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

Leaving Groups02:14

Leaving Groups

9.8K
The nature of leaving groups strongly influences the outcome of a nucleophilic substitution reaction.
In general, in a nucleophilic substitution reaction, a nucleophile displaces a functional group, called the leaving group, from the substrate to give a substituted product. A leaving group departs the substrate molecule through heterolytic cleavage, taking the pair of electrons with it to become a relatively stable weak base in the form of an anion or a neutral molecule.  
In a...
9.8K
Halogenation of Alkenes02:46

Halogenation of Alkenes

19.6K
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.
19.6K
Alkyl Halides02:45

Alkyl Halides

20.3K
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...
20.3K
Elimination Reactions02:25

Elimination Reactions

17.4K
A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...
17.4K
Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

14.9K
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products.
The following factors can influence the mechanisms competing against each other:
14.9K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.5K
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 stereochemistry.
9.5K

You might also read

Related Articles

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

Sort by
Same author

Copper-mediated oxidative deconstruction of polyethylene terephthalate <i>via</i> photoinduced ligand-to-metal charge transfer.

Organic & biomolecular chemistry·2026
Same author

"Pulling-Out" N<sub>2</sub> from Diazo Compounds by Iron Complex for Carbene Formation.

Inorganic chemistry·2026
Same author

NRG1-ErbB4 signaling in the mPFC mediates adolescent social isolation-induced depressive-like behaviors.

Pharmacological research·2026
Same author

Botulinum Toxin Type A Alleviates Hypertrophic Scar Formation in a Rabbit Ear Model by Inhibiting the TGF-β1/Smad Pathway.

Aesthetic plastic surgery·2026
Same author

Lithium-Germanium Alloy Interfaces for Efficient Low-Pressure Ammonia Synthesis.

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

The multilevel exploration test, a novel paradigm to measure exploratory behavior in depression animal models and the involvement of the PL-ZI circuit.

Acta pharmacologica Sinica·2026
Same journal

Enhanced and selective oxygen reduction by iron porphyrin with a biguanide residue in the second coordination sphere.

Chemical science·2026
Same journal

Excited-state orbital angular momentum enables all-optical molecular spin coherence.

Chemical science·2026
Same journal

Polyvinyl-based hole-transporting materials processed with non-destructive and green solvents for tin-lead perovskite solar cells and all-perovskite tandems.

Chemical science·2026
Same journal

Pd-catalyzed regio- and enantioselective allylation of cyclic allylboronates.

Chemical science·2026
Same journal

Covalent polyoxometalate-polyimide hybridization: multi-scale molecular engineering toward high-performance sodium-ion battery anodes.

Chemical science·2026
Same journal

Catalytic visible light-driven alkane dehydrogenation by a di-uranyl germanotungstate.

Chemical science·2026
See all related articles

Related Experiment Video

Updated: Feb 19, 2026

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

Modulating halide leaving-group trends through recognition by bisboranes.

Tong-Tong Liu1, Xiao-Wen Li1, Yun-Shu Cui1

  • 1Department of Chemistry, Fudan University Shanghai 200438 P. R. China zjshi@fudan.edu.cn zhaidandan@fudan.edu.cn liufeng@fudan.edu.cn.

Chemical Science
|February 18, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed a dynamic anion recognition system using a bidentate Lewis acid platform. This breakthrough enables a reversal of the typical halide leaving-group tendency in nucleophilic substitution reactions.

More Related Videos

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

69.7K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

8.4K

Related Experiment Videos

Last Updated: Feb 19, 2026

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
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

69.7K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

8.4K

Area of Science:

  • Synthetic Chemistry
  • Supramolecular Chemistry
  • Organometallic Chemistry

Background:

  • Modulating halide leaving-group ability is crucial but challenging in synthesis.
  • Existing methods lack control over the intrinsic reactivity of halides.

Purpose of the Study:

  • To develop a dynamic anion recognition system for halides.
  • To apply this system in nucleophilic substitution reactions.
  • To achieve an apparent reversal of the halide leaving-group tendency.

Main Methods:

  • Design and synthesis of a bidentate Lewis acid host.
  • Characterization of host-guest complexes using NMR spectroscopy and X-ray crystallography.
  • Competitive binding and anion exchange experiments.

Main Results:

  • Selective binding of halide ions by the Lewis acid platform.
  • Tunable binding affinities influenced by host cavity size.
  • Demonstrated reversal of bromide and chloride leaving abilities in catalyzed reactions.

Conclusions:

  • Dynamic anion recognition offers a novel strategy for controlling halide reactivity.
  • The developed system successfully reverses the conventional leaving-group sequence.
  • This approach opens new avenues in synthetic chemistry for organohalide transformations.