Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: cairenrs on January 30, 2022, 07:41:18 PM
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I'm trying to understand this figure from a paper I'm reading, but I'm stuck on this part of their proposed reaction mechanism (see green box in attached image). As someone who barely passed organic chemistry 6 years ago, I have two questions.
1) How come the reaction starts at the meta hydroxyl group, but then switches to the hydroxl at the para position?
2) The paper states that the autooxidation reaction forms an o-semiquinone radical that quickly turns into o-quinone. But I thought the ortho-quinone would look like the image I have on the right - how come the authors consider their product as o-quinone when it clearly has an additional oxygen?
Any explanations or insight would be much appreciated!
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I only have time for a short reply right now, but one thing to keep in mind is that frequently only one of two or more resonance forms is drawn out; the rest are implicit.
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A) In order to form the semiquinone the meta and para position are both involved
B) Is is one of the resonance form of 0-quinone. if u google the resonance forms you will see what I am trying to say.