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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...

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: 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.

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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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: Jun 1, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

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Published on: October 24, 2017

9-Benzyl-3-bromo-9H-carbazole.

Peng-Mian Huang, Xiao-Chun Wang

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

A novel N-alkylated carbazole derivative was synthesized. Structural analysis revealed a nearly planar carbazole ring system with a significant dihedral angle relative to the phenyl ring.

Area of Science:

Organic Chemistry
Crystallography
Materials Science

Background:

Carbazole derivatives are important scaffolds in organic electronics and medicinal chemistry.
Understanding the three-dimensional structure of novel carbazole compounds is crucial for predicting their properties and applications.

Purpose of the Study:

To synthesize a new N-alkylated carbazole compound.
To elucidate the solid-state structure of the synthesized compound using X-ray crystallography.

Main Methods:

N-alkylation reaction between (chloro-methyl)benzene and 3-bromo-9H-carbazole.
Single-crystal X-ray diffraction analysis to determine molecular and crystal structure.

Main Results:

Successful synthesis of the target compound, C(19)H(14)BrN.

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

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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

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Published on: July 30, 2017

The carbazole moiety exhibits near planarity with a root-mean-square deviation of 0.013 Å.

A dihedral angle of 87.1(2)° was observed between the carbazole and phenyl rings.

Conclusions:

The synthesis yielded a novel N-alkylated carbazole.
The determined crystal structure provides insights into the spatial arrangement of the carbazole and phenyl rings, relevant for designing functional organic materials.