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Related Concept Videos

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...
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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.
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.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Related Experiment Video

Updated: May 26, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

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Published on: January 19, 2016

4-Methyl-phenyl 4-bromo-benzoate.

Rodolfo Moreno-Fuquen, Javier Ellena, Carlos A De Simone

    Acta Crystallographica. Section E, Structure Reports Online
    |January 6, 2012
    PubMed
    Summary

    This study details the crystal structure of a novel ester formed from 4-methyl-phenol and 4-bromo-benzoyl-chloride. Molecular analysis reveals a twisted structure with specific intermolecular interactions influencing crystal packing.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Supramolecular Chemistry

    Background:

    • Esters are versatile organic compounds with diverse applications.
    • Understanding molecular structure and intermolecular forces is key to predicting material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the ester formed from 4-methyl-phenol and 4-bromo-benzoyl-chloride.
    • To investigate the intermolecular interactions governing crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond distances, angles, and non-covalent interactions (C-H⋯O, Br⋯Br) was performed.

    Main Results:

    • The synthesized ester, C(14)H(11)BrO(2), exhibits a significant dihedral angle (54.43°) between its benzene rings, indicating molecular twisting.

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  • Supramolecular layers are formed via weak C-H⋯O interactions in the bc plane.
  • These layers are further interconnected along the a axis by Br⋯Br contacts (3.6328 Å).

    • Conclusions:

    • The crystal structure reveals a twisted molecular conformation driven by steric and electronic factors.
    • The identified intermolecular interactions (C-H⋯O and Br⋯Br) dictate the overall supramolecular architecture and crystal packing.
    • This structural insight contributes to the understanding of ester-based crystal engineering.