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Radical Halogenation: Thermodynamics

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The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
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Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

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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...
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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.
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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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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...
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Recent developments in electrochemical halogenation and dehalogenation reactions.

Malkeet Singh1, Saurabh Singh1, Maya Shankar Singh1

  • 1Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi-211005, India. mayashankarbhu@gmail.com.

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Summary

This review explores green electrochemical methods for synthesizing organohalides, crucial for pharmaceuticals. It covers electrochemical halogenation and dehalogenation, including cross-coupling reactions, offering sustainable synthetic strategies.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Electrochemistry

Background:

  • Organohalides are essential building blocks in synthesizing valuable molecules, particularly for pharmaceutical applications.
  • Developing novel, environmentally friendly synthetic methods for organohalides is a significant area of research.
  • Electrochemical synthesis presents a sustainable and economically viable approach to chemical production.

Purpose of the Study:

  • To review recent advancements in synthetic electrochemistry for organohalide synthesis.
  • To highlight electrochemical halogenation using diverse electrolytes and halogen sources.
  • To discuss electrochemical dehalogenation, including cross-coupling and substitution reactions.

Main Methods:

  • Summarizing recent literature on electrochemical halogenation reactions.
  • Reviewing studies on electrochemical dehalogenation processes.
  • Analyzing the use of various electrolytes and organohalides as halogen sources.

Main Results:

  • Electrochemical methods offer efficient and green routes for organohalide synthesis.
  • Electrochemical halogenation enables the use of various halogen sources and electrolytes.
  • Electrochemical dehalogenation facilitates cross-coupling and substitution reactions.

Conclusions:

  • Synthetic electrochemistry provides powerful tools for accessing organohalides sustainably.
  • Electrochemical halogenation and dehalogenation are key strategies for green organic synthesis.
  • This review consolidates recent progress, paving the way for future electrochemical applications.