What is the product of the oxidation of 2-propanol with PCC?

Question

BlackTom AI · Accepted Answer

Secondary alcohols are oxidized to ketones: 2-propanol (isopropanol) is a secondary alcohol, so oxidation gives a ketone. Pyridinium chlorochromate (PCC) is a mild oxidizing agent (pyridinium chlorochromate) that oxidizes secondary alcohols to ketones (and primary alcohols to aldehydes under controlled conditions), but it does not cleave C–C bonds or overoxidize ketones to acids.

1. Relevant knowledge points and concepts
- Classification: 2-propanol is a secondary alcohol (structure CH3–CHOH–CH3).
- Oxidation outcome: Secondary alcohols → ketones (remove two H atoms to form C=O).
- Reagent behavior: PCC oxidizes alcohols to the next oxidation level without extensive further oxidation.

2. Step-by-step reasoning
- Start: 2-propanol: CH3–CHOH–CH3.
- Oxidation removes one hydrogen from the hydroxyl oxygen (–OH → =O) and one hydrogen from the α-carbon (the carbon bearing the OH). This converts the C–OH single bond into a C=O double bond.
- Product: CH3–CO–CH3 (a three-carbon ketone).

3. Structural/intermediate steps (showing atoms)
- 2-propanol formula: C3H8O (CH3–CHOH–CH3).
- After loss of 2 H (one from O–H and one from C–H): C3H6O (CH3–CO–CH3).
- Mechanistically PCC forms a chromate ester with the alcohol, then a β-hydrogen elimination yields the ketone plus reduced chromium species.

4. Why the correct answer is correct
- The product CH3–CO–CH3 is propanone (common name: acetone). This is exactly the expected ketone from oxidation of a secondary alcohol like 2-propanol with PCC.

5. Why other options are incorrect
- Propene: would require dehydration (elimination), not oxidation; PCC does not produce alkenes from alcohols under these conditions.
- Propanoic acid: would require full oxidation of a primary alcohol to a carboxylic acid; 2-propanol is secondary so it cannot give a carboxylic acid by simple oxidation.
- Propane: is a fully reduced hydrocarbon (no oxygen); reduction/hydrogenation, not oxidation, would give propane.
- Methyl ethanoate (an ester): would require esterification or C–C bond rearrangement, not the simple oxidation of a secondary alcohol.

6. Conclusion
Oxidation of 2-propanol (a secondary alcohol) with PCC yields the ketone propanone (CH3–CO–CH3). This matches the provided correct answer: propanone.

What is the product of the oxidation of 2-propanol with PCC?Single choice

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