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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.

NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...

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.

Structure of Benzene: Kekulé Model

Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.

Nomenclature of Aromatic Compounds with Multiple Substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

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Related Experiment Video

Updated: Jun 1, 2026

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

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1,3,5-Tris(bromomethyl)benzene.

José A Fernandes¹, Sérgio M F Vilela, Paulo J A Ribeiro-Claro

¹Department of Chemistry, University of Aveiro, CICECO, 3810-193 Aveiro, Portugal.

Acta Crystallographica. Section C, Crystal Structure Communications

|June 3, 2011

Summary

This study details the crystal structure of a brominated organic compound, C(9)H(9)Br(3). Weak intermolecular forces, including bromine-bromine and carbon-hydrogen interactions, influence molecular packing and vibrational frequencies.

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Preparation of Carbon Nanosheets at Room Temperature

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Preparation of Carbon Nanosheets at Room Temperature

Preparation of Carbon Nanosheets at Room Temperature

Published on: March 8, 2016

Area of Science:

Crystallography
Organic Chemistry
Solid-State Chemistry

Background:

Understanding the packing of organic molecules is crucial for predicting material properties.
Halogenated organic compounds exhibit unique intermolecular interactions.
Crystal structure analysis provides insights into molecular behavior in the solid state.

Purpose of the Study:

To determine the crystal structure of the title compound, C(9)H(9)Br(3).
To investigate the role of weak intermolecular contacts in crystal packing.
To correlate structural findings with vibrational spectroscopy data.

Main Methods:

Single-crystal X-ray diffraction was used to elucidate the molecular and crystal structure.
Density Functional Theory (DFT) calculations were performed for comparison with experimental data.
Analysis of intermolecular interactions (Br...Br, CH...Br, CH...π) was conducted.

Main Results:

The asymmetric unit contains a single C(9)H(9)Br(3) molecule with a specific arrangement of bromine substituents.
The crystal structure is characterized by numerous weak intermolecular contacts, including Br...Br, CH(2)···Br, and CH···π interactions.
Observed red-shifts in vibrational modes of the -CH(2)Br groups are attributed to these intermolecular forces.

Conclusions:

The crystal packing of C(9)H(9)Br(3) is significantly influenced by weak intermolecular forces.
These interactions lead to observable changes in vibrational frequencies compared to theoretical predictions.
The study highlights the importance of weak interactions in dictating solid-state structures and properties.