2004 AIPMT Alcohols, Phenols and EthersOxidation of Alcohols Easy Question 1 of 2 in Oxidation of Alcohols

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).

Concept Secondary alcohol oxidised to ketone

Oxidation of Alcohols in past papers

2 questions from this chapter have appeared across 2 exam years.