Chapter 18, Problem 18.18P

Interpretation Introduction

(a)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The carbonyl group of an aldehyde or a ketone is reduced to a $-{\text{CH}}_{\text{2}}-$ group when treated with hydrazine under mildly acidic conditions, followed by heating with a strong base like NaOH. The reaction is known as Wolff-Kishner reduction. Initially, hydrazine adds to the carbonyl carbon ro produce a hydrazone. The mechanism of formation of hydrazone is similar to the formation of an imine. Thereafter, a series of proton transfer steps leads to the original carbonyl carbon being reduced to $-{\text{CH}}_{\text{2}}-$ with the loss of highly stable nitrogen molecule.

Interpretation Introduction

(b)

Interpretation:

The complete, detailed mechanism of the given reaction is to be drawn, and the major product is to be predicted.

Concept introduction:

The carbonyl group of an aldehyde or a ketone is reduced to a $-{\text{CH}}_{\text{2}}-$ group when treated with hydrazine under mildly acidic conditions, followed by heating with a strong base like NaOH. The reaction is known as Wolff-Kishner reduction. Initially, hydrazine adds to the carbonyl carbon ro produce a hydrazone. The mechanism of formation of hydrazone is similar to the formation of an imine. Thereafter, a series of proton transfer steps leads to the original carbonyl carbon being reduced to $-{\text{CH}}_{\text{2}}-$ with the loss of highly stable nitrogen molecule.