교과서 질문
What alkyl bromide(s) should be used in the malonic ester synthesis of each of the following carboxylic acids?
a. propanoic acid
b. 2-methylpropanoic acid
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24. Enolate Chemistry: Reactions at the Alpha-Carbon
Malonic Ester Synthesis
객관식
Which of the following statements best describes the main purpose of the malonic ester synthesis in organic chemistry?
A
It is used to prepare substituted derivatives by alkylation and subsequent decarboxylation.
B
It is a technique for reducing carboxylic acids to primary alcohols using .
C
It is a method for converting alcohols into aldehydes using as an oxidizing agent.
D
It is a process for synthesizing alkenes from alkyl halides via elimination reactions.
검증된 단계별 안내1
Understand that the malonic ester synthesis is a classical method in organic chemistry used to prepare substituted acetic acid derivatives.
Recognize that the process involves the alkylation of a malonic ester, which contains two ester groups adjacent to a methylene group, making the methylene hydrogens acidic and able to be deprotonated by a strong base.
After deprotonation, the resulting carbanion can undergo alkylation with an alkyl halide, introducing a substituent at the methylene position.
Following alkylation, the compound is subjected to hydrolysis and then decarboxylation, which removes one carboxyl group as carbon dioxide, yielding a substituted acetic acid.
Note that this method is distinct from reductions with LiAlH4, oxidations with PCC, or elimination reactions to form alkenes, which are different types of organic transformations.
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