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Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
2.9K
Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

2.1K
The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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Carbocations02:10

Carbocations

11.8K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

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Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Video Experimental Relacionado

Updated: Sep 26, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Captura de carbaniones reactivos mediante microgotas

Anubhav Kumar1, Supratim Mondal1, Mohammad Mofidfar2

  • 1Department of Chemistry, Indian Institute of Science Education and Research Tirupati, Tirupati 517507, India.

Journal of the American Chemical Society
|April 22, 2022
PubMed
Resumen
Este resumen es generado por máquina.

Las microgotas acuosas estabilizan los intermedios de carbanión fugaces de las reacciones orgánicas, lo que permite la detección en tiempo real a través de la espectrometría de masas. Este avance ofrece nuevos conocimientos sobre los mecanismos de reacción y la estabilización del carbanión.

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Área de la Ciencia:

  • Química orgánica
  • Química Física
  • Química analítica

Sus antecedentes:

  • Los carbaniones son intermedios transitorios en muchas reacciones orgánicas y biológicas.
  • Los entornos acuosos generalmente conducen a la rápida aniquilación de los carbaniones, lo que limita su estudio.
  • La observación directa de los carbaniones es difícil debido a su corta vida útil.

Objetivo del estudio:

  • Investigar el potencial de las microgotas acuosas para capturar y estabilizar los intermedios reactivos de carbanión.
  • Permitir la detección en tiempo real y el estudio mecanicista de los carbaniones en reacciones orgánicas clásicas.
  • Explorar la influencia de la composición del disolvente y la densidad de carga en la eficiencia de captura del carbanión.

Principales métodos:

  • Se utilizan microgotas acuosas para aislar y estabilizar los intermedios de carbanión.
  • Se utiliza la espectrometría de masas de ionización por electrospray de desorción (DESI-MS) para la detección.
  • Investigó cuatro reacciones orgánicas clásicas: las condensaciones de aldol y Knoevenagel, la alquilación de alquinos y la reacción de Reimer-Tiemann.
  • Composición variada de disolventes (por ejemplo, mezclas de agua y metanol frente a agua pura) y densidad de carga de microgotas.

Principales resultados:

  • Se capturaron y estabilizaron con éxito los intermedios de carbanión de cuatro reacciones orgánicas distintas.
  • Permitió la detección en tiempo real de estas especies escurridizas, proporcionando nuevos conocimientos mecanicistas.
  • Las microgotas de agua-metanol demostraron un rendimiento superior en la captura de carbaniones en comparación con el agua pura.
  • Comportamiento discriminatorio observado entre carbaniones y carbocationes en microgotas, en contraste con hallazgos anteriores.

Conclusiones:

  • Las microgotas acuosas ofrecen una nueva plataforma para estabilizar y estudiar los intermedios reactivos de carbanión.
  • Esta técnica facilita las investigaciones mecanicistas en tiempo real de las reacciones orgánicas.
  • La composición del disolvente de microgotas juega un papel crítico en la estabilización de los intermedios cargados, siendo efectivas las mezclas de agua y metanol para los carbaniones.