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Related Concept Videos

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

10.6K
Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
10.6K
Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

17.0K
Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
17.0K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

9.4K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
9.4K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

11.0K

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.
11.0K
Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

23.5K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
23.5K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.5K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
3.5K

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Updated: Jan 12, 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
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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

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Alkynes Hydration in Three-Component Double-Acidic Deep Eutectic Solvents.

Alessandra Gritti1,2, Valentina Pirovano1, Alessandro Caselli2

  • 1Department of Pharmaceutical Sciences, General and Organic Chemistry Section "A. Marchesini", University of Milan, via Golgi 19, 20133, Milano, Italy.

Chemsuschem
|November 3, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces a sustainable hydration method for alkynes using novel deep eutectic solvents (DESs) as triple-active media, yielding ketones with high Markovnikov regioselectivity.

Keywords:
alkynesdeep eutectic solventshydrationketonesmicrowaves

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Area of Science:

  • Green Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Hydration of alkynes is a fundamental organic transformation.
  • Traditional methods often involve harsh reagents or lack regioselectivity.
  • Development of sustainable and efficient alkyne hydration methods is crucial.

Purpose of the Study:

  • To present a novel, sustainable method for alkyne hydration.
  • To utilize novel triple-active deep eutectic solvents (DESs) as reaction media.
  • To achieve complete Markovnikov regioselectivity in ketone formation.

Main Methods:

  • Employing three-component, double-acidic deep eutectic solvents (DESs) as solvents, reagents, and catalysts.
  • Conducting the hydration reaction under conventional or dielectric heating.
  • Utilizing microwave heating for enhanced sustainability with terminal alkynes.

Main Results:

  • Successful hydration of both terminal and internal alkynes to form ketones.
  • Complete Markovnikov regioselectivity achieved in all tested reactions.
  • Good to excellent yields obtained for the desired ketone products.
  • Demonstrated reusability of the deep eutectic solvent reaction medium.

Conclusions:

  • The developed method offers a sustainable and efficient route for alkyne hydration.
  • Deep eutectic solvents (DESs) show promise as versatile triple-active media in organic synthesis.
  • The process aligns with green chemistry principles, evidenced by favorable green metrics (sE-factor and EcoScale).