Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

18.4K
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.
18.4K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

10.7K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
10.7K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

14.6K
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.
14.6K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.5K
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...
6.5K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

9.8K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
9.8K
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

10.1K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
10.1K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Visible Light-Induced Intermolecular Dearomatization for Constructing Angularly Fused Tetracyclic Scaffolds.

Nature communications·2026
Same author

Pyridyl Radical-Induced Catalytic Reconstruction of Cyclic Sulfides.

Journal of the American Chemical Society·2026
Same author

Phosphine-Catalyzed Unsymmetric [2 + 2] Annulation of Allenyl Phosphonates for Highly Substituted Cyclobutenes.

Angewandte Chemie (International ed. in English)·2026
Same author

Palladium-Catalyzed Regiodivergent Telomerization of Isoprene With Oxindoles.

Angewandte Chemie (International ed. in English)·2026
Same author

Regiodivergent 1,3-Annulation of Valylene with 4-Hydroxycoumarins.

Organic letters·2026
Same author

Chemodivergent Coupling of 1,3-Enynes with Anilines to Access Dihydropyrrole Skeleton under Palladium Catalysis.

Nature communications·2026

Related Experiment Video

Updated: Jan 17, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.7K

Electrochemically driven bromochlorination of alkenes.

Chang-Hui Liu1,2, Su-Yang Xu1,2, Xue-Ting Li1,2

  • 1Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China. hzheng@dicp.ac.cn.

Chemical Communications (Cambridge, England)
|September 25, 2025
PubMed
Summary

Researchers developed a novel electrochemical method for selective bromochlorination of alkenes. This green chemistry approach offers precise halogenation under mild conditions, avoiding harsh reagents.

More Related Videos

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.7K
Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

6.9K

Related Experiment Videos

Last Updated: Jan 17, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.7K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.7K
Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

6.9K

Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Green Chemistry

Background:

  • Organic halides are crucial building blocks in synthesizing pharmaceuticals, agrochemicals, and advanced materials.
  • Traditional alkene dihalogenation methods often rely on active halogen reagents, which can pose safety and environmental concerns.

Purpose of the Study:

  • To develop a novel electrochemical strategy for the selective synthesis of organic halides.
  • To establish a milder and more precise method for alkene bromochlorination compared to conventional techniques.

Main Methods:

  • Electrochemical synthesis was employed to achieve selective bromochlorination.
  • The reaction conditions were optimized for mildness and efficiency.

Main Results:

  • The developed electrochemical method demonstrated high selectivity for bromochlorination of alkenes.
  • Precise control over halogenation was achieved under mild reaction conditions.

Conclusions:

  • This study presents a viable and sustainable electrochemical alternative for producing valuable organic halides.
  • The new method offers significant advantages in terms of selectivity, mild conditions, and environmental impact for organic synthesis.