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

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

You might also read

Related Articles

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

Sort by

Same author

One-Pot Synthesis of Novel 3-{(1H-Benzo[d]Imidazol-2-yl)Amino(Phenyl)Methyl}Benzofuran-2(3H)-Ones as Antimicrobial Agents and Their Molecular Docking Studies.

Archiv der Pharmazie·2025

Same author

New frontiers in multicomponent mechanosynthesis for organic molecules: modern marvels.

Molecular diversity·2024

Same author

Impact of an aryl bulky group on a one-pot reaction of aldehyde with malononitrile and <i>N</i>-substituted 2-cyanoacetamide.

RSC advances·2022

Same author

Synthesis and in vitro study of antiproliferative benzyloxy dihydropyrimidinones.

Archiv der Pharmazie·2021

Search research articles

Related Experiment Video

Updated: Jun 11, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Recent trends for chemoselectivity modulation in one-pot organic transformations.

Hiren R Chaudhary¹, Divyang M Patel¹

¹Department of Chemistry, Sankalchand Patel University Visnagar 384315 Gujarat India divyangpatel.dm@gmail.com dmpatel.fsh@spu.ac.in.

|October 1, 2024

Summary

Chemoselectivity in organic synthesis enables selective reactions. This review explores one-pot methods for novel molecule synthesis, highlighting key factors like substrate and temperature for controlling chemoselectivity.

More Related Videos

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Published on: January 4, 2018

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Related Experiment Videos

Last Updated: Jun 11, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Published on: January 4, 2018

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Chemoselectivity is crucial for organic reactions, involving selective reactivity of one functional group over others.
One-pot reactions are efficient for synthesizing diverse heterocyclic and carbocyclic compounds.

Purpose of the Study:

To review recent advancements (2013-2024) in synthesizing novel organic molecules using chemoselective one-pot reactions.
To provide insights into the mechanisms of these synthetic methodologies.

Main Methods:

Literature review of chemoselective one-pot reactions.
Analysis of factors influencing chemoselectivity: substrate, catalyst, solvent, and temperature.
Examination of reported synthetic strategies for novel heterocycles and carbocycles.

Main Results:

Compilation of diverse chemoselective one-pot synthetic strategies.
Identification of critical reaction parameters affecting chemoselectivity.
Demonstration of successful synthesis of novel heterocyclic and carbocyclic compounds.

Conclusions:

Chemoselective one-pot reactions offer powerful strategies for novel organic molecule synthesis.
Careful selection of reagents and reaction conditions is key to achieving high chemoselectivity.
This approach holds significant potential for discovering new heterocycles and carbocycles.