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Related Concept Videos

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.
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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.
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.
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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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

"Two functional groups in one package": using both alkyne π-bonds in cascade transformations.

Igor V Alabugin1, Brian Gold

  • 1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA. alabugin@chem.fsu.edu

The Journal of Organic Chemistry
|July 9, 2013
PubMed
Summary

Researchers leverage spatial orthogonality in alkynes for metal-free cascade reactions. This enables unique transformations like radical generation and alkyne disassembly without external initiators or light.

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Published on: August 16, 2018

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • Alkynes possess two independently addressable π-systems.
  • Spatial orthogonality offers unique reactivity pathways.
  • Metal-free transformations are highly desirable in green chemistry.

Purpose of the Study:

  • To explore the utility of spatial orthogonality in alkynes for metal-free cascade reactions.
  • To demonstrate novel reaction pathways enabled by this unique alkyne characteristic.
  • To showcase the versatility of alkynes in complex organic synthesis.

Main Methods:

  • Utilizing the spatial orthogonality of alkyne π-systems.
  • Designing and executing metal-free cascade reaction sequences.
  • Investigating reaction mechanisms including radical and ionic pathways.

Main Results:

  • Demonstrated metal-free cascade transformations.
  • Achieved generation of radicals without initiators.
  • Enabled light-free generation of excited states.
  • Showcased "1,2-dicarbene reactivity" in boomerang radical processes.
  • Facilitated selective alkyne conversion to carbonyl compounds.
  • Achieved full disassembly of the alkyne moiety.

Conclusions:

  • Spatial alkyne orthogonality is a powerful tool for designing metal-free cascade reactions.
  • This approach unlocks novel reactivity, including radical and excited-state generation.
  • The methodology offers versatile pathways for organic synthesis and alkyne functionalization.