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Related Concept Videos

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...
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.
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...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
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...

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Related Experiment Video

Updated: Jun 1, 2026

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
09:46

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

4-(4-Fluoro-phen-oxy)benzoic acid.

Hoong-Kun Fun, Jia Hao Goh, Sankappa Rai

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

    The crystal structure of C(13)H(9)FO(3) reveals a significant dihedral angle between benzene rings. Molecules form dimers via hydrogen bonds, creating a 2D array through further intermolecular interactions.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
    • Intermolecular interactions, such as hydrogen bonding and van der Waals forces, dictate crystal packing and material behavior.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(13)H(9)FO(3).
    • To analyze the intermolecular interactions governing the crystal packing.
    • To characterize the supramolecular architecture formed in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles provided structural insights.

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  • Intermolecular interactions (O-H⋯O, C-H⋯O, C-H⋯π) were identified and analyzed using geometric criteria.

    • Main Results:

    • The crystal structure of C(13)H(9)FO(3) was determined, revealing a dihedral angle of 70.99(5)° between the two benzene rings.
    • Molecules self-assemble into centrosymmetric dimers through O-H⋯O hydrogen bonds, forming R(2)(2)(8) ring motifs.
    • These dimers are further organized into a two-dimensional array via C-H⋯O interactions, with additional weak C-H⋯π interactions observed.

    Conclusions:

    • The study provides a detailed structural characterization of C(13)H(9)FO(3) in the solid state.
    • The identified intermolecular interactions highlight the key forces driving the formation of the observed supramolecular architecture.
    • The findings contribute to the understanding of crystal engineering principles for organic molecules.