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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...
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.
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

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Related Experiment Video

Updated: Jun 1, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

4-Bromo-4'-(dimethyl-amino)stilbene.

Rodolfo Moreno-Fuquen, Alan R Kennedy, Cristina Cordoba

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

    The crystal structure of C(16)H(16)BrN reveals a unique molecular geometry. Benzene rings are inclined at 50.5 degrees, and the carbon-carbon double bond is in a cis conformation.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Brominated organic compounds are important intermediates in various chemical syntheses.

    Purpose of the Study:

    • To determine the precise molecular geometry of the title compound, C(16)H(16)BrN.
    • To characterize the spatial relationship between the benzene rings and the conformation of the C=C bond.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to elucidate the solid-state structure.
    • The dihedral angle between the mean planes of the benzene rings was measured.
    • The conformation of the central C=C bond was identified.

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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

    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
    04:38

    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

    Published on: July 28, 2022

    Related Experiment Videos

    Last Updated: Jun 1, 2026

    Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
    08:56

    Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

    Published on: November 30, 2022

    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
    19:58

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

    Published on: July 30, 2017

    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
    04:38

    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

    Published on: July 28, 2022

    Main Results:

    • The crystal structure of C(16)H(16)BrN was successfully determined.
    • A significant dihedral angle of 50.5(3)° was observed between the two benzene rings.
    • The C=C double bond was found to adopt a cis conformation.

    Conclusions:

    • The title compound exhibits a non-planar structure with significantly inclined benzene rings.
    • The cis conformation of the C=C bond influences the overall molecular shape and potential intermolecular interactions.
    • This structural data provides a foundation for further studies on the reactivity and properties of this brominated organic molecule.