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Related Concept Videos

Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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...
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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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...

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2,4-Dinitro-1-phenoxy-benzene.

Zhen-Ting Du1, Yan Xu, Hong-Rui Yu

  • 1College of Science, Northwest A&F University, Yangling Shaanxi 712100, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel compound, C(12)H(8)N(2)O(5), through a chemical reaction. The study details its unique molecular structure and crystal packing, revealing an orthogonal relationship between its aromatic rings.

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Structure

Background:

  • Understanding the synthesis and structural properties of novel organic compounds is crucial in chemistry.
  • Aromatic compounds with nitro-substituents often exhibit interesting electronic and structural characteristics.

Purpose of the Study:

  • To synthesize and characterize a new compound with the molecular formula C(12)H(8)N(2)O(5).
  • To elucidate the molecular structure and crystal packing of the synthesized compound.
  • To investigate the spatial relationship between the aromatic rings within the molecule.

Main Methods:

  • Chemical synthesis involving the reaction of 1-chloro-2,4-dinitro-benzene and phenol.
  • Use of potassium carbonate as a catalyst or base.
  • X-ray crystallography for determining the solid-state structure.
  • Analysis of molecular geometry and crystal packing.

Main Results:

  • Successful synthesis of the title compound, C(12)H(8)N(2)O(5).
  • The nitro-substituted benzene ring was found to lie on a mirror plane, with one nitro group in-plane and the other disordered.
  • The phenoxy-benzene unit adopted a perpendicular orientation relative to the mirror plane.
  • An orthogonal relationship was observed between the phenyl and benzene rings.
  • Crystal packing analysis revealed no significant intermolecular contacts.

Conclusions:

  • The study successfully synthesized and characterized a novel organic compound.
  • The molecular structure features a distinct orthogonal arrangement of aromatic rings.
  • The crystal packing does not indicate strong intermolecular interactions, suggesting potential for further derivatization or unique solid-state behavior.