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Malonic Ester Synthesis
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Malonic Ester Synthesis
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24. Enolate Chemistry: Reactions at the Alpha-Carbon / Malonic Ester Synthesis / Problem 1
Problem 1
Explain why the malonic ester synthesis can not be used to produce the following carboxylic acid.
A
The reaction occurs with straight-chain alkyl halides only. Since the alkyl halide required to produce the given carboxylic acid has a cyclic structure, it can not be used to produce the given carboxylic acid.
B
The reaction involves the S
N
2 attack of an enolate to the alkyl halide. Since the alkyl halide required to produce the given carboxylic acid is very hindered, it can not undergo an S
N
2 reaction.
C
The reaction can produce aromatic carboxylic acids only. Since the given carboxylic acid is not aromatic, it can not be prepared using this reaction.
D
None of these.
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