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Related Concept Videos

Carbocations02:10

Carbocations

13.3K
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...
13.3K
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

5.2K
α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
5.2K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.6K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.6K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.0K
Nucleophilic Addition to the Carbonyl Group: General Mechanism01:18

Nucleophilic Addition to the Carbonyl Group: General Mechanism

7.6K
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...
7.6K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

8.5K
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
8.5K

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Related Experiment Video

Updated: Jan 5, 2026

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

Published on: April 19, 2019

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A Carbene-Extended ATRA Reaction.

Guojiao Wu1, Jennifer Börger1, Axel Jacobi von Wangelin1

  • 1Department of Chemistry, University of Hamburg, Martin Luther King Pl 6, 20146, Hamburg, Germany.

Angewandte Chemie (International Ed. in English)
|October 16, 2019
PubMed
Summary

This study expands atom-transfer radical addition (ATRA) reactions beyond typical 1,2-bifunctional products. It introduces a novel method for synthesizing 1,3-bifunctional adducts using carbenoids and alkynes under mild conditions.

Keywords:
alkynesatom-transfer radical additioncarbenescobaltdiazo compounds

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Atom-transfer radical addition (ATRA) reactions are valued for their simplicity, versatility, and atom economy in organic synthesis.
  • Existing ATRA methods primarily yield 1,2-bifunctional products via addition across C=C double bonds.

Purpose of the Study:

  • To expand the scope of ATRA reactions by developing a method for synthesizing 1,3-bifunctional adducts.
  • To introduce a novel synthetic strategy combining 1,1-ATRA to carbenoids and 1,2-ATRA to alkynes.

Main Methods:

  • Utilizing a combination of 1,1-ATRA to a carbenoid and 1,2-ATRA to an alkyne.
  • Employing mild reaction conditions (room temperature, 5 hours).
  • Using a single, commercially available catalyst (CoBr2, dppbz).

Main Results:

  • Successful synthesis of 1,3-bifunctional adducts, expanding the utility of ATRA reactions.
  • Demonstration of the reaction's efficiency under mild, user-friendly conditions.
  • The same catalyst facilitates both the carbenoid and alkyne addition steps.

Conclusions:

  • This work significantly broadens the synthetic applications of ATRA by enabling the formation of 1,3-bifunctional compounds.
  • The developed method offers a versatile and efficient route to complex organic molecules.
  • The use of a single catalyst under mild conditions enhances the practicality of this new synthetic approach.