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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.

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...

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...

Physical Properties of Alcohols and Phenols

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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 Process

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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...

Reactions at the Benzylic Position: Halogenation

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.

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Related Experiment Video

Updated: May 13, 2026

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1-(10H-phenothia-zin-10-yl)ethanone.

Eri Tokunaga¹, Tsunehisa Okuno

¹Department of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan.

Acta Crystallographica. Section E, Structure Reports Online

|March 12, 2013

Summary

The phenothiazine compound exhibits a butterfly conformation with a boat-shaped central ring. A larger fold angle, attributed to steric hindrance, was observed between its benzene rings.

Area of Science:

Organic chemistry
Crystallography
Molecular structure

Background:

Phenothiazine derivatives are known for their diverse applications.
Understanding the molecular conformation is crucial for predicting chemical properties and biological activity.
The specific compound C14H11NOS presents an interesting case for structural analysis.

Purpose of the Study:

To elucidate the three-dimensional molecular structure of the title compound, C14H11NOS.
To analyze the conformation of the phenothiazine unit and the central six-membered ring.
To investigate the factors influencing the observed fold angle between the benzene rings.

Main Methods:

Single-crystal X-ray diffraction analysis was employed.
The molecular geometry and conformation were determined.

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Comparison with similar phenothiazine structures was performed.

Main Results:

The phenothiazine unit adopts a butterfly conformation.
The central six-membered ring is in a boat form.
A fold angle of 46.39(7)° was measured between the benzene rings, larger than in related compounds.

Conclusions:

The observed butterfly conformation and boat-shaped central ring are key structural features.
The increased fold angle is likely due to steric repulsion from the acetyl group.
This detailed structural information provides insights into the chemical behavior of this phenothiazine derivative.