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Related Concept Videos

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.
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
When dissolved in liquid ammonia, an alkali metal, such as sodium, dissociates into a...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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.

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Related Experiment Video

Updated: Jun 18, 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

Reduction of solid-supported olefins and alkynes.

David P Dickson1, Christine Toh, Menaka Lunda

  • 1University of Illinois at Chicago Department of Chemistry (MC 111) 845 West Taylor Street, Room 4500 SES, Chicago, Illinois 60607, USA.

The Journal of Organic Chemistry
|November 17, 2009
PubMed
Summary

This study explored the reduction of carbon-carbon multiple bonds using supported catalysts. Titanocene and copper hydride reagents effectively reduced alkynes and unsaturated ketones, respectively.

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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

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Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
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Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

Published on: April 2, 2018

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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

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
09:08

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

Published on: April 2, 2018

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Polymer-supported Synthesis

Background:

  • Carbon-carbon multiple bonds (alkynes and olefins) are key functional groups in organic synthesis.
  • Developing efficient and selective reduction methods is crucial for synthesizing complex molecules.
  • Polymer-supported reagents offer advantages in catalyst recovery and purification.

Purpose of the Study:

  • To investigate the reduction of carbon-carbon multiple bonds in alkynes and olefins using polymer-supported reagents.
  • To evaluate the efficacy of titanocene and copper(I) hydride reagents for specific reduction reactions.

Main Methods:

  • Utilized a polystyrene resin as a support for catalytic reagents.
  • Employed homogeneous titanocene catalysis for the reduction of diarylacetylenes.
  • Applied copper(I) hydride reagents for the reduction of alpha,beta-unsaturated ketones.

Main Results:

  • Titanocene reagents achieved stereoselective synthesis of cis-olefins from diarylacetylenes.
  • Copper(I) hydride reagents demonstrated effectiveness in reducing alpha,beta-unsaturated ketones.
  • The use of a polystyrene support facilitated catalyst handling.

Conclusions:

  • Polymer-supported titanocene and copper(I) hydride reagents are effective for selective reductions.
  • This approach offers a practical method for synthesizing cis-olefins and reducing unsaturated ketones.
  • Supported catalysis provides a viable strategy for greener chemical synthesis.