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Related Concept Videos

Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

3.3K
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
3.3K
E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

10.2K
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
10.2K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

9.4K
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.
9.4K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.7K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.7K
E1 Reaction: Kinetics and Mechanism02:46

E1 Reaction: Kinetics and Mechanism

14.5K
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of the leaving group and abstraction of the beta hydrogen by a weak base. Typically, the experimental proof for the E1 mechanism is via kinetic studies or isotope studies. While the former demonstrates the first-order kinetics—the dependence of the reaction solely on substrate concentration—the latter proves the abstraction of hydrogen only...
14.5K
Ethers to Alkyl Halides: Acidic Cleavage02:18

Ethers to Alkyl Halides: Acidic Cleavage

5.2K
Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, poor leaving groups. However, ethers readily undergo acidic-cleavage reactions. Ethers can be converted to alkyl halides when heated with strong acids such as HBr and HI in a sequence of two substitution reactions.
5.2K

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Effects of functional group interactions on the bimolecular and dissociation reactions of diols.

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Determination of orders of relative alkali metal ion affinities of crown ethers and acyclic analogs by the kinetic method.

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Related Experiment Video

Updated: May 5, 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

71.2K

Gas-phase complexation of polyethers with halide ions.

C C Liou1, J S Brodbelt

  • 1Department of Chemistry, University of Texas, 78712-1167, Austin, TX, USA.

Journal of the American Society for Mass Spectrometry
|November 16, 2013
PubMed
Summary

Crown ethers and acyclic analogs complex with halide anions. Fluoride complexes show unique dissociation, indicating high basicity and intramolecular proton abstraction, unlike other halides.

Area of Science:

  • Physical Chemistry
  • Mass Spectrometry
  • Supramolecular Chemistry

Background:

  • Crown ethers and their acyclic analogs are versatile hosts for various guest molecules.
  • Halide anions are important in chemical and biological systems.
  • Understanding anion-host interactions is crucial for developing new chemical sensors and separation technologies.

Purpose of the Study:

  • To investigate the gas-phase interactions between halide anions (F-, Cl-, Br-, I-) and crown ethers/acyclic analogs.
  • To elucidate the dissociation mechanisms of these complexes under collisional activation.
  • To determine the relative binding affinities of halide anions to different host molecules.

Main Methods:

  • Ion-molecule reactions were employed in the chemical ionization source of a triple-quadrupole mass spectrometer.

More Related Videos

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

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Last Updated: May 5, 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

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

7.3K
  • Collisional activation was used to induce dissociation of the formed halide-ether complexes.
  • The kinetic method was applied to establish relative halide binding strengths.

    • Main Results:

    • Iodide, bromide, and chloride complexes dissociated via cleavage of electrostatic hydrogen bonds, releasing bare halide anions.
    • Fluoride complexes exhibited unique dissociation pathways, including loss of HF and ethylene oxide units, suggesting intramolecular proton abstraction.
    • Relative binding affinities were established, with a notable trend for chloride and bromide affinities across various crown ethers and acyclic analogs.

    Conclusions:

    • Fluoride ion displays distinct gas-phase complexation and dissociation behavior compared to other halides due to its higher basicity.
    • The observed dissociation mechanism for fluoride complexes highlights its ability to promote intramolecular reactions within the host molecule.
    • The study provides valuable data on halide-host interactions, contributing to the understanding of supramolecular chemistry and ion binding.