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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.
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.
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...
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.
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.

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

2-Bromo-1-(3-nitro-phen-yl)ethanone.

Jerry P Jasinski, Ray J Butcher, A S Praveen

    Acta Crystallographica. Section E, Structure Reports Online
    |April 28, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a bromine-containing nitro-ethanone compound. Analysis reveals specific molecular arrangements and intermolecular interactions, including hydrogen bonds and π-π stacking, that stabilize the 3D crystal network.

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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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    Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

    Published on: August 22, 2018

    Area of Science:

    • Crystallography
    • Chemical Physics

    Background:

    • Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
    • Nitro-ethanone derivatives are important intermediates in organic synthesis.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound C(8)H(6)BrNO(3).
    • To investigate the intermolecular interactions governing crystal packing and stability.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond distances, bond angles, and dihedral angles provided insights into molecular geometry.
    • Identification and analysis of intermolecular interactions such as hydrogen bonds, π-π stacking, and halogen bonding.

    Main Results:

    • The asymmetric unit contains two molecules (A and B) of C(8)H(6)BrNO(3).
    • Nitro and ethanone groups are nearly coplanar with the benzene ring, with slight twists observed for the bromine atom.
    • Crystal stability is maintained by a network of C-H⋯O hydrogen bonds, π-π stacking interactions, and short Br⋯O intermolecular contacts, forming a 3D supramolecular structure.

    Conclusions:

    • The crystal structure of C(8)H(6)BrNO(3) is characterized by specific orientations of functional groups and significant intermolecular interactions.
    • These interactions lead to a stable, interconnected three-dimensional network, highlighting the importance of non-covalent forces in crystal engineering.