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Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

3.3K
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.
3.3K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.9K
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...
2.1K
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...
11.8K
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

5.0K
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.
5.0K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.2K
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...
2.2K

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Related Experiment Video

Updated: Sep 26, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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Capturing Reactive Carbanions by Microdroplets.

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
Summary
This summary is machine-generated.

Aqueous microdroplets stabilize fleeting carbanion intermediates from organic reactions, enabling real-time detection via mass spectrometry. This breakthrough offers new insights into reaction mechanisms and carbanion stabilization.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Analytical Chemistry

Background:

  • Carbanions are transient intermediates in many organic and biological reactions.
  • Aqueous environments typically lead to rapid annihilation of carbanions, limiting their study.
  • Direct observation of carbanions is challenging due to their short lifetimes.

Purpose of the Study:

  • To investigate the potential of aqueous microdroplets to capture and stabilize reactive carbanion intermediates.
  • To enable real-time detection and mechanistic study of carbanions in classic organic reactions.
  • To explore the influence of solvent composition and charge density on carbanion capture efficiency.

Main Methods:

  • Utilized aqueous microdroplets to isolate and stabilize carbanion intermediates.
  • Employed desorption electrospray ionization mass spectrometry (DESI-MS) for detection.
  • Investigated four classic organic reactions: aldol and Knoevenagel condensations, alkyne alkylation, and Reimer-Tiemann reaction.
  • Varied solvent composition (e.g., water-methanol mixtures vs. pure water) and microdroplet charge density.

Main Results:

  • Successfully captured and stabilized carbanion intermediates from four distinct organic reactions.
  • Enabled real-time detection of these elusive species, providing new mechanistic insights.
  • Water-methanol microdroplets demonstrated superior performance in capturing carbanions compared to pure water.
  • Observed discriminatory behavior between carbanions and carbocations in microdroplets, contrasting previous findings.

Conclusions:

  • Aqueous microdroplets offer a novel platform for stabilizing and studying reactive carbanion intermediates.
  • This technique facilitates real-time mechanistic investigations of organic reactions.
  • Microdroplet solvent composition plays a critical role in the stabilization of charged intermediates, with water-methanol mixtures being effective for carbanions.