Asked by Ashlee Watson on Sep 27, 2024
Verified
What intermediate occurs when a ketone undergoes a Wolff-Kishner reduction?
A) a cyanohydrin
B) a hydrated aldehyde
C) a carboxylate
D) a semicarbazone
E) a hydrazone
Wolff-Kishner Reduction
A chemical reaction used to convert carbonyl groups (C=O) into methylene (CH2) groups by treatment with hydrazine (N2H4) and a strong base.
Ketone
An organic compound characterized by a carbonyl group (C=O) bonded to two carbon atoms, common in sugars and fragrances.
Hydrazone
A compound formed by the reaction of a hydrazine with a ketone or aldehyde, characterized by a –NHN=C– linkage.
- Understand the use and mechanism of Wolff-Kishner reduction in organic chemistry.
Verified Answer
CD
Charles Dandanabout 9 hours ago
Final Answer :
E
Explanation :
During the Wolff-Kishner reduction, a hydrazone intermediate is formed by the reaction of the ketone with hydrazine. This hydrazone intermediate is then treated with strong base and high heat to undergo a rearrangement and eliminate nitrogen gas, resulting in the formation of the corresponding alkane.
Learning Objectives
- Understand the use and mechanism of Wolff-Kishner reduction in organic chemistry.