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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 Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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...

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

Reactions at the Benzylic Position: Halogenation

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

Formation of Halohydrin from Alkenes

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

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2-(2,4,6-Trichloro-phen-oxy)ethyl bromide.

Jin-Feng Yao, Wen-Ge Yang, Xiao-Lei Zhao

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a brominated and chlorinated organic compound, C(8)H(6)BrCl(3)O. It reveals a weak intramolecular hydrogen bond and intermolecular chlorine-chlorine contacts, offering insights into chemical bonding and crystal packing.

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Area of Science:

Crystallography
Organic Chemistry
Solid-State Chemistry

Background:

Understanding the crystal structure of halogenated organic compounds is crucial for predicting their physical and chemical properties.
Intramolecular interactions and intermolecular contacts significantly influence molecular packing and reactivity.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(8)H(6)BrCl(3)O.
To identify and characterize intra-molecular and inter-molecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional arrangement of atoms.
Analysis of bond lengths, bond angles, and non-bonded contacts was performed.

Main Results:

The crystal structure revealed the presence of a weak intramolecular C-H⋯Cl hydrogen bond involving the methylene group attached to oxygen.
Significant intermolecular Cl⋯Cl contacts with a distance of 3.482(2) Å were identified, indicating specific packing arrangements.

Conclusions:

The identified hydrogen bond and Cl⋯Cl contacts provide valuable data on the intermolecular forces governing the crystal packing of this halogenated compound.
These findings contribute to the broader understanding of halogen bonding and crystal engineering in organic solids.