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 Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

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.
Alkyl Halides02:45

Alkyl Halides

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...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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.
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...

You might also read

Related Articles

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

Sort by
Same author

Nanoconfined CsPbBr<sub>3</sub> in Boron-Doped Mesoporous TiO<sub>2</sub> Enables Built-In Electric Field Modulation for Fully Selective CO<sub>2</sub>-to-CO Photoconversion.

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

From mineral to sensing: Colorimetric determination of ciprofloxacin from water and food samples using natural chalcopyrite as nanozyme.

Food chemistry·2025
Same author

Understanding Metal-Organic Framework Densification: Solvent Effects and the Growth of Colloidal Primary Nanoparticles in Monolithic ZIF-8.

Small (Weinheim an der Bergstrasse, Germany)·2025
Same author

Luminescent Alkylaluminium Anthranilates Reaching Unity Quantum Yield in the Condensed Phase.

Angewandte Chemie (International ed. in English)·2025
Same author

Water sorption studies with mesoporous multivariate monoliths based on UiO-66.

Materials advances·2024
Same author

Condensed Matter Systems Exposed to Radiation: Multiscale Theory, Simulations, and Experiment.

Chemical reviews·2024

Related Experiment Video

Updated: Jul 4, 2026

The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique
12:43

The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique

Published on: November 28, 2016

Hydride encapsulation by molecular alkali-metal clusters.

Joanna Haywood1, Andrew E H Wheatley

  • 1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK.

Dalton Transactions (Cambridge, England : 2003)
|June 27, 2008
PubMed
Summary

Researchers have developed a new method to synthesize main-group metal clusters using Lewis acids and organolithium reagents. This approach traps hydride ions within the cluster core, creating novel molecular structures.

More Related Videos

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
12:05

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia

Published on: October 10, 2013

Related Experiment Videos

Last Updated: Jul 4, 2026

The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique
12:43

The Synthesis of [Sn10(Si(SiMe3)3)4]2- Using a Metastable Sn(I) Halide Solution Synthesized via a Co-condensation Technique

Published on: November 28, 2016

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
12:05

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia

Published on: October 10, 2013

Area of Science:

  • Main-group chemistry
  • Organometallic chemistry
  • Coordination chemistry

Background:

  • Lewis acids react with organometallics to form 'ate' complexes.
  • An alternative pathway involves Lewis acid-mediated hydride abstraction via beta-elimination.

Purpose of the Study:

  • To explore the synthesis of novel molecular main-group metal clusters.
  • To understand the role of Lewis acids, organolithium reagents, and ligands in cluster formation.
  • To investigate the trapping of hydride ions within cluster cores.

Main Methods:

  • Reaction of group 12 and 13 Lewis acids with alkali-metal organometallics in the presence of N,N'-bidentate ligands.
  • Characterization of resulting molecular clusters, including structural analysis.
  • Exploration of synthetic variations to control cluster geometry and composition.

Main Results:

  • Successful synthesis of molecular main-group metal clusters featuring trapped interstitial hydride ions.
  • Demonstration that N,N'-bidentate ligands facilitate the trapping of LiH.
  • Identification of various cluster structures and exploration of methods to tune their properties.

Conclusions:

  • A novel synthetic route to hydride-encapsulating main-group metal clusters has been established.
  • The reaction pathway involving hydride abstraction and trapping offers new opportunities in main-group cluster chemistry.
  • Further research aims to control cluster formation catalytically and expand the scope of hydride-encapsulation.