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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.
Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
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...
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...

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Elucidating the Metabolism of 2,4-Dibromophenol in Plants
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Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Published on: February 10, 2023

4-Hydroxy-meth-yl-2-methoxy-phenol.

Qiang Wang1, Suo-Ping Li

  • 1Henan University, Kaifeng 475004, People's Republic of China.

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

This study details the crystal structure of a C(8)H(10)O(3) compound, revealing a near-planar molecule with intramolecular hydrogen bonding. Intermolecular interactions form chains within the crystal lattice.

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Area of Science:

  • Crystallography
  • Molecular structure analysis
  • Organic chemistry

Background:

  • Understanding molecular geometry is crucial in chemistry.
  • Hydrogen bonding significantly influences crystal packing and material properties.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound C(8)H(10)O(3).
  • To investigate the presence and role of intramolecular and intermolecular hydrogen bonding.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of atomic deviations from planarity and hydrogen bond geometry.

Main Results:

  • The C(8)H(10)O(3) molecule exhibits near-planarity, with a notable deviation of the hydroxyl oxygen atom.
  • An intramolecular O-H⋯O hydrogen bond was identified within the molecule.
  • Intermolecular O-H⋯O hydrogen bonds link molecules into chains propagating along the [001] direction.

Conclusions:

  • The crystal structure of C(8)H(10)O(3) is characterized by specific hydrogen bonding patterns.
  • These hydrogen bonds dictate the formation of one-dimensional chains in the solid state.