Make an electron-flow-mechanism for this synthetic scheme. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shows. (BENZENE -> 2-ACETOXYBENZOIC ACID or ASPIRIN)

Make an electron-flow-mechanism for this synthetic scheme. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shows. (BENZENE -> 2-ACETOXYBENZOIC ACID or ASPIRIN)

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.68P: Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this...

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Question

Make an electron-flow-mechanism for this synthetic scheme. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shows. (BENZENE -> 2-ACETOXYBENZOIC ACID or ASPIRIN)

Kolbe-Schmidt
SO3H
ONa
reaction
ОН О
H2SO4
NaOH
CO2, H20
OH Acetic anhydride
HO,
Benzene
Sodium
Salicylic acid
Aspirin
phenolate

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Step 1: benzene to benzene suphonic acid

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Step 2:: benzene symphonic acid to phenol

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Step 3: phenol to salicylic acid

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Step 4:: salicylic acid to aetyle salicylic acid

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