Why is fluorene oxidized more readily than toluene, given that oxidation by O2 i

Question

Why is fluorene oxidized more readily than toluene, given that oxidation by O2 involves free-radical intermediates?

Please say why flourene is oxidized more readily.

Oxidizing the side chain of an arene usually requires a powerful oxidiz- ing agent such as potassium permanganate or chromium(III) oxide in acetic anhydride, as illustrated for the following reactions of toluene: COH KMnO CrO. Ac.O toluene The methylene side chain of fluorene, however,can be oxidized to a carbonyl group by a much milder oxidizing agent, air. NaOH fluorene 9-fluorenone This reaction, which yields the aromatic ketone 9-fluorenone, is ordinarily quite slow, but with vigorous stirring and a phase-transfer catals carried out in about an hour. can be

Explanation / Answer

Fluorene is oxidized more readily than toluene because when fluorene is oxidised to ketone, the aromaticity of the molecule increase since the aromaticity is shared throughout the entire molecule (two rings). We know that more the aromaticity more will be the stability of the mlecule. Therefore, there is an external deltaH of stabilization.

While in case of toluene, oxidation of toluene to benzoic acid or benzaldehyde does not increase aromaticity to any particular extent.

Hence, fluorene oxidized more readily than toluene.

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