[Rutherford]

When an tertiary alcohol gets oxidized under extreme conditions, are all 3 C-C bonds cleveaged?
For example, if R₁R₂R₃C-OH gets oxidized are R₁COOH, R₂COOH, R₃COOH and HCOOH the products?

[discodermolide]

No I don't think so.
What conditions have you in mind?

[Schrödinger]

I think these are murky waters. When the oxidant is so powerful that it can break the adjacent bonds, I think one can expect a variety of products and not just one or two. Right?

[discodermolide]

I think you will get water and isobutene.

[Rutherford]

I think these are murky waters. When the oxidant is so powerful that it can break the adjacent bonds, I think one can expect a variety of products and not just one or two. Right?

That's why I wrote all the acids for example. Maybe some ketones would be produced and cleavaged, too.

I think you will get water and isobutene.

That would be reduction, I think.
All in all, I guess that a complex mixture will be made. Thanks.

[willug]

'Oxidation under extreme conditions?' Do you just mean burning it?? In that case CO2 and water if you do a good enough job :p

[souro10]

Well, it really depends on the method of oxidation i.e. how drastic the " extreme conditions " are.

For example, tertiary butyl alcohol in presence of copper catalyst at 300 degrees C produces isobutene.
But not all alcohols can tolerate this temperature. And a mixture of products are obtained.

Hence oxidation of tertiary alcohols do not have any synthetic utility; at least I cannot think of any.

[willug]

'That would be reduction, I think'

I don't think dehydration is either... Alkenes and alcohols are considered to be at the same 'oxidation level'.

[souro10]

Alkenes and alcohols are not at the same oxidation level.

Conversion of tertiary butyl alcohol to isobutene is technically called reduction.

I cited this example because if you pass ethanol vapours over heated Copper catalyst you get ethanal( by dehydrogenation) , but in case of a tertiary alcohol, you get alkene.

I think the question posted is way too general. It depends on the particular drastic method of oxidation used.

[willug]

This is the first result on google (for me anyway) for 'oxidation level';

http://classes.yale.edu/01-02/chem220a/studyaids/oxidationlevel/oxidationlevel.html

[sjb]

Alkenes and alcohols are not at the same oxidation level.

Conversion of tertiary butyl alcohol to isobutene is technically called reduction.

I cited this example because if you pass ethanol vapours over heated Copper catalyst you get ethanal( by dehydrogenation) , but in case of a tertiary alcohol, you get alkene.

I think the question posted is way too general. It depends on the particular drastic method of oxidation used.

That's possibly a change of mechanism. Are you agreed that hydration is not oxidation?

[souro10]

Alkenes and alcohols are not at the same oxidation level.

Conversion of tertiary butyl alcohol to isobutene is technically called reduction.

I cited this example because if you pass ethanol vapours over heated Copper catalyst you get ethanal( by dehydrogenation) , but in case of a tertiary alcohol, you get alkene.

I think the question posted is way too general. It depends on the particular drastic method of oxidation used.

That's possibly a change of mechanism. Are you agreed that hydration is not oxidation?

Yes, I was wrong. Thank you