Which one of the following can be oxidised to the corresponding carbonyl compound?
A
2-hydroxy propane
B
Ortho-nitro phenol
C
propane
D
2-methyl-2-hydroxy propane
Step-by-Step Solution
Reaction Principle: The oxidation of alcohols involves the formation of a carbon-oxygen double bond with the cleavage of an O-H and a C-H bond.
Primary Alcohols (RCH2OH) are oxidised to Aldehydes (RCHO).
Secondary Alcohols (R2CHOH) are oxidised to Ketones (R2C=O).
Tertiary Alcohols (R3COH) do not undergo oxidation easily because they lack a hydrogen atom on the carbon bearing the hydroxyl group. Under strong conditions, they undergo cleavage to form mixtures of carboxylic acids containing fewer carbon atoms.
Analysis of Options:
2-hydroxy propane (Isopropyl alcohol): This is a secondary alcohol (CH3−CH(OH)−CH3). Upon oxidation (e.g., with CrO3), it yields Acetone (CH3−CO−CH3), which is a carbonyl compound.
Ortho-nitro phenol: Phenols are generally difficult to oxidise to simple carbonyl compounds; stronger oxidation yields quinones.
Propane: An alkane; controlled oxidation is required to form alcohols or aldehydes, but it is not the standard method for preparing carbonyls compared to alcohol oxidation.
2-methyl-2-hydroxy propane (tert-Butyl alcohol): This is a tertiary alcohol and does not oxidise to a corresponding carbonyl compound.
Conclusion: 2-hydroxy propane is the only compound listed that readily oxidises to a corresponding carbonyl compound (a ketone) without breaking the carbon chain.
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