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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

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Published on: January 21, 2020

2-Methyl-4-nitro-phenol.

Sheng Bi, Yong-Zhong Wu, Yi-Xin Zhou

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

The crystal structure of C(7)H(7)NO(3) reveals a nearly planar molecule. Intermolecular interactions create a robust three-dimensional network in the solid state.

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Area of Science:

Crystallography
Solid-state chemistry
Molecular structure

Background:

Understanding molecular arrangement in crystals is key to predicting material properties.
The title compound, C(7)H(7)NO(3), is of interest for its potential applications.

Purpose of the Study:

To elucidate the crystal structure of C(7)H(7)NO(3).
To investigate the intermolecular interactions governing the solid-state packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of non-covalent interactions, including hydrogen bonds and C-H⋯O interactions, was performed.

Main Results:

The molecule of C(7)H(7)NO(3) exhibits a nearly planar conformation, with a maximum deviation of 0.112(3) Å for a nitro oxygen atom.
The crystal packing is characterized by a three-dimensional network formed through intermolecular O-H⋯O and C-H⋯O interactions.

Conclusions:

The study provides detailed structural insights into C(7)H(7)NO(3).
The identified intermolecular interactions are crucial for the observed three-dimensional network, influencing the compound's solid-state behavior.