The discussion centers on the oxidation of tertiary alcohols, specifically addressing why they cannot be oxidized and the implications of breaking carbon-carbon (C-C) bonds in the process. Participants explore theoretical aspects of organic chemistry related to oxidation reactions and molecular structure.
Participants express differing views on the oxidation of tertiary alcohols, with some agreeing on the inability to oxidize them under normal conditions, while others propose alternative methods. The discussion remains unresolved regarding the feasibility of oxidation pathways and the implications of breaking C-C bonds.
Participants highlight limitations related to the structural constraints of tertiary alcohols and the energy requirements for potential oxidation reactions. There are unresolved questions about the mechanisms involved in breaking C-C bonds during oxidation.
GeneralOJB said:I've learned that tertiary alcohols can't be oxidised because the carbon bearing the OH contains no hydrogen atoms. But why can't the oxygen just take the hydrogen from the OH and another hydrogen from another carbon atom on the molecule?
I also read that it would involve breaking a C-C bond - how so?
ldc3 said:If you took the hydrogen from the oxygen and another hydrogen from a non-adjacent carbon atom, you would then need to connect the oxygen to something and the carbon to something. Also, taking a hydrogen from non-adjacent carbon takes more energy since the oxygen (without a hydrogen) transfers some of it charge to the adjacent carbon, which makes the adjacent hydrogen easier to remove.
Since there are only C-C bonds on a tertiary alcohol (aside from the OH), if the OH is converted to a double bond to the carbon, then a C-C bond would need to be broken (since carbon cannot have 5 bonds).