. Williamson Ether Synthesis Questions for lab , Synthesize phenacetin from acetaminophen (Tylenol) via a Williamson ether synthesis.   a.Find the missing reagent: CH3CH2OH +? → C2H5OC2H5     H2SO4,

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
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1. Williamson Ether Synthesis Questions for lab , Synthesize phenacetin from acetaminophen (Tylenol) via a Williamson ether synthesis.

 

a.Find the missing reagent:
CH3CH2OH +? → C2H5OC2H5

   

H2SO4,

   

 H2O

   

HNO3,

   

H2CO3

   

b.What is the nucleophile in this reaction?

   

H2O

   

Nu-

   

RO-

   

ROH

c.If you wanted to prepare Guaifenesin (present in OTC cough meds), choose the alcohol you would start with?

   

2 methoxy benzoinc acid

   

2-methoxy benzaldehyde

   

2-methoxyphenol

   

2 methoxy anisole

d.What was the mechanism of the reaction you used to prepare the ether?

   

SN1

   

SN2

   

E1

   

E2

e.The reaction given below is known as by which o the following reaction?

C2H5ONa+IC2H5→C2H5OC2H5+NaI

   

Oxidation reaction

   

Williamson reduction reaction

   

Williamson ether synthesis

   

Wittig synthesis

f.Chloroethane reacts with X to form diethyl ether. What is X?

   

Sodium carbonate

   

Sodium ethoxide

   

Sulfuric acid

   

Sodium chloride

j.Which of the following will facilitate this reaction?

   

Strong nucleophile

   

slow leaving group

   

Bulky groups

   

tertiary alkyl halide

k.What is the rate determining step of this reaction?

   

Formation of carbocation

   

Formation of the transition state

   

The addition of water

   

The isolation of the ether

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