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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.
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...
Halogens03:01

Halogens

Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group.
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.
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.
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

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Related Experiment Video

Updated: Jun 23, 2026

Probing the Structure and Dynamics of Interfacial Water with Scanning Tunneling Microscopy and Spectroscopy
10:28

Probing the Structure and Dynamics of Interfacial Water with Scanning Tunneling Microscopy and Spectroscopy

Published on: May 27, 2018

Atomic-Scale Selective C-H Halogenation Driven by Tip Electric Field in Water.

Qiang Wan1, Nan Sun1, Ling Tong1

  • 1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Key Laboratory of Advanced Catalysis and Adsorption Materials, Institute of Physical Chemistry, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua 321004, China.

Journal of the American Chemical Society
|June 21, 2026
PubMed
Summary

This study demonstrates precise atomic-level halogenation of C-H bonds using nanoconfined electric fields. This green chemistry approach offers new possibilities for synthesis and manufacturing.

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Published on: May 27, 2018

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Electrochemical Etching and Characterization of Sharp Field Emission Points for Electron Impact Ionization
06:58

Electrochemical Etching and Characterization of Sharp Field Emission Points for Electron Impact Ionization

Published on: July 12, 2016

Area of Science:

  • Chemistry
  • Materials Science
  • Physics

Background:

  • Precise control over chemical reactions at the atomic level is a key goal.
  • C-H bond functionalization is crucial for synthesizing diverse molecules.

Purpose of the Study:

  • To achieve precise atomic-level halogenation of C-H bonds.
  • To explore the use of nanoconfined electric fields for chemical transformations.

Main Methods:

  • Utilizing a scanning tunneling microscope (STM) tip to generate a nanoconfined electric field.
  • Employing in situ STM break-junction technique to study reaction kinetics.
  • Investigating the effects of electric field strength, halide concentration, and cation type on reaction rates.

Main Results:

  • Achieved precise chlorination, bromination, and iodination of α-C-H bonds in carboxylic acids at room temperature in aqueous solutions.
  • Reaction kinetics followed pseudo-first-order behavior, influenced by electric field and halide concentration.
  • Cesium (Cs+) cations significantly enhanced the reaction rate compared to sodium (Na+) cations.

Conclusions:

  • A strong confined electric field induces water dissociation, generating hydroxyl radicals for C-H bond abstraction and subsequent halogenation.
  • This work presents a precise, environmentally benign strategy for C-H bond halogenation.
  • The method holds potential for green synthesis and atomic-scale manufacturing.