Alcoholic mix oxidation: strange product

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Andrea - 20 Feb 2004 21:34 GMT

Dear all,

I need a little help from organic chemists.
I have an alcoholic mix: ethanol (10%) + isopropanol (80%) + H20
(10%).
I add some NaOH and H2O2.
Because of H2O2 I can suppose that some kind of oxidation goes on.
Now, by analyzing the mix I find, and I'm sure, this molecule:

(CH3)2CH-O-CH2-O-CH(CH3)2

I tried some hypothesis, but I must realize that the usual pathways
for alcohols oxidation give other type of molecules.
Can someone help me, please?
Thank you in advance.

Andrea

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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
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Uncle Al - 24 Feb 2004 18:32 GMT

> Dear all,
>
[quoted text clipped - 11 lines]
> Can someone help me, please?
> Thank you in advance.

Why would anything happen at all? Do you have a proposed mechanism?
You propose a ridiculous product. How did you "analyze" it?

Isopropyl ethers are exceedingly hazardous because of air
hydroperoxidation. If you got acetone hydroperoxide trimer,

1) you will blow yourself up,
2) if you do not blow yourself up, Homeland Severity will shoot
you.

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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
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GeneralChemistryTutor - 24 Feb 2004 18:33 GMT

> Dear all,

> I need a little help from organic chemists.
> I have an alcoholic mix: ethanol (10%) + isopropanol (80%) + H20
> (10%).
> I add some NaOH and H2O2.
> Because of H2O2 I can suppose that some kind of oxidation goes on.
> Now, by analyzing the mix I find, and I'm sure, this molecule:

> (CH3)2CH-O-CH2-O-CH(CH3)2

> I tried some hypothesis, but I must realize that the usual pathways
> for alcohols oxidation give other type of molecules.
> Can someone help me, please?
> Thank you in advance.

> Andrea

I am not able to think of anything off the top. However, try looking
up the mechanism of hydroboration of akenenes and the subsequent
oxidation with hydrogen peroxide and NaOH in a standard organic
chemistry book. The oxidation characteristics are very similar to the
above molecule you had shown.

Other things to look into. Properties of diethyl ether...And that's
all I can think of right now.

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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

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Natural Science Forum / Chemistry / Organic Synthesis / February 2004

Alcoholic mix oxidation: strange product