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Videos de Conceptos Relacionados

Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

4.3K
The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.8K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
7.8K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

16.0K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.0K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.4K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Síntesis mediada por la luz de anhídridos alifáticos por carbonilación catalizada por Cu de haluros de alquilo

Pinku Tung1, Neal P Mankad1

  • 1Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607, United States.

Journal of the American Chemical Society
|April 19, 2023
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un nuevo método de un solo paso para la producción de anhídridos ácidos utilizando la catálisis del cobre y la luz, evitando los metales preciosos. Este proceso sostenible ofrece una alternativa eficiente para la síntesis química industrial.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • La fotoquímica

Sus antecedentes:

  • Los anhídridos ácidos son productos químicos industriales cruciales utilizados en la síntesis de polímeros, productos farmacéuticos y otros productos básicos.
  • Los métodos de producción actuales a menudo implican síntesis en varios pasos y catalizadores de metales preciosos, como el rodio para el anhídrido acético.
  • Se necesitan métodos más eficientes y sostenibles para la producción de anhídridos ácidos.

Objetivo del estudio:

  • Desarrollar una síntesis directa de un solo paso para anidridos ácidos alifáticos simétricos.
  • Establecer un proceso de carbonilación catalizado por el cobre mediado por la luz que evite los metales preciosos.
  • Demostrar un método sostenible y escalable para la producción industrial de anhídrido.

Principales métodos:

  • Una nueva carbonilación de alquilo (pseudo) haluros mediada por la luz y catalizada por el cobre.
  • Generación in situ de un fotocatalizador Cu0 heterogéneo utilizando sales y bases simples de cobre.
  • Investigación del mecanismo radical subyacente a la transformación.

Principales resultados:

  • Síntesis directa exitosa de anidridos ácidos alifáticos simétricos en un solo paso.
  • Se mantiene una alta eficiencia y selectividad a escala.
  • El proceso opera a través de un mecanismo radical, que ofrece varias características beneficiosas para la síntesis química.

Conclusiones:

  • El proceso catalizado por Cu desarrollado proporciona una alternativa eficiente y sostenible para la producción de anhídridos ácidos básicos.
  • Este método elimina la necesidad de catalizadores de metales preciosos y procedimientos en varios pasos.
  • Los hallazgos permiten la ingeniería de procesos a granel para la fabricación de anhídrido rentable y respetuosa con el medio ambiente.