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Related Concept Videos

Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Esters to Alcohols: Grignard Reaction01:08

Esters to Alcohols: Grignard Reaction

The reaction of an ester with a Grignard reagent, followed by hydrolysis of the magnesium alkoxide salt in aqueous acid, yields a tertiary alcohol. In the case of formate esters, secondary alcohols are formed.
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
Nitriles to Ketones: Grignard Reaction00:57

Nitriles to Ketones: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard reagent...
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

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:

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Related Experiment Video

Updated: May 26, 2026

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

Solid-supported gallium triflate: an efficient catalyst for the three-component ketonic Strecker reaction.

Charlotte Wiles1, Paul Watts

  • 1Chemtrix BV, Burgemeester Lemmensstraat 358, 6163JT Geleen, The Netherlands. c.wiles@chemtrix.com

Chemsuschem
|December 14, 2011
PubMed
Summary

Researchers developed a solid-supported gallium triflate catalyst for improved efficiency and cost-effectiveness in chemical synthesis. This novel catalyst demonstrated higher yield and purity in the ketonic Strecker reaction compared to traditional methods.

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

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

Related Experiment Videos

Last Updated: May 26, 2026

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

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

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

Area of Science:

  • Catalysis
  • Organic Synthesis
  • Materials Science

Background:

  • Rare earth metal triflates are gaining attention as water-tolerant Lewis acid catalysts.
  • Developing cost-effective and cleaner catalytic processes is crucial for synthetic chemistry.
  • Solid-supported catalysis offers advantages in terms of separation and reusability.

Purpose of the Study:

  • To develop a solid-supported gallium triflate (PS-Ga(OTf)2) catalyst.
  • To enhance the cleanliness and cost-effectiveness of using rare earth metal triflates.
  • To evaluate the catalytic activity of PS-Ga(OTf)2 in the ketonic Strecker reaction.

Main Methods:

  • Synthesis of a solid-supported gallium triflate derivative (PS-Ga(OTf)2).
  • Screening the catalytic activity of PS-Ga(OTf)2 in the ketonic Strecker reaction.
  • Comparison of results with homogeneous gallium triflate catalysis.

Main Results:

  • The solid-supported gallium triflate (PS-Ga(OTf)2) was successfully synthesized.
  • PS-Ga(OTf)2 demonstrated high activity in the ketonic Strecker reaction.
  • The reaction using PS-Ga(OTf)2 yielded target α-aminonitriles in higher yield and purity compared to homogeneous catalysis.

Conclusions:

  • Solid-supported gallium triflate is an effective and advantageous catalyst for the ketonic Strecker reaction.
  • This approach offers improved yield, purity, cleanliness, and cost-effectiveness.
  • The study highlights the potential of combining solid-supported catalysis with micro-reaction technology.