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Considering oxidation mechanism of side-chains in arenes, it is known that side-chains get oxidized to carboxylic group ($-COOH$).

Below is a picture of 2-Methyl, 2-Phenyl Propane. When it gets refluxed with acidified $KMnO_4$ or acidified $K_2Cr_2O_7$, it should be oxidized to give benzoic acid.

But according to the provided source, it seems 2-Methyl, 2-Phenyl Propane doesn't react with the above oxidizing agents.

My question is,

Why does this compound disobey the general oxidation of benzyl derivatives?

Note, the source has a OH on position 4 of the ring, that makes it difficult for me to name it.

Source: https://papers.gceguide.com/A%20Levels/Chemistry%20(9701)/9701_s13_qp_41.pdf Qno:5 c) i)

Or is the OH that makes the difference in this question?

2-Methyl,2-Phenyl Propane:

enter image description here

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    $\begingroup$ For oxidation of aromatic side chains, you must have at least one Benzylic hydrogen. tert-butyl Benzene (which is actually 2-methyl,2-phenyl propane) doesn't have any benzylic hydrogen.. $\endgroup$
    – Soumik Das
    Apr 24, 2019 at 6:01
  • $\begingroup$ @SoumikDas Oh, hadn't considered that? Should I remove this thread? $\endgroup$
    – Amar30657
    Apr 24, 2019 at 6:09
  • $\begingroup$ @Amar30657 No. I rather suggest either comment or answer your own question to let others with the doubt have it answered on ChemSE; you may close the question later on. (The question has been answered by Soumik, tho) $\endgroup$
    – Kartik
    Apr 24, 2019 at 9:41

1 Answer 1

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For oxidation of aromatic side chains, you must have at least one Benzylic hydrogen. tert-butyl Benzene (which is actually 2-methyl,2-phenyl propane) doesn't have any benzylic hydrogen.

-By @Soumik Das

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