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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...
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...
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...
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...

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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2-[2-(Hydroxy-meth-yl)phen-yl]-1-phenyl-ethanol.

P Manivel, Venkatesha R Hathwar, S Mohanaroopan

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

    This study details the crystal structure of a C(15)H(16)O(2) compound, revealing specific molecular arrangements and hydrogen bonding. The research highlights intramolecular hydrogen bonds and intermolecular chains, offering insights into its solid-state structure.

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    Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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    Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

    Published on: January 3, 2018

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
    • Molecular geometry and intermolecular interactions dictate crystal packing and material behavior.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(15)H(16)O(2).
    • To analyze the dihedral angle between benzene rings, intramolecular hydrogen bonding, and intermolecular interactions.
    • To describe the observed crystal packing and molecular assembly.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, torsion angles, and non-covalent interactions was performed.
    • The crystal structure was visualized and analyzed using standard crystallographic software.

    Main Results:

    • The title compound, C(15)H(16)O(2), exhibits a dihedral angle of 19.10(5)° between its two benzene rings.
    • An intramolecular O-H⋯O hydrogen bond was identified within the molecule.
    • Molecules form extended intermolecular O-H⋯O hydrogen-bonded chains along the a axis, with observed C-H⋯π contacts.

    Conclusions:

    • The crystal structure of C(15)H(16)O(2) is characterized by specific dihedral and torsion angles, indicating a non-planar conformation.
    • Intramolecular hydrogen bonding influences the molecular conformation.
    • Intermolecular hydrogen bonding dictates the formation of 1D chains, contributing to the overall crystal architecture.