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Related Concept Videos

Carbocations02:10

Carbocations

12.8K
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...
12.8K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

9.1K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
9.1K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.4K
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...
4.4K
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

3.7K
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
3.7K
Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

3.0K
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
3.0K
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

7.0K
The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π...
7.0K

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Updated: Nov 18, 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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Aqueous Microdroplets Capture Elusive Carbocations.

Anubhav Kumar1, Supratim Mondal1, Shibdas Banerjee1

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

Journal of the American Chemical Society
|February 3, 2021
PubMed
Summary
This summary is machine-generated.

Researchers captured short-lived carbocations using water microdroplets. This new method allows for mass spectrometric detection of these transient species, advancing organic reaction studies.

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Area of Science:

  • Organic Chemistry
  • Analytical Chemistry
  • Physical Chemistry

Background:

  • Carbocations are highly reactive, transient intermediates crucial in organic and biological reactions.
  • Observing and characterizing carbocations has been historically challenging due to their short lifetimes.
  • Olah's superacidic solution method enabled the first successful capture and NMR characterization of transient carbocations.

Purpose of the Study:

  • To develop a novel method for capturing and detecting short-lived carbocations.
  • To utilize water microdroplets for the direct capture of carbocations from reaction mixtures.
  • To enable gas-phase mass spectrometric analysis of these fleeting intermediates.

Main Methods:

  • Employing desorption electrospray ionization mass spectrometry (DESI-MS).
  • Utilizing water microdroplets to capture carbocations directly from reaction aliquots.
  • Analyzing various short-lived carbocations generated from elimination, substitution, and oxidation reactions.

Main Results:

  • Demonstrated successful capture and gas-phase detection of transient carbocations using water microdroplets.
  • Showcased the effectiveness of aqueous microdroplets over organic microdroplets for carbocation capture.
  • Characterized carbocations with average lifetimes ranging from nanoseconds to picoseconds.

Conclusions:

  • Water microdroplets provide an effective medium for capturing and stabilizing reactive carbocations.
  • DESI-MS with aqueous microdroplets offers a viable technique for studying transient carbocations.
  • This method enhances the understanding of reaction mechanisms involving carbocation intermediates.