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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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8.4K
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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E1 Reaction: Stereochemistry and Regiochemistry02:43

E1 Reaction: Stereochemistry and Regiochemistry

9.4K
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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8.5K
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.
8.5K
Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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3.1K
Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Understanding shape selectivity effects of hydroisomerization using a reaction equilibrium model.

Shrinjay Sharma1, Marcello S Rigutto2, Erik Zuidema2

  • 1Engineering Thermodynamics, Process and Energy Department, Faculty of Mechanical Engineering, Delft University of Technology, Leeghwaterstraat 39, 2628CB Delft, The Netherlands.

The Journal of Chemical Physics
|June 4, 2024
PubMed
Summary
This summary is machine-generated.

Zeolites with specific structures selectively produce branched alkanes through hydroisomerization. This study analyzes shape selectivity effects at chemical equilibrium, crucial for optimizing hydrocarbon yields.

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Area of Science:

  • Catalysis
  • Materials Science
  • Chemical Engineering

Background:

  • Hydroisomerization of linear alkanes produces valuable branched isomers, especially for long-chain hydrocarbons.
  • Understanding shape selectivity in zeolites is key to optimizing branched hydrocarbon yields.
  • Chemical equilibrium plays a critical role in reversible hydroisomerization reactions.

Purpose of the Study:

  • To analyze the shape selectivity effects of various zeolites on alkane isomer hydroisomerization at chemical reaction equilibrium.
  • To investigate conditions for achieving optimal yields of branched hydrocarbons.
  • To understand the distribution of reaction products for long-chain alkanes.

Main Methods:

  • Utilized a faster alternative to reaction ensemble Monte Carlo by imposing gas-phase chemical equilibrium and phase equilibrium between gas and adsorbed phases.
  • Employed Henry's law at infinite dilution and mixture adsorption isotherm models to calculate adsorbed loadings.
  • Simulated chemical equilibrium distribution in the adsorbed phase.

Main Results:

  • Zeolites with cage or channel structures show significant differences in selectivity for alkane isomers.
  • Pressure has a minimal impact on gas-phase equilibrium for these reactions within typical experimental temperatures (400-700K).
  • The study provides insights into reaction product distribution for long-chain alkanes.

Conclusions:

  • Zeolite structure significantly influences shape selectivity in alkane hydroisomerization.
  • The employed computational method effectively mimics adsorbed phase chemical equilibrium.
  • This research lays the groundwork for optimizing zeolite catalysts for selective alkane isomer production.