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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
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Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

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The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
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Radical Substitution: Allylic Chlorination01:31

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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Halogen Radical Chemistry at Aqueous Interfaces.

Shinichi Enami1, Michael R Hoffmann2, A J Colussi2

  • 1National Institute for Environmental Studies , 16-2 Onogawa, Tsukuba, Ibaraki 305-8506, Japan.

The Journal of Physical Chemistry. A
|July 15, 2016
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Summary

Researchers identified new halogen activation pathways in marine environments. This study reveals how iodine radicals interact with bromide and iodide ions, forming key intermediates and products in atmospheric chemistry.

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Area of Science:

  • Atmospheric chemistry
  • Marine boundary layer science
  • Halogen chemistry

Background:

  • Halogens significantly influence atmospheric composition.
  • Interfacial halogen radical/halide reactions are crucial but poorly understood.
  • Limited in situ techniques hinder the study of fast interfacial reactions.

Purpose of the Study:

  • To investigate the mechanisms of interfacial halogen radical reactions.
  • To identify products and intermediates of reactions between iodine radicals and halide ions.
  • To develop new insights into atmospheric halogen activation pathways.

Main Methods:

  • Utilized online electrospray mass spectrometry.
  • Studied aqueous Br(-) and I(-) microjets.
  • Employed pulsed laser photolysis of CH3I to generate iodine radicals (I•).
  • Analyzed reactions in D2O and H2(18)O solutions.

Main Results:

  • Identified IBr(•)(-) and I2(•)(-) radical intermediates upon iodine radical uptake.
  • Observed rapid formation of trihalides (I2Br(-), IBr2(-), I3(-)) and I3On(-) species within microseconds.
  • Determined an effective uptake coefficient for iodine radicals on halide microjets (γeff ≥ 2 × 10(-4)).

Conclusions:

  • Elucidated key reaction mechanisms for halogen activation at interfaces.
  • Demonstrated a novel pathway for halogen activation initiated by photogenerated iodine radicals.
  • Highlighted the importance of interfacial reactions in atmospheric halogen cycling.