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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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.
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

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Related Experiment Video

Updated: Jul 6, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Alkenol-alkyne cross metathesis.

Daniel A Clark1, Joseph R Clark, Steven T Diver

  • 1Department of Chemistry, University at Buffalo, The State University of New York, Amherst, New York 14260, USA.

Organic Letters
|April 16, 2008
PubMed
Summary

Hydroxy-functionalized dienes were synthesized using enyne cross metathesis of allyl alcohols. A method was developed to convert these into the desired (E)-diene products, overcoming isomerization issues during heating.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Enyne metathesis is a powerful tool for carbon-carbon bond formation.
  • Hydroxy-functionalized dienes are valuable synthetic intermediates.

Purpose of the Study:

  • To develop a method for synthesizing hydroxy-functionalized dienes via enyne cross metathesis.
  • To address and overcome isomerization issues encountered during the synthesis.

Main Methods:

  • Enyne cross metathesis reaction utilizing allyl alcohols and their homologues.
  • Optimization of reaction conditions to control isomerization.
  • Development of a post-reaction conversion strategy for (E)-diene formation.

Main Results:

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Last Updated: Jul 6, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Published on: December 16, 2019

  • Successful synthesis of hydroxy-functionalized dienes.
  • Identification of an isomerization pathway under prolonged heating.
  • Establishment of a reliable method for selective (E)-diene product formation.
  • Conclusions:

    • Enyne cross metathesis provides access to hydroxy-functionalized dienes.
    • Isomerization can be managed to favor the desired (E)-diene isomer.
    • The developed method offers a practical route to valuable diene products.