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How many of the following reagents can bring about the transformation: propan-2-ol -> propan-2-one (acetone)? Reagents: (i) Cu, 300 deg C (ii) O3 / Zn, H2O (iii) NBS (iv) Zn-Hg / HCl

1. Cu, 300°C
2. O3 / Zn, H2O
3. NBS
4. Zn-Hg / HCl

Correct answer: Cu, 300°C

Solution

Passing propan-2-ol vapour over hot copper at ~300 deg C causes catalytic dehydrogenation: CH3CH(OH)CH3 -> CH3COCH3 + H2. Ozonolysis requires a C=C double bond; NBS brominates allylic/benzylic C-H; Zn-Hg/HCl (Clemmensen) reduces C=O to CH2, not the reverse.

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