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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: okemstudent11 on April 11, 2011, 07:34:46 PM

Title: Oxidation of fluorene vs oxidation of toluene
Post by: okemstudent11 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.

Title: Re: Oxidation of fluorene vs oxidation of toluene
Post by: okemstudent11 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?

Title: Re: Oxidation of fluorene vs oxidation of toluene
Post by: orgopete 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?

Title: Re: Oxidation of fluorene vs oxidation of toluene
Post by: Kadabrium on April 23, 2011, 06:56:10 AM

fluorene radical is conjungated to two aromatic rings