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Related Concept Videos

Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

9.6K
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
9.6K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

9.7K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
9.7K
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

6.3K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
6.3K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.5K
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...
8.5K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.0K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.0K
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

Nomenclature of Aromatic Compounds with Multiple Substituents

8.2K
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
8.2K

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Related Experiment Video

Updated: Aug 23, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

8.0K

[Sulfonyl-bis-(bromo-methyl-ene)]di-benzene.

Peter W R Corfield1

  • 1Department of Chemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA.

Iucrdata
|November 7, 2022
PubMed
Summary

The stereochemistry of a dibrominated organic compound was determined using X-ray crystallography. This revealed a 1,3-elimination reaction mechanism involving inversion of configuration at chiral centers.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Stereochemistry

Background:

  • The title compound, C14H12Br2O2S, is a diastereoisomer.
  • Understanding the stereochemical outcome of reactions is crucial in organic synthesis.

Purpose of the Study:

  • To determine the crystal structure of the title compound.
  • To elucidate the mechanism of 1,3-elimination of bromine using triphenylphosphine.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structure.
  • Analysis of the crystal structure provided insights into the reaction mechanism.

Main Results:

  • The compound crystallizes as the meso isomer of a diastereoisomeric pair.
Keywords:
1,3 eliminationcrystal structurediasteromersulfone

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  • The 1,3-elimination of bromine by triphenylphosphine proceeds with inversion of configuration at both chiral carbon atoms.

    • Conclusions:

    • The crystal structure determination was essential for understanding the stereochemical course of the elimination reaction.
    • Weak intermolecular interactions, including C-H⋯O and C-H⋯Br hydrogen bonds, stabilize the crystal structure.