[antimatter101]

MY organic chemistry book says that phenols can ge oxidized by strong oxidizing agents to these wierd molecules which look like diphenols, and then further oxidised to another molecule. What is that molecule and what is its properties?

[discodermolide]

If it's in your book you can either draw the structures and post them or post the names of these molecules.

[antimatter101]

How to draw them on the web?

[discodermolide]

You've got 63 posts on this forum, you should know how to do this by now.
Draw them scan them and upload them using the additional functions. I think the SMILES concept is not for you.

[antimatter101]

Okay, here is the screenshot.

I wonder why phenols can be oxidised so easily though they want to retain their aromaticity.

[antimatter101]

By the way, somehow "quinones" can be reduced to "hydroquinones", or something, using NaBH₄and then protonation by acid. The phenol was simply oxidised by any oxidising agent, such as KMnO₄, to yield the product.

The book was not asking a question; it was just showing a diagram of the reaction.

The question I should be asking is: Why are phenols oxidised so easily that that would mean destroying their aromaticity?

[discodermolide]

Have a look here under the section "oxidation of phenols" you may find something.
http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/alcohol2.htm

[antimatter101]

It says: error. The system cannot find the file specified.

Thanks though.

I will try researching on my own.

[discodermolide]

The aromatic ring is electron rich due to the oxygen atom making it (the ring) prone to oxidation.

[antimatter101]

Yes, but shouldn't the benzene ring try and retain aromaticity after it is oxidised?

[discodermolide]

No it remains as the quinone until it is reduced.

[antimatter101]

I wonder what the enthalpy change is for destroying aromaticity.
Also, I just realised that the quinone is conjugated.
Does that mean that very nucleophilic aromatic compounds are willingly oxidised to their conjugate forms?

[antimatter101]

The conjugate form will stabilise the molecule a bit, though.

[discodermolide]

What do you mean with nucleophillic aromatic compounds?
I have no idea what the enthalpy change is, it will be documented somewhere but where?

[antimatter101]

Nucleophilic means "got more electrons".

Aromatic compounds are usually made more nucleophilic by ortho and para deriving activators.