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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.3K
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.
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Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

7.2K
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

3.5K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.9K

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.
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Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

14.4K
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.
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.3K
Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
2.3K

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Alkane Solvent-Derived Acylation Reaction Driven by Electric Fields.

Xiye Wang1, Boyuan Zhang2, Brandon Fowler1

  • 1Department of Chemistry, Columbia University, New York, New York 10027, United States.

Journal of the American Chemical Society
|May 25, 2023
PubMed
Summary
This summary is machine-generated.

This study demonstrates electric field control over alkyl hydroperoxide activation for amine acylation on gold surfaces. This novel method, using scanning tunneling microscopy, generates alkylamides via electric field-induced acylium equivalents.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Area of Science:

  • Surface chemistry
  • Organic synthesis
  • Nanotechnology

Background:

  • Alkyl hydroperoxides are common byproducts of hydrocarbon autoxidation.
  • Functionalization of gold surfaces is crucial for various applications.
  • Novel methods for amine acylation are continuously sought.

Purpose of the Study:

  • To report a novel method for activating alkyl hydroperoxides using electric fields.
  • To investigate the formation of alkylamides via surface intermolecular coupling.
  • To explore the influence of electric field magnitude on this reactivity.

Main Methods:

  • Utilizing a scanning tunneling microscope (STM) break-junction setup.
  • Employing alkyl hydroperoxide mixtures generated from hydrocarbon autoxidation.
  • Performing surface functionalization and analysis of reaction products.

Main Results:

  • Alkyl hydroperoxides were successfully activated by electric fields to acylate amines.
  • Intermolecular coupling on gold surfaces yielded normal alkylamides.
  • The reaction's responsiveness to bias magnitude indicated electric field influence.

Conclusions:

  • A new pathway for alkyl hydroperoxide activation and amine acylation has been discovered.
  • Electric field control offers a novel approach to surface functionalization.
  • This method provides a pathway to generate acylium equivalents under specific conditions.