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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...

Radical Halogenation: Thermodynamics

Radical Halogenation: Thermodynamics

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...

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...

Hybridization of Atomic Orbitals I

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

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.

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Related Experiment Video

Updated: Jul 6, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

High-pressure stabilization of open-shell bromine fluorides.

Madhavi H Dalsaniya^1,2, Deepak Upadhyay², Krzysztof Jan Kurzydłowski¹

¹Faculty of Materials Science and Engineering, Warsaw University of Technology, 02-507 Warsaw, Poland. madhavi.dalsaniya.dokt@pw.edu.pl.

Physical Chemistry Chemical Physics : PCCP

|January 2, 2024

Summary

High pressure transforms bromine fluorides, creating novel stable compounds BrF2 and BrF6. Molecular orbital theory and VSEPR models explain their unique properties under extreme conditions.

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Last Updated: Jul 6, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

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Area of Science:

Chemistry
Materials Science
Computational Chemistry

Background:

Halogen fluorides typically illustrate molecular orbital theory and VSEPR models.
Applicability of these models to high-pressure compounds remains an open question.

Purpose of the Study:

Investigate phase transitions and reactivity of bromine fluorides under high pressure (>1 GPa).
Explore the behavior of bromine-fluorine systems up to 100 GPa.

Main Methods:

Computational study of bromine fluoride phase transitions.
Thermodynamic stability analysis of compounds at high pressures.

Main Results:

Bromine trifluoride (BrF3) becomes unstable at 15 GPa.
Two new stable compounds, BrF2 and BrF6, emerge at high pressures.
These novel compounds are predicted to be non-metallic and contain radical molecules.

Conclusions:

Fundamental chemical concepts remain applicable to understanding high-pressure compounds.
Predicts novel stable bromine fluoride species and a potential synthetic route for BrF2.