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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...

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.

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.

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...

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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: May 13, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

4-Meth-oxy-benzamidinium bromide.

Simona Irrera¹, Gustavo Portalone

¹Chemistry Department, "Sapienza" University of Rome, P.le A. Moro, 5, I-00185 Rome, Italy.

Acta Crystallographica. Section E, Structure Reports Online

|March 12, 2013

Summary

Researchers synthesized a novel salt, 4-methoxy-benzamidinium bromide, revealing unique structural properties. The crystal structure features a 3D hydrogen-bonded network, highlighting supramolecular chemistry insights.

Area of Science:

Crystallography
Supramolecular Chemistry
Organic Synthesis

Background:

Amidinium salts are important in various chemical applications.
Understanding the crystal packing and intermolecular interactions is crucial for material properties.

Purpose of the Study:

To synthesize and characterize the novel salt, 4-methoxy-benzamidinium bromide.
To investigate the crystal structure and hydrogen bonding network of the synthesized salt.

Main Methods:

Synthesis of 4-methoxy-benzamidinium bromide via reaction of 4-methoxy-benzamidine with hydro-bromic acid.
Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.

Main Results:

The synthesized salt, C8H11N2O(+)·Br(-), was obtained.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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Structural analysis revealed two similar C-N bonds in the amidinium group (1.304(2) and 1.316(2) Å).

A three-dimensional hydrogen-bonded supramolecular network was observed, with N-H(+)⋯Br(-) interactions.

Conclusions:

The study successfully synthesized and characterized 4-methoxy-benzamidinium bromide.
The crystal structure exhibits a complex hydrogen bonding network, contributing to supramolecular assembly.
The findings provide insights into the structural features and intermolecular forces in amidinium salts.