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Related Concept Videos

Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

13.2K
In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.7K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
11.7K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

11.1K
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.
11.1K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
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.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.7K
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...
6.7K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.8K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
3.8K

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A Facile Synthetic Method to Obtain Bismuth Oxyiodide Microspheres Highly Functional for the Photocatalytic Processes of Water Depuration
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A surface-stabilized ozonide triggers bromide oxidation at the aqueous solution-vapour interface.

Luca Artiglia1,2, Jacinta Edebeli1,3, Fabrizio Orlando1

  • 1Laboratory of Environmental Chemistry, Paul Scherrer Institut, 5232, Villigen, Switzerland.

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Researchers found evidence of an ozonide intermediate in bromide oxidation by ozone, which is crucial for atmospheric chemistry. This ozonide prefers the air-water interface, impacting tropospheric ozone budgets.

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Area of Science:

  • Environmental Chemistry
  • Atmospheric Chemistry
  • Physical Chemistry

Background:

  • Bromide oxidation by ozone is vital for tropospheric ozone budget.
  • The reaction mechanism in aqueous environments is not fully understood.
  • Heterogeneous oxidation at the air-water interface is suspected to be significant.

Purpose of the Study:

  • To provide direct experimental evidence for the ozonide intermediate in bromide oxidation by ozone.
  • To investigate the role of the solution-vapour interface in this reaction.
  • To elucidate the reaction kinetics and mechanisms at the interface versus the bulk aqueous phase.

Main Methods:

  • Liquid jet X-ray photoelectron spectroscopy (XPS) for direct detection.
  • Theoretical calculations to support experimental findings.
  • Kinetic experiments to determine reaction rates.

Main Results:

  • Direct experimental evidence for the ozonide intermediate ([Br•OOO-]) was obtained.
  • The ozonide was found to preferentially accumulate at the solution-vapour interface.
  • Water stabilizes the ozonide and lowers the transition state energy at neutral pH.
  • Heterogeneous oxidation pathway dominates at low, atmospherically relevant ozone concentrations.

Conclusions:

  • The ozonide is a surface-active species, accelerating heterogeneous oxidation of bromide.
  • Reaction kinetics and mechanisms differ significantly between the aqueous bulk and the air-water interface.
  • This finding has implications for understanding atmospheric chemistry and ozone budgets.