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Related Concept Videos

Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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...
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...
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...
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.

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Related Experiment Video

Updated: May 31, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

2-Oxo-2-phenyl-ethyl benzoate.

Hoong-Kun Fun, Suhana Arshad, B Garudachari

    Acta Crystallographica. Section E, Structure Reports Online
    |July 15, 2011
    PubMed
    Summary

    This study details the crystal structure of a compound, C(15)H(12)O(3), revealing a near-perpendicular arrangement of its phenyl rings. Molecular interactions in the crystal lattice are characterized by specific hydrogen bonds, forming dimers.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding the three-dimensional arrangement of molecules in the solid state is crucial for predicting material properties.
    • Intermolecular forces, such as hydrogen bonds, play a significant role in crystal packing and the formation of supramolecular architectures.
    • The specific compound, C(15)H(12)O(3), represents a class of organic molecules with potential applications influenced by their solid-state behavior.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(15)H(12)O(3).
    • To analyze the spatial arrangement and interactions between molecules in the crystalline state.
    • To identify and characterize the intermolecular forces governing the crystal packing.

    Main Methods:

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    Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of the crystal structure included bond lengths, bond angles, and dihedral angles.
  • Intermolecular interactions, specifically hydrogen bonds, were identified and analyzed using geometric criteria.

    • Main Results:

    • The crystal structure of C(15)H(12)O(3) was successfully determined.
    • A significant dihedral angle of 86.09(9)° was observed between the terminal phenyl rings, indicating a near-orthogonal orientation.
    • A pair of intermolecular C-H⋯O hydrogen bonds were identified, linking molecules into dimers with a characteristic R(2)(2)(10) ring motif.

    Conclusions:

    • The crystal structure of C(15)H(12)O(3) exhibits a distinct conformation with highly twisted phenyl rings.
    • The formation of dimers through specific C-H⋯O hydrogen bonds is a key feature of the crystal packing.
    • These findings contribute to the understanding of structure-property relationships in organic crystalline materials.