Q.What is the action of hydrazine on cyclopentanone in presence of KOH in ethylene glycol?
Step 1. Recognise the reagent combination (section 12.8.3b). Hydrazine (H2N-NH2) followed by heating with KOH in a high-boiling solvent such as ethylene glycol is specifically the Wolf-Kishner reduction.
Step 2. Stage 1: hydrazone formation. Cyclopentanone (a five-membered ring ketone) reacts with hydrazine, losing water, to form the corresponding cyclopentanone hydrazone (its ring >C=O replaced by >C=N-NH2).
Step 3. Stage 2: base-mediated reduction. Heating this hydrazone with KOH in ethylene glycol drives off nitrogen gas (N2) and converts the >C=N-NH2 all the way to a plain ring -CH2-, i.e. the ketone's oxygen is fully replaced by two hydrogens.
Step 4. Identify the product. Since cyclopentanone's ring carbon bearing the carbonyl becomes a plain -CH2- ring carbon, the overall five-membered ring becomes fully saturated cyclopentane.
Wolf-Kishner reduction converts cyclopentanone's >C=O to -CH2-, giving cyclopentane (via the cyclopentanone hydrazone intermediate, with loss of N2).
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