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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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...
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.
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

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Related Experiment Video

Updated: Jun 1, 2026

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
09:46

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

2,4-Difluoro-phenyl-boronic acid.

Patricia Rodríguez-Cuamatzi, Hugo Tlahuext, Herbert Höpfl

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study reveals the planar molecular structure of C(6)H(5)BF(2)O(2), showing electronic delocalization. Crystal analysis identified hydrogen bonds forming molecular sheets, highlighting the compound

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Understanding the electronic properties and intermolecular interactions of organoboron compounds is crucial.
    • Aromatic compounds with boron substituents offer unique chemical behaviors.

    Purpose of the Study:

    • To elucidate the molecular structure and electronic delocalization of C(6)H(5)BF(2)O(2).
    • To investigate the hydrogen bonding network and crystal packing in the solid state.

    Main Methods:

    • X-ray crystallography was employed to determine the precise atomic arrangement.
    • Analysis of bond lengths, angles, and deviations from planarity.

    Main Results:

    • The compound C(6)H(5)BF(2)O(2) exhibits an essentially planar molecular structure.

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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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    Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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    Published on: August 19, 2013

    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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    Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
    09:45

    Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

    Published on: April 27, 2017

  • Evidence of electronic delocalization between the dihydroxy-boryl group and the phenyl ring was observed.
  • Crystal structure analysis revealed inversion dimers linked by O-H⋯O hydrogen bonds.
  • An intramolecular O-H⋯F hydrogen bond stabilizes the conformation, with the hydrogen also participating in intermolecular O-H⋯F links, forming molecular sheets.

    • Conclusions:

    • The planar geometry and observed delocalization suggest significant electronic interaction within the molecule.
    • The hydrogen bonding network dictates the crystal packing, leading to the formation of extended molecular sheets.