Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Formation of Halohydrin from Alkenes

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.

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...

Halogenation of Alkenes

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-Butadiene

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.

Radical Substitution: Allylic Bromination

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...

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

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.

You might also read

Related Articles

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

Sort by

Same author

α-C(sp<sup>3</sup>)-H Acetalization of Cyclic and Aliphatic Ethers Mediated by <i>N</i>-Bromoamides.

Organic letters·2026

Same author

Atroposelective Bromination for the Synthesis of Chiral Biaryl Phosphines via Cross-Assembled Catalysis with Chiral Phosphoric Acid and Achiral Phenol.

Journal of the American Chemical Society·2026

Same author

Twenty Years of the Asian Core Program on Cutting-Edge Organic Chemistry in Asia (ACP-CEOCA): A Retrospective of the Last Decade.

Chemistry, an Asian journal·2026

Same author

Pillar[5]arene-catalyzed anti-Markovnikov halogenations through cationic intermediates stabilization in confined spaces.

Nature communications·2026

Same author

Co-Overexpression of Ankyrin Repeat Domain-Containing Protein 2A and Vacuolar H<sup>+</sup>-Pyrophosphatase Enhances Salt Tolerance through Auxin Homeostasis in Cotton.

Journal of agricultural and food chemistry·2026

Same author

Halide Bond Assisted Double Desymmetrization of Meso-Dicarboxylic Acids with Symmetrical Olefins via Asymmetric Halogenation.

Angewandte Chemie (International ed. in English)·2026

Search research articles

Related Experiment Video

Updated: Dec 15, 2025

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

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

Published on: May 26, 2019

Zwitterion-Catalyzed Intermolecular Bromoesterifications.

Wing-Hin Ng¹, Rong-Bin Hu¹, Ying-Pong Lam¹

¹Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China.

Organic Letters

|July 9, 2020

Summary

This study introduces a novel zwitterion catalyst for intermolecular bromoesterification, enabling the reaction of equimolar amounts of acid and olefin. This breakthrough overcomes the need for excess acid, enhancing efficiency in synthesizing valuable building blocks.

More Related Videos

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

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

Published on: March 20, 2014

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

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

Published on: February 24, 2015

Related Experiment Videos

Last Updated: Dec 15, 2025

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

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

Published on: May 26, 2019

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

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

Published on: March 20, 2014

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

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

Published on: February 24, 2015

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Intermolecular haloesterification yields valuable synthetic building blocks.
Traditional methods often require super-stoichiometric acid due to low reactant reactivity.

Purpose of the Study:

To develop a more efficient intermolecular bromoesterification protocol.
To enable the use of equimolar ratios of acid and olefin, reducing waste and improving atom economy.

Main Methods:

Zwitterion-catalyzed reaction.
Utilizing N-bromosuccinimide (NBS) as the bromine source.
Equimolar ratio of carboxylic acid and olefin.

Main Results:

Successful intermolecular bromoesterification achieved with equimolar acid and olefin.
Zwitterion catalyst demonstrated high efficiency.
Mechanistic studies elucidated the synergistic role of the zwitterion's charge pair in activating NBS and carboxylic acid.

Conclusions:

The developed zwitterion-catalyzed method offers an efficient alternative to traditional haloesterification.
This approach minimizes acid waste and enhances the synthesis of important organic intermediates.