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Related Concept Videos

Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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.
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...
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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Elucidating the Metabolism of 2,4-Dibromophenol in Plants
06:54

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Published on: February 10, 2023

Bis(2-bromo-5-methyl-phen-oxy)methane.

Jun-Long Niu, Xia Wang, Lin-Bao Zhang

    Acta Crystallographica. Section E, Structure Reports Online
    |November 8, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a C15H14Br2O2 compound, revealing its molecular geometry and intermolecular bromine interactions. The findings highlight specific crystallographic features and short bromine-bromine contacts within the solid state.

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    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

    Published on: July 30, 2017

    Area of Science:

    • Crystallography
    • Solid-state chemistry
    • Organic chemistry

    Background:

    • Understanding molecular packing and intermolecular forces is crucial in solid-state chemistry.
    • Crystal structure analysis provides fundamental insights into a compound's physical and chemical properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound C15H14Br2O2.
    • To investigate the molecular geometry, including dihedral angles between aromatic rings.
    • To identify and characterize any significant intermolecular interactions, such as halogen bonding.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Crystallographic twofold symmetry was applied to generate the complete molecule.
    • Interatomic distances and angles were precisely measured.

    Main Results:

    • The complete molecule of C15H14Br2O2 was successfully generated via crystallographic twofold symmetry.
    • The central carbon atom was found to lie on the crystallographic rotation axis.
    • A dihedral angle of 62.4(3)° was measured between the two benzene rings.
    • Short bromine-bromine (Br⋯Br) contacts of 3.4885(16) Å were observed in the crystal lattice.

    Conclusions:

    • The crystal structure of C15H14Br2O2 is characterized by specific molecular symmetry and significant intermolecular Br⋯Br interactions.
    • The observed Br⋯Br contacts suggest potential halogen bonding, influencing crystal packing.
    • These findings contribute to the understanding of halogenated organic compounds in the solid state.