# Oxidation of acetophenone to benzoic acid

According to the solutions manual, the oxidation of acetophenone to benzoic acid can be achieved through addition of chromic acid and application of heat.

The solutions manual refers me to a section in the book which explains that when a benzylic hydrogen is present, a strong oxidizing agent combined with heat can perform oxidative cleavage.

Problem is that I don't see any benzylic hydrogens on acetophenone. Neither does its enol tautomer have any benzylic hydrogens ...

So, how is the oxidation of acetphenone to benzoic acid possible given what the book and solutions manual has told me? Self-consistency aside is this even a possible reaction?

• The mechanism of benzylic oxidation is not well understood. For acetophenone, consider what would happen if the enol tautomer were to undergo oxidative cleavage of its $\ce{C=C}$ bond, say using $\ce{KMnO4}$? – Ben Norris Feb 22 '15 at 2:12
• @BenNorris is that possible? It wasn't introduced in the text so I'm confused about a) why the text would introduce a reaction it doesn't even cover itself, unless I'm missing something and b) what exactly do we know strong oxidizers such as KMno4 and H2CrO4 to do? – Dissenter Feb 22 '15 at 2:21
• @ron what's the "Good Book"? – Dissenter Feb 22 '15 at 2:34
• What book is this? – jerepierre Feb 22 '15 at 18:58
• @jerepierre - Organic chemistry by Brown. – Dissenter Feb 22 '15 at 18:59