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Which of the following can be oxidized to the corresponding carbonyl compound?

1. 2-hydroxypropane
2. o-nitrophenol
3. phenol
4. 2-methyl-2-hydroxypropane

Correct answer: 2-hydroxypropane

Solution

Only 2-hydroxypropane (isopropyl alcohol, a secondary alcohol) is oxidised to a carbonyl compound (acetone). tert-Butanol has no alpha-H and cannot give a carbonyl, and phenols/nitrophenols are not oxidised to simple carbonyls.

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