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Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...

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...

Reactions at the Benzylic Position: Oxidation and Reduction

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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...

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 5, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

N'-(2-Hydroxy-benzyl-idene)-4-methoxy-benzohydrazide.

Chun-Bao Tang¹

¹Department of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

This study details a new Schiff base compound synthesized from salicylaldehyde and 4-methoxy-benzohydrazide. Its crystal structure reveals specific molecular arrangements and hydrogen bonding, offering insights into Schiff base chemistry.

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Last Updated: Jun 5, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

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Published on: July 17, 2020

Area of Science:

Organic Chemistry
Crystallography
Supramolecular Chemistry

Background:

Schiff bases are versatile organic compounds with diverse applications.
Understanding the structural properties of Schiff bases is crucial for designing new materials.

Purpose of the Study:

To synthesize and characterize a novel Schiff base compound.
To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

Condensation reaction between salicylaldehyde and 4-methoxy-benzohydrazide.
Single crystal X-ray diffraction analysis to determine molecular and crystal structure.

Main Results:

The Schiff base compound C(15)H(14)N(2)O(3) was successfully synthesized.
The crystal structure analysis revealed a dihedral angle of 2.5(2)° between the benzene rings.
Intermolecular N-H⋯O hydrogen bonds were observed, forming chains along the b axis.

Conclusions:

The study successfully synthesized and structurally characterized a new Schiff base.
The findings provide valuable data on the solid-state structure and hydrogen bonding capabilities of this Schiff base.