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

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

3.4K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
3.4K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

11.3K
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.
11.3K
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 Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.0K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
10.0K
Ionic Bonding and Electron Transfer02:48

Ionic Bonding and Electron Transfer

48.7K
Ions are atoms or molecules bearing an electrical charge. A cation (a positive ion) forms when a neutral atom loses one or more electrons from its valence shell, and an anion (a negative ion) forms when a neutral atom gains one or more electrons in its valence shell. Compounds composed of ions are called ionic compounds (or salts), and their constituent ions are held together by ionic bonds: electrostatic forces of attraction between oppositely charged cations and anions. 
48.7K
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

7.7K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
7.7K

You might also read

Related Articles

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

Sort by
Same author

Beyond the Fixed Charge: A New On-Tissue Derivatisation Strategy Employing Photoionisable Chromophores for Mass Spectrometry Imaging of Amino-Containing Metabolites.

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

Kinetic Analysis of Transmetalation at Prototypical Nickel<sup>(II)</sup> Catalyst Species: Rates, Mechanisms, and Implications for Catalysis.

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

Palladium(II)-catalysed intramolecular hydroamination of 3-alkynyltetrahydroquinolines to methanobenzo[<i>b</i>]azepines.

Chemical communications (Cambridge, England)·2025
Same author

Cascade Reactions of Indigo with an Allenylic Reactant.

Molecules (Basel, Switzerland)·2025
Same author

Synthesis and Reactivity of Atropo-Diastereomeric Benzoazepine-Fused Isoindoles.

The Journal of organic chemistry·2025
Same author

Dual metal organic framework post-synthetic modification; two birds with one stone.

Chemical communications (Cambridge, England)·2024

Related Experiment Video

Updated: Jan 17, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

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

Published on: March 24, 2018

69.6K

Developing an Ionic Halide Transfer and Addition Process Driven by Theoretical and Experimental Synergy.

Marzieh Bahmani1, Kimia Rahmannia1, Christopher Richardson1

  • 1School of Science, Molecular Horizons Research Institute, University of Wollongong, Wollongong, New South Wales 2500, Australia.

The Journal of Organic Chemistry
|September 20, 2025
PubMed
Summary

A new halide transfer and addition (HTA) reaction offers an ionic alternative to atom transfer radical addition (ATRA). This base-mediated method forms new carbon-carbon and carbon-halogen bonds from simple precursors.

More Related Videos

The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
12:43

The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique

Published on: November 28, 2016

9.1K
Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

9.9K

Related Experiment Videos

Last Updated: Jan 17, 2026

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

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

Published on: March 24, 2018

69.6K
The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
12:43

The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique

Published on: November 28, 2016

9.1K
Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

9.9K

Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Computational Chemistry

Background:

  • Atom Transfer Radical Addition (ATRA) is a widely used method for forming C-C bonds.
  • Developing novel, efficient, and versatile synthetic methods is crucial for organic chemistry.
  • Ionic reaction mechanisms offer alternative pathways to radical-based transformations.

Purpose of the Study:

  • To develop a novel ionic reaction as an alternative to the ATRA reaction.
  • To establish a base-mediated protocol for concurrent C(sp3)-C(sp3) and C(sp3)-X bond formation.
  • To elucidate the mechanism of the novel reaction using theoretical and experimental approaches.

Main Methods:

  • Combines theoretical (DFT modeling) and experimental approaches.
  • Utilizes a base-mediated protocol termed Halide Transfer and Addition (HTA).
  • Employs α-halo carbonyls and electron-deficient alkenes as starting materials.

Main Results:

  • Developed a novel ionic alternative to ATRA, named Halide Transfer and Addition (HTA).
  • Demonstrated concurrent formation of C(sp3)-C(sp3) and C(sp3)-X bonds.
  • DFT modeling revealed the role of 1,4-dioxane and K+ cation in reaction initiation and progression.

Conclusions:

  • The HTA reaction provides a new, efficient route for C-C and C-X bond formation.
  • The reaction mechanism involves a halogenophilic nucleophilic substitution (SN2X) pathway.
  • Synergistic optimization of the reaction model and mechanism was achieved through iterative experimental and theoretical studies.