Answer

Answer

Oxidation of 3-(Hydroxymethyl)cyclopentanol

Reaction Overview

The starting compound, 3-(hydroxymethyl)cyclopentanol, contains both a primary alcohol (–CH₂OH) and a secondary alcohol attached to a cyclopentane ring.

Reagents and Conditions

• Oxidizing Agent: Sodium hypochlorite (NaOCl)
• Acid: Acetic acid (AcOH)
• Temperature: 0°C (cold conditions)

Chemical Principle

NaOCl in AcOH at 0°C acts as a mild oxidizing agent. Under these conditions:

• Primary alcohols are oxidized to aldehydes
• Secondary alcohols remain largely unreacted

Mechanism Summary

1. Protonation of the alcohol by AcOH
2. Formation of hypochlorous acid (HOCl)
3. Oxidation of the –CH₂OH group to an aldehyde –CHO
4. Secondary hydroxyl group remains unchanged

Major Product

This product retains the hydroxyl group on the ring and replaces the hydroxymethyl side chain with an aldehyde group.

Conclusion

The selective oxidation of 3-(hydroxymethyl)cyclopentanol using NaOCl and AcOH at low temperature leads to 3-hydroxycyclopentane carbaldehyde. This transformation is highly useful in synthesis when controlled oxidation is desired.