Carboxylic acid from Alkylbenzenes

Concept: Oxidative cleavage of the side chain on an aromatic ring, degrading the entire alkyl chain down to a single terminal carboxyl carbon attached directly to the ring. The reaction absolutely requires the starting group to possess at least one benzylic hydrogen atom.

Notation:

• $$\text{Toluene / Ethylbenzene}$$ = Viable reactants containing active benzylic protons; Bulky groups lacking benzylic hydrogens (like tert-butylbenzene) will completely fail to react.