Reactivity and orientation of Electrophilic substitution 19-38. - Organic Chemistry (Mcmurry)

Question

Question: Predict the products of the wolff-Kishner reduction reactions below. Provide the electron pushing mechanism for each, beginning from the hydrazone intermediate.

Step-by-Step Solution

Answer

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Step1: Wolff-Kishner reduction

Aldehydes and ketones can be converted into a hydrazine derivative by reaction with hydrazine. These hydrazones can be further converted to the parent alkane by action of base and heat. Both these reactions together are called Wolf-Kishner reduction

Step 2: Mechanism (a)

Step 3: Mechanism (b)

Step 4: Mechanism (c)

Step 5: Mechanism (d)

Step 6: Explanation for common feature

All these reactions follow the same mechanistic pathway.