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

Alkyl Halides02:45

Alkyl Halides

20.2K
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...
20.2K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

10.2K
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.
10.2K
Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

8.5K
This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
8.5K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

11.3K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
11.3K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

12.3K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
12.3K

You might also read

Related Articles

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

Sort by
Same author

Incorporation of Organic Counter-Cations Into Poly(Heptazine Imide) Networks for Promoting Proton-Coupled Electron Transfer During Photocatalytic H<sub>2</sub>O<sub>2</sub> Evolution.

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

Genome-Wide Analysis of AGPase Identifies <i>CsAGP4</i> as a Regulator of Watermelon Mosaic Virus Resistance in Cucumber.

International journal of molecular sciences·2026
Same author

A Multilayer Decision-Making Method for UAV Formation Cooperative Flight in Complex Urban Environments.

Sensors (Basel, Switzerland)·2026
Same author

Programmable Solid-Electrolyte Interfaces for Efficient and Selective Electrochemical Hydrogenations.

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

The effect of family continuity management on the anxiety level of parents of children with febrile seizures and recurrence rate.

Frontiers in medicine·2026
Same author

Correction: Microbiome-inspired solutions to save human and planetary health.

Frontiers in microbiology·2026

Related Experiment Video

Updated: Feb 16, 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

69.7K

Thioimidazolium Ionic Liquids as Tunable Alkylating Agents.

Ryan Guterman1, Han Miao1, Markus Antonietti1

  • 1Department of Colloid Chemistry, Max Planck Institute of Colloids and Interfaces Max Planck Institute for Colloids and Interfaces , Am Mühlenberg 1 OT-Golm, 14476 Potsdam, Germany.

The Journal of Organic Chemistry
|December 20, 2017
PubMed
Summary

New thioimidazolium-based ionic liquids act as effective alkylating agents. Their reactivity can be tuned by modifying the cation and anion, offering a versatile platform for designing novel alkylating compounds.

More Related Videos

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds
05:59

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds

Published on: September 27, 2024

2.5K
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

10.0K

Related Experiment Videos

Last Updated: Feb 16, 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

69.7K
Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds
05:59

Author Spotlight: Advancing Antimicrobial Resistance Research with Innovative Approaches and Synthetic Compounds

Published on: September 27, 2024

2.5K
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

10.0K

Area of Science:

  • Ionic liquid chemistry
  • Organic synthesis
  • Materials science

Background:

  • Ionic liquids (ILs) offer tunable properties like low melting points and nonvolatility.
  • Alkylating agents are crucial in organic synthesis but often face challenges with specificity and handling.
  • Thioimidazolium structures present a novel scaffold for combining IL properties with alkylating capabilities.

Purpose of the Study:

  • To develop and characterize novel alkylating ionic liquids (AILs) based on the thioimidazolium framework.
  • To investigate the influence of structural modifications (cation and anion) on AIL reactivity and alkylating efficiency.
  • To demonstrate the potential of AILs as a modular platform for designing tailored alkylating agents.

Main Methods:

  • Synthesis of various S-alkyl thioimidazolium salts with different cations and anions.
  • Evaluation of alkyl transfer efficiency and reactivity through controlled alkylation reactions.
  • Spectroscopic and electrochemical methods to characterize the AILs and understand reaction mechanisms.

Main Results:

  • Alkyl transfer occurs specifically from the S-alkyl position of the thioimidazolium cation.
  • Cation derivatization, particularly with a caffeine-derived moiety, significantly enhanced reactivity.
  • Anion choice impacts reaction rates, with iodide anions facilitating alkylation via a proposed "shuttling" mechanism.
  • The developed AILs exhibit tunable electrophilicity and reactivity.

Conclusions:

  • Thioimidazolium-based AILs provide a versatile and modular platform for alkylating agent design.
  • Structural tuning of both cation and anion allows for precise control over reactivity and performance.
  • These AILs hold promise for integration into various chemical processes requiring specific alkylation.