유기화학실험 aldol condensation

본 내용은 " 유기화학실험 aldol condensation " 의 원문 자료에서 일부 인용된 것입니다. 2023.07.18

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• 1. aldol condensation

  aldol condensation(addition+dehydration)은 반응물인 benzaldehyde(2eq)와 acetone(1eq)이 NaOH(base), H2O/EtOH mixture 용매 하에서 반응하여 trans, trans-isomer인 dibenzylideneacetone(dibenzalacetone)을 생성하는 반응이다. 이 반응은 모든 단계가 평형 반응이어서 역반응도 가능하므로 100%의 수율을 얻을 수는 없다. 반응 메커니즘을 보면 acetone의 α-carbon의 C-H 결합이 산성이어서 OH-에 의해 deprotonation되어 enolate ion이 생성되고, 이 enolate ion이 benzaldehyde의 carbonyl carbon과 반응하여 β-hydroxy carbonyl compound가 생성된다. 이후 빠른 dehydration 반응을 거쳐 최종적으로 trans, trans-isomer인 dibenzylideneacetone이 생성된다.

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• 1. aldol condensation

  Aldol condensation is an important organic reaction in which an enolate ion or enol reacts with a carbonyl compound to form a β-hydroxy carbonyl compound, also known as an aldol. This reaction is widely used in the synthesis of various organic compounds, particularly in the pharmaceutical and fine chemical industries. The reaction involves the formation of a new carbon-carbon bond, making it a valuable tool for building complex molecular structures. The mechanism of aldol condensation involves several steps, including enolization, nucleophilic addition, and dehydration, which can be influenced by various factors such as the nature of the reactants, the presence of catalysts, and the reaction conditions. Understanding and optimizing the aldol condensation reaction is crucial for the efficient synthesis of a wide range of organic compounds with diverse applications.