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

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

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 bromine molecule...
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Radical Substitution: Allylic Bromination

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 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.
Acid Halides to Alcohols: LiAlH4 Reduction01:19

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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
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Related Experiment Video

Updated: Jun 13, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Reductive dissolution of lead dioxide (PbO2) in acidic bromide solution.

Yi-Pin Lin1, Richard L Valentine

  • 1Division of Environmental Science and Engineering, Faculty of Engineering, National University of Singapore, Singapore 117576. eselinyp@nus.edu.sg

Environmental Science & Technology
|April 28, 2010
PubMed
Summary

Reductive dissolution of lead dioxide (PbO(2)(s)) in drinking water is clarified. Bromide and acid accelerate PbO(2)(s) dissolution through surface reactions and electron transfer, impacting lead levels.

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Published on: December 29, 2016

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Last Updated: Jun 13, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
08:46

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Published on: November 22, 2016

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)
10:42

Combining Solid-state and Solution-based Techniques: Synthesis and Reactivity of Chalcogenidoplumbates(II or IV)

Published on: December 29, 2016

Area of Science:

  • Environmental Chemistry
  • Surface Chemistry
  • Geochemistry

Background:

  • Reductive dissolution of lead dioxide (PbO(2)(s)) is a key pathway for elevated lead in drinking water.
  • Surface processes governing this heterogeneous reaction remain poorly understood.

Purpose of the Study:

  • To investigate the kinetics and mechanism of PbO(2)(s) reductive dissolution in acidic bromide solutions.
  • To elucidate the detailed surface reactions involved in lead release.

Main Methods:

  • Kinetic experiments were conducted in acidic bromide solutions.
  • Reaction orders with respect to bromide and proton concentrations were determined.
  • A surface reaction mechanism was proposed and validated against kinetic data.

Main Results:

  • The reaction rate is proportional to PbO(2)(s) concentration.
  • Reaction orders were determined as 1.08 for bromide and 1.77 for protons.
  • A mechanism involving bromide adsorption, surface complex formation, and two one-electron transfers was elucidated.

Conclusions:

  • Bromide adsorption and the first one-electron transfer are rate-limiting steps.
  • The proposed surface reaction mechanism explains the observed kinetics.
  • Similar mechanisms may apply to other reductive ions impacting metal oxides.