Provide a reasonable mechanism to account for the following reaction. NO2 H,SO4 HNO, Propose a mechanism to account for the formation of TNT from toluene. Why is the reaction below a very difficult reaction of accomplish? NO2 NO2 x.s. HNO, H2SO4 NO2

Provide a reasonable mechanism to account for the following reaction. NO2 H,SO4 HNO, Propose a mechanism to account for the formation of TNT from toluene. Why is the reaction below a very difficult reaction of accomplish? NO2 NO2 x.s. HNO, H2SO4 NO2

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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.27P

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Question

1
1 Provide a reasonable mechanism to account for the following reaction.
NO2
H,SO4
HNO;
Propose a mechanism to account for the formation of TNT from toluene. Why is the reaction below
a very difficult reaction of accomplish?
NO2
NO2
x.s. HNO,
H,SO,
NO2

Expert Solution

Step 1

When mixture of nitric acid and sulfuric acid reacts with benzene, nitration of benzene takes place and nitrobenzene is formed. In the first step, lone pair of electrons of oxygen atom of nitric acid takes up proton from sulfuric acid and an intermediate is formed in which oxygen atom and nitrogen atom attain positive charge.

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