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Structure and Nomenclature of Alcohols and Phenols

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...

Oxidation of Phenols to Quinones

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 Phenols

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...

Acidity and Basicity of Alcohols and Phenols

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.

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...

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Semi-Targeted Ultra-High-Performance Chromatography Coupled to Mass Spectrometry Analysis of Phenolic Metabolites in Plasma of Elderly Adults

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3,4,5-Trimeth-oxy-phenol.

Xiao-Chuan Jia¹, Jing Li, Zhi-Rui Yu

¹Tianjin Entry-Exit Inspection and Quarantine Bureau, Tianjin 300201, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|January 4, 2013

Summary

This summary is machine-generated.

This study details the crystal structure of C(9)H(12)O(4), revealing two independent molecules with similar planar conformations. Hydrogen bonds and C-H interactions stabilize the three-dimensional crystal lattice.

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Area of Science:

Crystallography
Molecular structure analysis
Supramolecular chemistry

Background:

Understanding molecular arrangements in the solid state is crucial for predicting material properties.
Crystal structure determination provides fundamental insights into intermolecular forces.

Purpose of the Study:

To elucidate the three-dimensional crystal structure of the title compound, C(9)H(12)O(4).
To analyze the molecular conformation and intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.
Analysis of bond lengths, bond angles, torsion angles, and intermolecular interactions (hydrogen bonds, C-H⋯O, C-H⋯π).

Main Results:

The asymmetric unit contains two crystallographically independent molecules of C(9)H(12)O(4) with similar conformations.
Molecules exhibit near-planar arrangements, deviating primarily at the methoxy-methyl group (torsion angles of 83.3(2)° and 83.9(2)°).
O-H⋯O hydrogen bonds form supramolecular chains along the b-axis, further stabilized by C-H⋯O and C-H⋯π interactions.

Conclusions:

The crystal structure of C(9)H(12)O(4) is characterized by specific molecular conformations and a network of intermolecular interactions.
Hydrogen bonding and van der Waals forces play significant roles in stabilizing the observed three-dimensional crystal architecture.