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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

4.3K
Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
4.3K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

3.8K
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...
3.8K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

10.4K
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...
10.4K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

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The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
8.5K
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

7.9K
Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the final...
7.9K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

3.4K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Updated: Jan 3, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants
06:54

Elucidating the Metabolism of 2,4-Dibromophenol in Plants

Published on: February 10, 2023

1.5K

2,4-Dichloro-benzaldehyde.

Ricardo Cabello1, Maksymilian Chruszcz, Wladek Minor

  • 1University of Virginia, Department of Molecular Physiology & Biological Physics, 1340 Jefferson Park Avenue, Charlottesville, VA 22908, USA.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary
This summary is machine-generated.

The crystal structure of dichlorobenzaldehyde reveals molecules forming layered networks through C-H⋯O and π-π stacking interactions. These interactions stabilize the crystal lattice, influencing molecular arrangement.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding intermolecular forces is crucial for predicting crystal packing and material properties.
  • The role of weak interactions, such as C-H⋯O bonds and π-π stacking, significantly influences crystal lattice formation.
  • Dichlorobenzaldehyde serves as a model compound for studying these interactions in organic solids.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(7)H(4)Cl(2)O.
  • To identify and analyze the intermolecular interactions governing the molecular assembly in the solid state.
  • To quantify the degree of planarity or deviation from planarity of the aldehyde group relative to the benzene ring.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
  • Analysis of the crystal structure involved identifying hydrogen bonds (C-H⋯O) and π-π stacking interactions.
  • Geometric parameters, including bond lengths, bond angles, and torsion angles, were precisely measured.

Main Results:

  • The crystal structure reveals molecules arranged in layered networks.
  • Weak C-H⋯O interactions involving the aldehyde oxygen and ortho-hydrogen atoms, as well as formyl group interactions, were identified.
  • The layers are further stabilized by π-π stacking interactions between benzene rings with a centroid-centroid distance of 3.772(1) Å.
  • The aldehyde group exhibits a twist of 7.94(13)° relative to the benzene ring.

Conclusions:

  • The crystal packing of C(7)H(4)Cl(2)O is primarily dictated by a combination of C-H⋯O interactions and π-π stacking.
  • These supramolecular interactions lead to the formation of stable (10) layers, highlighting the importance of weak forces in crystal engineering.
  • The observed twist angle provides insight into the conformational preferences of the molecule in the solid state.