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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.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

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...

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.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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.

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Related Experiment Video

Updated: Jun 5, 2026

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

3-Bromo-N'-[(E)-4-hydroxy-benzyl-idene]benzohydrazide.

Tao Yang¹, Guo-Biao Cao, Ji-Ming Xiang

¹Department of Chemistry, Ankang University, Ankang, Shanxi 725000, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

Researchers synthesized a novel compound, C(14)H(11)BrN(2)O(2), using 4-hydroxy-benzaldehyde and 3-bromo-benzohydrazide. The crystal structure reveals a unique 3D network formed by intermolecular hydrogen bonds.

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Area of Science:

Organic Chemistry
Crystallography
Supramolecular Chemistry

Background:

Hydrazide derivatives are important in medicinal chemistry and materials science.
Understanding molecular interactions in crystal structures is key to designing new materials.

Purpose of the Study:

To synthesize and characterize a novel organic compound with potential applications.
To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

Synthesis of the title compound via condensation reaction.
Single crystal X-ray diffraction analysis to determine molecular and crystal structure.
Analysis of intermolecular interactions, including hydrogen bonding.

Main Results:

Successful synthesis of the compound C(14)H(11)BrN(2)O(2).
The crystal structure exhibits a dihedral angle of 40.1° between the two benzene rings.
Molecules form a 3D network through O-H⋯O, O-H⋯N, and N-H⋯O hydrogen bonds.

Conclusions:

The synthesized compound possesses a defined molecular geometry and packing arrangement.
Intermolecular hydrogen bonding plays a crucial role in stabilizing the crystal lattice.
The study provides insights into the structure-property relationships of bromo-benzohydrazide derivatives.