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Related Concept Videos

Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
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.
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...
Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
Benzene to Phenol via Cumene: Hock Process01:27

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...
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...

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

Published on: November 15, 2017

2-Meth-oxy-3,4-diphenyl-phenol.

Ilia A Guzei1, Senthilvelan Annamalai, Howard E Zimmerman

  • 1Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

A novel organic compound was synthesized via solid-state photochemistry. Its crystal structure reveals specific dihedral angles and hydrogen-bonded dimers, offering insights into molecular packing and reactivity.

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Area of Science:

  • Organic Chemistry
  • Solid-State Chemistry
  • Photochemistry

Background:

  • Photochemical reactions offer unique pathways for synthesizing complex organic molecules.
  • Understanding molecular structure and intermolecular interactions is crucial for predicting chemical behavior.

Purpose of the Study:

  • To isolate and characterize the major product from the solid-state photochemical reaction of 2-methoxy-4,4-diphenyl-cyclohexa-2,5-dienone.
  • To elucidate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

  • Solid-state photochemical reaction.
  • Single-crystal X-ray diffraction analysis using a Bruker SMART X2S diffractometer.
  • Data collection at room temperature and manual processing.

Main Results:

  • Isolation of C(19)H(16)O(2) as the major product.
  • Determination of dihedral angles between the central ring and pendant benzene rings (60.76° and 51.64°).
  • Identification of hydrogen-bonded dimers formed via O-H⋯O interactions and a specific torsion angle (94.89°) for the methoxy group.

Conclusions:

  • The solid-state photochemical reaction provides an efficient route to the target compound.
  • The crystal structure reveals specific conformational preferences and intermolecular interactions.
  • These findings contribute to the understanding of structure-property relationships in organic solids.