a) Interpretation: The aromatic substance obtained as the product, when m-nitroisopropyl benzene is oxidized with KMnO 4 , is to be given. Concept introduction: The benzene ring is inert to even strong oxidizing agents like KMnO 4 and Na 2 Cr 2 O 7 . However the alkyl side chains with benzylic hydrogen atoms are readily oxidized by these reagents into carboxyl groups. Compounds having no benzylic hydrogen atoms in the side chain are not oxidized. To give: The aromatic substance obtained as the product, when m-nitroisopropyl benzene is oxidized with KMnO 4 .

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Question

Chapter 16.8, Problem 18P

Interpretation Introduction

a)

Interpretation:

The aromatic substance obtained as the product, when m-nitroisopropyl benzene is oxidized with KMnO₄, is to be given.

Concept introduction:

The benzene ring is inert to even strong oxidizing agents like KMnO₄ and Na₂Cr₂O₇. However the alkyl side chains with benzylic hydrogen atoms are readily oxidized by these reagents into carboxyl groups. Compounds having no benzylic hydrogen atoms in the side chain are not oxidized.

To give:

The aromatic substance obtained as the product, when m-nitroisopropyl benzene is oxidized with KMnO₄.

Interpretation Introduction

b)

Interpretation:

The aromatic substance obtained as the product, when p-tert-butyltoluene is oxidized with KMnO₄, is to be given.

Concept introduction:

The benzene ring is inert to even strong oxidizing agents like KMnO₄ and Na₂Cr₂O₇. However the alkyl side chains with benzylic hydrogen atoms are readily oxidized by these reagents into carboxyl groups. Compounds having no benzylic hydrogen atoms in the side chain are not oxidized.

To explain:

The aromatic substance obtained as the product when p-tert-butyl toluene is oxidized with KMnO₄.

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