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Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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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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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.
The hydrogenation process takes place on the...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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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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.
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Radical Formation: Abstraction00:47

Radical Formation: Abstraction

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The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Hydrogen-Abstraction/Acetylene-Addition Exposed.

Tao Yang1, Tyler P Troy2, Bo Xu2

  • 1Department of Chemistry, University of Hawai'i at Manoa, Honolulu, HI, 96822, USA.

Angewandte Chemie (International Ed. in English)
|October 27, 2016
PubMed
Summary
This summary is machine-generated.

The hydrogen-abstraction/acetylene-addition (HACA) mechanism

Keywords:
combustiongas-phase chemistryhydrogen-abstraction/acetylene-addition (HACA)mass spectrometrypolycyclic aromatic hydrocarbons

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Area of Science:

  • Combustion Chemistry
  • Astrochemistry
  • Physical Chemistry

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are prevalent in interstellar environments and meteorites.
  • The formation pathways of simple PAHs like naphthalene via the HACA mechanism are not fully understood.

Purpose of the Study:

  • To investigate the fundamental chemistry of styrenyl and ortho-vinylphenyl radicals with acetylene.
  • To provide experimental evidence for the HACA mechanism in naphthalene formation.

Main Methods:

  • Simulated combustion experiments.
  • Analysis of transient radical species and reaction products.

Main Results:

  • Experimental validation of the HACA mechanism for naphthalene formation from specific radicals.
  • Demonstrated facile formation of naphthalene under simulated combustion conditions.

Conclusions:

  • The HACA mechanism is crucial for naphthalene formation, bridging combustion and astrochemistry.
  • This study clarifies key reaction routes for the simplest polycyclic aromatic hydrocarbon.