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Related Concept Videos

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.
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.
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.
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.
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...

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Related Experiment Video

Updated: May 11, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Pentane-1,5-diaminium dibromide.

Charmaine Arderne1

  • 1Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, Johannesburg 2006, South Africa. carderne@uj.ac.za

Acta Crystallographica. Section C, Crystal Structure Communications
|May 1, 2013
PubMed
Summary

Researchers determined the crystal structure of a novel ammonium bromide salt. The study revealed complex hydrogen bonding and organic-inorganic layering, with disordered cation chains.

Area of Science:

  • Crystallography
  • Materials Science
  • Chemical Physics

Background:

  • Ammonium bromide salts represent a unique class of compounds with diverse structural properties.
  • Understanding the crystal structure of such salts is crucial for predicting their physical and chemical behavior.
  • The Cambridge Structural Database contains limited examples of ammonium bromide salts, highlighting the novelty of this study.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the C5H16N2(2+)·2Br(-) salt.
  • To investigate the packing arrangement, including organic-inorganic layering and hydrogen bonding.
  • To analyze the nature and strength of the identified hydrogen bonds.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

  • The crystal structure was analyzed for molecular arrangement, including cation chains and their potential disorder.
  • Disorder modeling was utilized to accurately represent the positional disorder in the diaminium cation chains.
  • Analysis of intermolecular interactions, specifically hydrogen bonding and layering, was performed.

    • Main Results:

    • The crystal structure of C5H16N2(2+)·2Br(-) was determined, revealing a complex arrangement with Z = 12 and Z' = 3.
    • Positional disorder was observed and successfully modeled in one of the diaminium cation chains.
    • The packing arrangement exhibited characteristic organic-inorganic layering typical of ammonium bromide salts.
    • An extensive three-dimensional hydrogen-bonding network was identified, primarily composed of strong charge-assisted hydrogen bonds.

    Conclusions:

    • The crystal structure of this ammonium bromide salt is characterized by unique features including high multiplicity and cation disorder.
    • The observed organic-inorganic layering and complex hydrogen-bonding network provide insights into the structure-property relationships of this class of compounds.
    • The identification of strong charge-assisted hydrogen bonds suggests significant electrostatic contributions to the overall crystal stability.