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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...
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...
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.
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...
Benzene to Phenol via Cumene: Hock Process01:27

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...
IUPAC Nomenclature of Aldehydes01:16

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...

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Related Experiment Video

Updated: May 26, 2026

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

Published on: August 16, 2018

2-(2-Benzyl-phen-yl)propan-2-ol.

Richard Betz, Thomas Gerber, Eric Hosten

    Acta Crystallographica. Section E, Structure Reports Online
    |December 27, 2011
    PubMed
    Summary

    This study describes a tertiary alcohol, C(16)H(18)O, with a unique 2-benzyl-phenyl group. Molecules of this compound self-assemble into stable tetra-mers through hydrogen bonding.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Supramolecular Chemistry

    Background:

    • Tertiary alcohols are versatile organic compounds with diverse applications.
    • Understanding molecular assembly is crucial for designing new materials.
    • Hydrogen bonding plays a key role in the self-assembly of organic molecules.

    Purpose of the Study:

    • To characterize the crystal structure of a novel tertiary alcohol, C(16)H(18)O.
    • To investigate the intermolecular interactions governing the self-assembly of this compound.
    • To elucidate the role of hydrogen bonding in the formation of molecular aggregates.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of hydrogen bonding networks was performed using crystallographic data.

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    Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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    Published on: August 16, 2018

    Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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    Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

    Published on: October 30, 2018

  • The stoichiometry of the hydrogen-bonded assemblies was identified.

    • Main Results:

    • The asymmetric unit contains two molecules of the title compound, C(16)H(18)O.
    • The compound is a tertiary alcohol featuring a 2-benzyl-phenyl substituent.
    • Co-operative O-H⋯O hydrogen bonds link the molecules into tetra-mers.

    Conclusions:

    • The crystal structure reveals a novel tertiary alcohol with potential applications in organic synthesis.
    • The formation of tetra-mers via hydrogen bonding highlights the importance of intermolecular forces in molecular organization.
    • This study provides insights into the supramolecular chemistry of substituted tertiary alcohols.