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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...

Benzene to Phenol via Cumene: Hock Process

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...

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.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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.

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...

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Related Experiment Video

Updated: Jun 1, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

N'-Diphenyl-methyl-ene-2-hydroxy-benzohydrazide.

Ning-Ning Ji, Zhi-Qiang Shi

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

A novel organic compound was synthesized and its crystal structure analyzed. Molecular analysis revealed specific hydrogen bonding patterns and a distinct dihedral angle between phenyl rings, influencing crystal packing.

Area of Science:

Organic Chemistry
Crystallography
Molecular Structure

Background:

Understanding the synthesis and structural properties of organic compounds is crucial in chemistry.
Benzohydrazide derivatives and diaryl ketones are important classes of organic molecules with diverse applications.
Elucidating intermolecular interactions, such as hydrogen bonding, is key to predicting material properties.

Purpose of the Study:

To synthesize a new organic compound C(20)H(16)N(2)O(2) from 2-hydroxy-benzohydrazide and diphenyl-methanone.
To determine the precise molecular and crystal structure of the synthesized compound.
To investigate the nature of intra- and intermolecular hydrogen bonding and its impact on crystal packing.

Main Methods:

Chemical synthesis involving the reaction of 2-hydroxy-benzohydrazide with diphenyl-methanone.

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Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

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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

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Last Updated: Jun 1, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

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Published on: November 15, 2017

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

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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

Single-crystal X-ray diffraction analysis to determine the three-dimensional structure.

Analysis of bond lengths, bond angles, dihedral angles, and hydrogen bonding interactions.

Main Results:

Successful synthesis of the title compound C(20)H(16)N(2)O(2).
The crystal structure revealed a dihedral angle of 76.28(11)° between the phenyl rings.
An intramolecular N-H⋯O hydrogen bond was observed, along with intermolecular O-H⋯O hydrogen bonds linking molecules into chains along the b axis.

Conclusions:

The study successfully synthesized and characterized a novel organic compound.
The crystal structure provides insights into the conformational preferences and hydrogen bonding capabilities of the molecule.
The observed hydrogen bonding network dictates the supramolecular architecture, forming chains in the solid state.