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Halogenation of Alkenes

Halogenation of Alkenes

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.

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

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

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

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.

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 HX to 1,3-Butadiene

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

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Alkyl Halides

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Recent Advances in Halogen Bonded Assemblies with Resorcin[4]arenes.

Kwaku Twum¹, Kari Rissanen², Ngong Kodiah Beyeh¹

¹Oakland University, Department of Chemistry, 146 Library Drive, Rochester, 48309, Michigan, USA.

Chemical Record (New York, N.Y.)

|December 28, 2020

Summary

Resorcinarene macrocycles form unique assemblies using halogen bonding (XB). This review highlights recent advances in discrete and capsular structures built from these versatile compounds and their derivatives.

Keywords:

capsules cavitands discrete assemblies halogen bond resorcinarenes

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Crystal Engineering

Background:

Resorcinarenes are macrocyclic compounds with inherent cavity-forming properties, belonging to the calixarene family.
Their structure allows for functionalization at multiple positions, making them versatile building blocks.
Supramolecular chemistry utilizes weak interactions to create complex molecular assemblies.

Purpose of the Study:

To provide an overview of recent advancements in halogen-bonded (XB) assemblies utilizing resorcinarenes.
To focus specifically on the formation of discrete and capsular supramolecular structures.
To highlight the role of resorcinarene derivatives in XB-driven self-assembly.

Main Methods:

Synthesis of functionalized resorcinarene derivatives.
Utilizing halogen bonding as a primary non-covalent interaction for assembly.
Characterization of discrete and capsular supramolecular architectures.

Main Results:

Resorcinarenes act as effective platforms for constructing XB-driven supramolecular assemblies.
Discrete and capsular structures are successfully formed through tailored resorcinarene derivatives.
Halogen bonding enables precise control over the assembly of resorcinarene-based systems.

Conclusions:

Resorcinarenes are valuable synthons for creating sophisticated supramolecular architectures via halogen bonding.
The review underscores the potential of resorcinarene-XB interactions in designing functional materials.
Further exploration of these assemblies can lead to novel applications in molecular recognition and materials science.