Chapter 12.12, Problem 13P

Interpretation Introduction

Interpretation:

The compound ${\text{C}}_{\text{12}}{\text{H}}_{\text{14}}{\text{O}}_{\text{4}}$ obtained by chromic acid oxidation of $\text{4-tert-butyl-1,2-dimethylbenzene}$ is to be determined. The product expected from the chromic acid oxidation of $\text{2,3-dihydroindene}$ is to be determined.

Concept Introduction:

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Chromic acid is a strong oxidizing agent. It oxidizes alkyl benzene which has at least one benzylic hydrogen.

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Benzylic hydrogens are those attached to the benzylic carbon atoms.

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The benzene ring itself is not oxidized; only side chains are oxidized to produce benzoic acid.

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If a substituent attached to the benzene ring does not have any benzylic hydrogens, it remains as it is in the presence of chromic acid. It is not oxidized.