Oxidizing the side chain of an arene usually requires a powerful oxidizing agent
ID: 906067 • Letter: O
Question
Oxidizing the side chain of an arene usually requires a powerful oxidizing agent such as potassium permanganate or chromium(1ll) oxide in acetic anhydride, as illustrated for the following reactions of toluene: The methylene side chain of fluorene, however, can be oxidized to a carbonyl group by a much milder oxidizing agent, air. This reaction, which yields the aromatic ketone 9-fluorenone. is ordinarily quite slow, but with vigorous stirring and a phase-transfer catalyst, it can he carried out in about an hour.Explanation / Answer
Free radical intermediate will be formed on that C which will have O.
In 1st, this free radical intermediate is stabilised by resonance through only 1 ring. Also it was destrying the aromaticity of the ring
In 2nd, the free radical is stabilised by resonance by 2 ring
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