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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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.
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Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

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An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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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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Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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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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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

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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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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

2.1K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Related Experiment Video

Updated: Apr 28, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Bromate oxidized from bromide during sonolytic ozonation.

Ning Lu1, Xue-Fei Wu2, Ji-Zhi Zhou2

  • 1Shanghai National Engineering Research Center of Urban Water Resources, Shanghai 200082, China; School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, China.

Ultrasonics Sonochemistry
|June 17, 2014
PubMed
Summary

Sonolytic ozonation (US/O3) enhances bromate formation from bromide in drinking water, particularly at lower ozone flows. Ultrasound significantly boosts bromate conversion, showing potential for rapid water treatment.

Keywords:
BromateDrinking waterOzonationSonolysis

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Area of Science:

  • Environmental Chemistry
  • Water Treatment Technologies
  • Advanced Oxidation Processes

Background:

  • Sonolytic ozonation (US/O3) improves pollutant degradation via enhanced mass transfer and hydroxyl radical formation.
  • Bromate (BrO3(-)) is a disinfection byproduct of concern in drinking water treatment.

Purpose of the Study:

  • To investigate the formation of bromate from bromide during sonolytic ozonation.
  • To elucidate the mechanisms influencing bromate formation under US/O3 conditions.

Main Methods:

  • Experimental investigation of bromate formation kinetics under varying sonolytic ozonation parameters.
  • Analysis of bromate conversion rates at different pH levels and ozone flow rates.
  • Assessment of radical species and byproduct formation under ultrasound.

Main Results:

  • Bromate conversion rate ([BrO3(-)]/[Br(-)]0) reached 60% at neutral pH with ultrasound and continuous ozone flow (0-0.2 Lmin(-1)).
  • Sonolysis significantly promoted bromate formation due to ozone decomposition and enhanced gas-liquid transfer.
  • Bromate formation increased with pH, but was inhibited at high ozone flow rates due to competition with bromide and hydrogen peroxide generation.

Conclusions:

  • Sonolytic ozonation effectively enhances bromate formation from bromide in drinking water treatment.
  • Optimizing ozone flow rate (<0.2 Lmin(-1)) is crucial for maximizing bromate formation under US/O3.
  • Understanding these mechanisms is vital for controlling disinfection byproduct formation in water treatment.