Textbook Question
What reagents should be used to prepare the following compounds?
c.
24. Enolate Chemistry: Reactions at the Alpha-Carbon
Enamine Alkylation and Acylation
Multiple Choice
Which of the following can NOT be formed through the stork enamine reaction with 2-butanone?
A
3-pentanone
B
3-methyl-2-butanone
C
2-octanone
D
3-octanone
Verified step by step guidance1
Understand the Stork enamine reaction: It involves the formation of an enamine from a ketone and a secondary amine, followed by an alkylation or acylation step.
Identify the starting material: In this case, the ketone is 2-butanone, which will form an enamine with a secondary amine.
Consider the possible alkylation or acylation reactions: The enamine can react with an alkyl halide or an acyl chloride to form a new carbon-carbon bond.
Analyze the products: 3-pentanone and 3-methyl-2-butanone can be formed by alkylation of the enamine with appropriate alkyl halides. However, forming 2-octanone would require a different starting ketone or a more complex reaction pathway.
Conclude which product cannot be formed: Since 2-octanone cannot be formed directly from 2-butanone through a simple Stork enamine reaction, it is the correct answer.
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