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Related Concept Videos

Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

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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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Radical Substitution: Allylic Bromination01:27

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Radical Reactivity: Overview01:11

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical Formation: Addition00:47

Radical Formation: Addition

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Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
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Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics01:32

Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics

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The anti-Markovnikov addition of hydrogen halides to an alkene is thermodynamically feasible only with HBr. The radical addition reaction with other hydrogen halides like HCl and HI is thermodynamically unfavorable.
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A Barrier-Free Atomic Radical-Molecule Reaction:  F + Propene.

Ji-Lai Li1, Cai-Yun Geng1, Xu-Ri Huang1

  • 1State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University, Changchun 130023, People's Republic of China.

Journal of Chemical Theory and Computation
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Atomic radical F reacts rapidly with propene via addition to the double bond or hydrogen abstraction. The study identifies the most feasible pathways, crucial for understanding halogen chemistry.

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Area of Science:

  • Chemical kinetics
  • Theoretical chemistry
  • Quantum chemistry

Background:

  • Understanding the reaction mechanisms of halogen radicals with alkenes is crucial for combustion and atmospheric chemistry.
  • Propene is a common alkene, and fluorine radical reactions are highly energetic.

Purpose of the Study:

  • To investigate the reaction mechanism of atomic radical F with propene.
  • To determine the most feasible reaction pathways and kinetics.
  • To provide insights into halogen chemistry.

Main Methods:

  • Detailed potential energy surface (PES) calculations using ab initio quantum chemistry methods (UMP2/6-311++G(d,p) and CCSD(T)/cc-pVTZ).
  • Application of transition-state theory.
  • Analysis of various reaction paths including addition-isomerization-elimination and H-atom abstraction.

Main Results:

  • The most feasible pathway involves F radical addition to the propene double bond, forming intermediates that rapidly dissociate.
  • Direct H-atom abstraction from the allylic position is also a highly feasible pathway.
  • Intermediates and transition states are energetically favorable, suggesting a rapid overall reaction.
  • No addition-elimination mechanism was found.

Conclusions:

  • The reaction between atomic radical F and propene is predicted to be rapid due to low-energy pathways.
  • Reaction channel competitiveness may depend on experimental conditions.
  • The findings aid in understanding halogen chemistry and reaction mechanisms.