurring. b) A student misread the instructions and added the chemicals out of order: they first refluxed the sodium hydroxide (in ethanol) with the ethyl iodide for 15 minutes, and then later added the acetaminophen and continued to heat for 20 min. After isolating the so-called "product", the TLC showed that it was all still acetaminophen. No phenacetin was produced. Why was this the case? What happened instead?
3. Analysis Questions: a) Mechanism of Reaction: The first step is a deprotonation of the -O-H group of acetaminophen by the hydroxide. Then, when the ethyl iodide is added, the anion of acetaminophen does an SN2 attack of the ethyl iodide to create a new ether bond. Explain why this reaction promotes 100% SN2 product while excluding any E2 reaction com occurring. b) A student misread the instructions and added the chemicals out of order: they first refluxed the sodium hydroxide (in ethanol) with the ethyl iodide for 15 minutes, and then later added the acetaminophen and continued to heat for 20 min. After isolating the so-called "product", the TLC showed that it was all still acetaminophen. No phenacetin was produced. Why was this the case? What happened instead?
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter23: Addition To A Carbonyl
Section: Chapter Questions
Problem 42CTQ
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Please correct answer and don't use hand raiting
Transcribed Image Text:3. Analysis Questions:
a) Mechanism of Reaction: The first step is a deprotonation of the -O-H group of
acetaminophen by the hydroxide. Then, when the ethyl iodide is added, the anion of
acetaminophen does an SN2 attack of the ethyl iodide to create a new ether bond.
Explain why this reaction promotes 100% SN2 product while excluding any E2 reaction com
occurring.
b) A student misread the instructions and added the chemicals out of order: they first refluxed
the sodium hydroxide (in ethanol) with the ethyl iodide for 15 minutes, and then later added
the acetaminophen and continued to heat for 20 min. After isolating the so-called "product",
the TLC showed that it was all still acetaminophen. No phenacetin was produced. Why was
this the case? What happened instead?
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