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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

18.2K
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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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.3K
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...
6.3K
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

3.3K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
3.3K
Alkyl Halides02:45

Alkyl Halides

19.3K
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...
19.3K
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

7.3K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
7.3K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.2K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.2K

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Updated: Dec 25, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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In Situ Synthesis and Applications for Polyinterhalides Based on BrCl.

Benjamin Schmidt1, Sebastian Ponath2, Johannes Hannemann1

  • 1Fachbereich Biologie, Chemie, Pharmazie, Institut für Chemie und Biochemie-Anorganische Chemie, Fabeckstr. 34/36, 14195, Berlin, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 7, 2020
PubMed
Summary

Researchers developed novel reactive ionic liquids to stabilize bromine chloride (BrCl), making this potent chemical safer and easier to handle for organic and inorganic chemistry applications.

Keywords:
bromine monochloridehalogen bondinghalogenationpolyhalides

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Area of Science:

  • Chemistry
  • Materials Science

Background:

  • Bromine chloride (BrCl) is a valuable reagent in chemistry.
  • Its gaseous state and decomposition into chlorine (Cl2) and bromine (Br2) limit its practical applications.

Purpose of the Study:

  • To stabilize BrCl using reactive ionic liquids.
  • To develop safer and more manageable interhalogenation reagents.

Main Methods:

  • In situ synthesis of BrCl-based ionic liquids.
  • Characterization using single-crystal X-ray diffraction (XRD).
  • Spectroscopic analysis (Raman and IR).
  • Quantum chemical calculations.

Main Results:

  • Successfully stabilized BrCl in ionic liquid form, shifting the equilibrium towards BrCl.
  • Synthesized and characterized novel crystalline anions: [Cl(BrCl)2]- and [Cl(BrCl)4]-.
  • Demonstrated improved handling and safety of BrCl reagents.

Conclusions:

  • Reactive ionic liquids provide an effective method for stabilizing BrCl.
  • This stabilization enhances the utility of BrCl as an interhalogenation reagent.
  • The newly synthesized anions represent a significant advancement in halogen chemistry.