I recently came across a question where naphthalene undergoes oxidation with sodium dichromate in presence of sulfuric acid. The given options were benzoic acid, phthalic acid, decalin, and tetralin.

Reaction of naphthalene with sodium dichromate/sulfuric acid

I assumed the reaction to be similar to that of the reaction between potassium permanganate under acidic conditions, yielding phthalic acid. This reaction was described in Oxidation of naphthalene with KMnO4.

Could anyone please clarify the reaction, whether my assumption is correct, and explain the mechanism?


It depends on the reaction conditions.

I suspect the answer the question setter wants to see is phthalic acid, but the true answer is none of these. I have found multiple references (such as this US Patent and this Org. Syn prep) that refer to the production of naphthoquinones by oxidation of naphthalenes with high valent Chromium reagents under acid conditions.


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