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Related Concept Videos

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.
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...
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...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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...
Protection of Alcohols02:31

Protection of Alcohols

This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...

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Related Experiment Video

Updated: Jun 1, 2026

Microwave-Assisted Extraction of Phenolic Compounds and Antioxidants for Cosmetic Applications Using Polyol-Based Technology
07:05

Microwave-Assisted Extraction of Phenolic Compounds and Antioxidants for Cosmetic Applications Using Polyol-Based Technology

Published on: August 23, 2024

4-Ethyl-phenol.

Richard Betz1, Peter Klüfers, Peter Mayer

  • 1Ludwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13 (Haus D), 81377 München, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of a compound C(8)H(10)O, revealing how molecules connect via hydrogen bonds. These bonds form specific chains, described using graph theory descriptors for structural analysis.

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Chemical Physics

Background:

  • Understanding molecular arrangement in crystals is key to predicting material properties.
  • Hydrogen bonding plays a crucial role in the self-assembly of molecules.
  • Graph theory provides a framework for describing complex structural patterns.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(8)H(10)O.
  • To analyze the hydrogen bonding network and its role in molecular assembly.
  • To characterize the observed structural pattern using graph-theoretical descriptors.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the crystal structure.
  • Analysis of intermolecular interactions, specifically O-H⋯O hydrogen bonds.

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  • Application of graph theory to describe the hydrogen bond network topology.

    • Main Results:

    • The title compound, C(8)H(10)O, crystallizes with three molecules in the asymmetric unit.
    • Cooperative O-H⋯O hydrogen bonds form chains along the [100] direction.
    • The hydrogen bonding pattern was assigned a DDD descriptor on the unitary graph level and a C(3)(3)(6) ternary descriptor.

    Conclusions:

    • The crystal structure reveals a specific chain-like assembly driven by hydrogen bonding.
    • Graph theory descriptors provide a concise and systematic way to classify the observed supramolecular architecture.
    • This detailed structural analysis contributes to the understanding of crystal engineering principles.