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Related Concept Videos

Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

10.7K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
10.7K
Electrophiles02:28

Electrophiles

12.1K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
12.1K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

9.8K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
9.8K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.9K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.9K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.1K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
3.1K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

9.2K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
9.2K

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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
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Electrohalogenation of organic compounds.

Marcos R Scheide1, Celso R Nicoleti1, Guilherme M Martins1

  • 1Departamento de Química, Universidade Federal de Santa Catarina - UFSC, Florianópolis, 88040-900 SC, Brazil. braga.antonio@ufsc.br martins.chem@gmail.com.

Organic & Biomolecular Chemistry
|March 3, 2021
PubMed
Summary

This review covers recent advances in electrochemical halogenation, a green chemistry approach for synthesizing essential halogen-containing organic compounds. Electrosynthesis offers an environmentally friendly method for fluorination, chlorination, bromination, and iodination reactions.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Electrosynthesis

Background:

  • Halogen-containing compounds are crucial intermediates in academic research and pharmaceutical industries.
  • Traditional halogenation methods can pose environmental challenges.
  • Electrosynthesis offers a sustainable alternative, aligning with green chemistry principles.

Purpose of the Study:

  • To provide a comprehensive overview of recent advancements in electrochemical halogenation of organic compounds.
  • To highlight the utility of electrosynthesis as an environmentally friendly methodology.
  • To discuss various halogenation reactions including fluorination, chlorination, bromination, and iodination.

Main Methods:

  • Electrochemical synthesis using electrolysis as a redox medium.
  • Review of reactions targeting sp, sp2, and sp3 carbon centers.
  • Analysis of mechanistic insights and substrate reactivity.

Main Results:

  • Electrochemical methods enable efficient fluorination, chlorination, bromination, and iodination.
  • The review covers a range of organic substrates and reaction conditions.
  • Electrosynthesis demonstrates versatility across different carbon hybridization states.

Conclusions:

  • Electrochemical halogenation is a powerful and green approach for synthesizing halogenated organic compounds.
  • Electrosynthesis provides a sustainable and adaptable tool for modern organic synthesis.
  • Further exploration of mechanistic pathways and substrate scope is warranted.