Which one of the following can be oxidised to the corresponding carbonyl compound :-
A
o-Nitrophenol
B
Phenol
C
2-methyl-2-hydroxy propane
D
2-hydroxy propane
The answer is D.
Solution
An alcohol can be oxidised to a carbonyl compound only if the carbon bearing the –OH group has at least one hydrogen atom. 2-hydroxy propane is propan-2-ol, $CH_3CH(OH)CH_3$, a secondary alcohol. Its carbinol carbon has one H, so it is oxidised to the ketone acetone: $CH_3CH(OH)CH_3 \xrightarrow{[O]} CH_3COCH_3 + H_2O$ 2-methyl-2-hydroxy propane is tert-butyl alcohol, $(CH_3)_3C-OH$. It has no H on the carbinol carbon, so it is not oxidised to a carbonyl compound (under strong conditions it breaks down instead). In phenol and o-nitrophenol, the –OH is attached to an aromatic ring carbon that has no H; they cannot form a corresponding carbonyl compound. So 2-hydroxy propane can be oxidised to the corresponding carbonyl compound (acetone).
ConceptSecondary alcohol oxidised to ketone
Oxidation of Alcohols in past papers
2 questions from this chapter have appeared across 2 exam years.