Tertiary alcohols cannot be oxidized due to the absence of hydrogen atoms on the carbon atom bonded to the hydroxyl (-OH) group. The oxidation process requires breaking a carbon-carbon (C-C) bond, which is necessary for the formation of carbonyl compounds. When attempting to oxidize tertiary alcohols, the energy required to remove hydrogen from non-adjacent carbon atoms complicates the process. The only effective method for oxidizing tertiary alcohols involves the use of fluorine gas, which can break the entire molecule and facilitate oxidation.
PREREQUISITESChemistry students, organic chemists, and researchers interested in alcohol oxidation and reaction mechanisms will benefit from this discussion.
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).