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Related Concept Videos

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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.
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Reduction of Alkenes: Catalytic Hydrogenation02:13

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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.
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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

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Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

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The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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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.
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Hydrodealkenylative C(sp3)-C(sp2) Bond Fragmentation Using Isayama-Mukaiyama Peroxidation.

Jeremy H Dworkin1, Zhuoxi M Chen1, Kathleen C Cheasty1

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.

Journal of the American Chemical Society
|April 15, 2025
PubMed
Summary

This study introduces Isayama-Mukaiyama peroxidation (IMP) to overcome limitations of ozonolysis in dealkenylative synthesis. IMP enables functionalization of previously inaccessible alkene substrates, expanding synthetic possibilities.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Dealkenylative synthesis offers access to diverse products from alkenes.
  • Current methods rely on ozonolysis, which has significant substrate limitations.

Purpose of the Study:

  • To address the limitations of ozonolysis in dealkenylative synthesis.
  • To broaden the scope of alkene substrates amenable to dealkenylative functionalization.

Main Methods:

  • Utilized Isayama-Mukaiyama peroxidation (IMP) as an alternative to ozonolysis.
  • Developed novel radical hydrogenation conditions using catalytic [FeIII], benzenethiol, and γ-terpinene.

Main Results:

  • IMP successfully functionalized alkene substrates previously inaccessible via ozonolysis.
  • The novel radical hydrogenation resolved β-scission issues in IMP-generated peroxides.

Conclusions:

  • Isayama-Mukaiyama peroxidation expands the utility of dealkenylative synthesis.
  • This work provides a more versatile approach to alkene functionalization.