Tertiary alcohols do not undergo oxidation reactions in the same way that primary and secondary alcohols do because of the structure of the alcohol and the mechanism of the oxidation process.
In a primary alcohol, the hydroxyl (-OH) group is attached to a carbon that is bonded to one other carbon (and two hydrogens), allowing oxidation to convert it first to an aldehyde and then to a carboxylic acid. In a secondary alcohol, the -OH group is attached to a carbon that is bonded to two other carbons (and one hydrogen), allowing it to be oxidized to a ketone.
Tertiary alcohols, on the other hand, have the hydroxyl group attached to a carbon that is bonded to three other carbons and no hydrogens. This structural configuration makes it impossible for the tertiary alcohol to be oxidized to a typical oxidation product (like an aldehyde, a ketone, or a carboxylic acid).
Instead, when subjected to strong oxidative conditions, tertiary alcohols are more likely to undergo cleavage or elimination reactions rather than traditional oxidation. Under severe conditions, they can sometimes react to form alkenes through dehydration or other degradation products, but they do not form oxidized products like primary and secondary alcohols do.
In summary, the inability of tertiary alcohols to be oxidized in a straightforward manner stems from their structure, which lacks the necessary hydrogen atoms that can be removed during the oxidation process.
2 answers