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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.

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...

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.

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...

Radical Halogenation: Stereochemistry

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:

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.

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Related Experiment Video

Updated: May 11, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

3-Bromo-chroman-4-one.

Mahidansha M Shaikh¹, Neil A Koorbanally, Karen Du Toit

¹School of Chemistry and Physics, University of Kwazulu-Natal, Private Bag X54001, Durban 4000, South Africa.

Acta Crystallographica. Section E, Structure Reports Online

|May 2, 2013

Summary

This summary is machine-generated.

Bromination of 4-chromanone yielded a novel compound with a half-chair conformation. Its crystal structure reveals weak C-H⋯O hydrogen bonding and π-π stacking interactions between benzene rings.

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Last Updated: May 11, 2026

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Area of Science:

Organic Chemistry
Crystallography
Supramolecular Chemistry

Background:

4-Chromanone is a key heterocyclic scaffold in medicinal chemistry.
Understanding the conformational and supramolecular properties of its derivatives is crucial for drug design.
Bromination is a common synthetic route to introduce functional groups and modify molecular properties.

Purpose of the Study:

To synthesize and characterize a novel brominated 4-chromanone derivative.
To elucidate the conformational preferences of the heterocyclic ring.
To investigate the intermolecular interactions governing the crystal packing.

Main Methods:

Synthesis of the title compound (C9H7BrO2) via bromination of 4-chromanone using copper bromide.
Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
Analysis of non-covalent interactions, including hydrogen bonding and π-π stacking.

Main Results:

The title compound was successfully synthesized and its structure elucidated.
The heterocyclic ring adopts a half-chair conformation.
The supramolecular assembly is characterized by a weak C-H⋯O hydrogen bond.
Significant π-π stacking interactions were observed between adjacent benzene rings with specific geometric parameters (centroid-centroid distance, perpendicular distance, and offset).

Conclusions:

The study provides insights into the conformational flexibility of brominated chromanone derivatives.
The identified supramolecular interactions highlight the importance of non-covalent forces in crystal engineering.
The findings contribute to the understanding of structure-property relationships in heterocyclic compounds.