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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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Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...

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Related Experiment Video

Updated: May 11, 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

d-Phenyl-glycinium bromide.

Mohanadoss Parthasarathy1, Kannan Arun Kumar, Rengasamy Gopalakrishnan

  • 1Crystal Research Laboratory, Department of Physics, Anna University, Chennai 600 025, India.

Acta Crystallographica. Section E, Structure Reports Online
|May 2, 2013
PubMed
Summary
This summary is machine-generated.

Phenylglycinium bromide crystals feature linked cations and anions. Hydrogen bonds form sheets parallel to the (001) plane in this crystal structure.

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Last Updated: May 11, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
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Published on: November 22, 2016

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09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Understanding crystal structures is fundamental to materials science.
  • Hydrogen bonding plays a critical role in molecular assembly and material properties.

Purpose of the Study:

  • To elucidate the crystal structure of phenylglycinium bromide.
  • To investigate the hydrogen bonding interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of intermolecular interactions, specifically hydrogen bonds, was performed.

Main Results:

  • The crystal structure of phenylglycinium bromide (C8H10NO2(+)·Br(-)) was determined.
  • Phenylglycinium cations and bromide anions are linked via N-H⋯Br, O-H⋯Br, and C-H⋯O hydrogen bonds.
  • These interactions result in the formation of extended sheets parallel to the (001) crystallographic plane.

Conclusions:

  • The hydrogen bonding network dictates the overall crystal packing.
  • The observed sheet structure provides insights into the solid-state behavior of phenylglycinium bromide.