Please correct answer and don't use hand raiting 3. Analysis Questions:a) Mechanism of Reaction: The first step is a deprotonation of the -O-H group ofacetaminophen by the hydroxide. Then, when the ethyl iodide is added, the anion ofacetaminophen 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 comoccurring.b) A student misread the instructions and added the chemicals out of order: they first refluxedthe sodium hydroxide (in ethanol) with the ethyl iodide for 15 minutes, and then later addedthe 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 wasthis the case? What happened instead?

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Answered: 3. Analysis Questions: a) Mechanism of…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 68AP: Fill in the missing reagents a-e in the following scheme:

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Williamson Ether Synthesis of Phenacetin Background: Synthesize phenacetin from acetaminophen (Tylenol) via a Williamson ether synthesis.The Williamson ether synthesis is one of the simplest methods used to make ethers. The reaction is named after Alexander Williamson, who discovered the reaction in 1850. In this reaction, an alkoxide anion reacts with an alkyl halide via a substitution reaction. RO-Na+ + R` – X → R-O-R` + NaX Alkoxides are strong nucleophiles that tend to react via an SN2 mechanism. As a result, the reaction works best with primary alkyl halides. In a traditional Williamson ether synthesis, the alkoxide is generated by reacting sodium hydride (NaH) with an alcohol. ROH + NaH → RO-Na+ + H2 While this reaction is very efficient, it does pose a fire hazard, as it is possible for hydrogen gas to ignite. In this lab, the alkoxide will be created using sodium hydroxide (NaOH). This is a much safer option, eliminating a…
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1. Br₂, PBrg 2. H₂O H₂C OH H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br₂ reacts in an α- substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H3C :0: :0::Br: Br Br H3C CO-P H Br Br
Fill in the missing reagents a-e in the following scheme:
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