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Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic Addition to Alkynes: Hydrohalogenation

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.

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

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Base-Promoted α-Halogenation of Aldehydes and Ketones

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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...

Halogenation of Alkenes

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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.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

Precipitation of Ions

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The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:

E1 Reaction: Kinetics and Mechanism

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Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...

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Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of ChalcogenidoplumbatesII or IV

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Indirect Electrosynthesis with Halogen Ions as Mediators.

Fei Lian¹, Kun Xu¹, Chengchu Zeng¹

¹Faculty of Environment and Life, Beijing University of Technology, Beijing, 100124, China.

Chemical Record (New York, N.Y.)

|March 17, 2021

Summary

This study summarizes recent advancements in halogen-mediated indirect electrosynthesis. These methods utilize halogen mediators for sustainable organic synthesis, offering an efficient alternative to traditional chemical approaches.

Keywords:

Organic electrosynthesis halogen mediator halogen radical indirect electrosynthesis

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Area of Science:

Organic Chemistry
Electrochemistry
Sustainable Synthesis

Background:

Organic electrosynthesis offers a sustainable alternative to conventional methods by using electric current as a reagent.
Indirect electrosynthesis utilizes mediators to improve reaction efficiency and substrate compatibility.
Halogen mediators are cost-efficient and versatile but often involve irreversible halogenation reactions.

Purpose of the Study:

To summarize recent developments in halogen-mediated indirect electrosynthesis.
To discuss the capabilities of anodically generated halogen species in electron-transfer (ET) and hydrogen-atom-transfer (HAT) processes.
To provide mechanistic insights and explore the scope and limitations of these reactions.

Main Methods:

Review of recent research in halogen-mediated indirect electrosynthesis.
Analysis of electron-transfer (ET) and hydrogen-atom-transfer (HAT) mechanisms.
Discussion of reaction features, scopes, and limitations.

Main Results:

Anodically generated halogen species can participate in both electron-transfer (ET) and hydrogen-atom-transfer (HAT) reactions.
Halogen-mediated indirect electrosynthesis offers enhanced efficiency and functional group compatibility.
The electrochemical reactions are influenced by halogenation processes rather than solely standard potential differences.

Conclusions:

Halogen-mediated indirect electrosynthesis is a promising area for sustainable organic synthesis.
Further research can broaden the scope and applicability of these electrochemical methods.
Understanding ET and HAT mechanisms is crucial for optimizing these reactions.