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Topic: Oxidation of fluorene vs oxidation of toluene  (Read 4997 times)

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Offline okemstudent11

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Oxidation of fluorene vs oxidation of toluene
« on: April 11, 2011, 07:34:46 PM »
Explain why fluorene is oxidized by O2 much more rapidly than is toluene, given that oxidation by O2 involves free-radical intermediates.
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Offline okemstudent11

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Re: Oxidation of fluorene vs oxidation of toluene
« Reply #1 on: April 12, 2011, 03:40:34 AM »
I don't understand. Is it because the free-radical intermediates in the mechanism of fluorene are more unstable---> therefore, there is a faster rate of reaction than in the mechanism for toluene?
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Offline orgopete

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Re: Oxidation of fluorene vs oxidation of toluene
« Reply #2 on: April 22, 2011, 06:18:40 PM »
Let's spin it around. Why are radical bromination reactions more selective than chlorination reactions? Why might fluorene react more rapidly? If the rate of reaction is faster for fluorene and it is a radical reaction, what does that tell you about the rate determining step?
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Offline Kadabrium

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Re: Oxidation of fluorene vs oxidation of toluene
« Reply #3 on: April 23, 2011, 06:56:10 AM »
fluorene radical is conjungated to two aromatic rings
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