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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...

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.

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...

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...

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...

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Related Experiment Video

Updated: Jun 1, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

2-(4H-1,2,4-Triazol-4-yl)phenol.

Wang Zhao, Wei-Wei Zhou, Ming-Jun Song

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This study details the molecular structure of a specific organic compound, C(8)H(7)N(3)O. The research highlights a significant dihedral angle of 41.74 degrees between its benzene and triazole rings.

Area of Science:

Organic Chemistry
Crystallography
Molecular Structure

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial.
The spatial relationship between aromatic and heterocyclic rings influences chemical properties and reactivity.

Purpose of the Study:

To determine the precise molecular geometry of the compound C(8)H(7)N(3)O.
To quantify the dihedral angle between the constituent benzene and triazole rings.

Main Methods:

Single-crystal X-ray diffraction was employed to analyze the crystal structure.
The dihedral angle was calculated from the atomic coordinates obtained through diffraction.

Main Results:

The crystal structure of C(8)H(7)N(3)O was successfully elucidated.

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

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A dihedral angle of 41.74(12)° was measured between the benzene and triazole ring systems.

Conclusions:

The non-planar conformation, characterized by the measured dihedral angle, is a key feature of this molecule.
This structural information provides a foundation for further studies on the compound's chemical behavior and potential applications.