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Structure and Nomenclature of Ethers

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...

Nomenclature of Aromatic Compounds with a Single Substituent

Nomenclature of Aromatic Compounds with a Single Substituent

Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.

NMR Spectroscopy of Benzene Derivatives

NMR Spectroscopy of Benzene Derivatives

Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...

Nomenclature of Aromatic Compounds with Multiple Substituents

Nomenclature of Aromatic Compounds with Multiple Substituents

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...

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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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Related Experiment Video

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Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

erythro-{1-Bromo-1-[(1-phenyl-eth-yl)sulfon-yl]eth-yl}benzene.

Peter W R Corfield¹

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

|April 8, 2024

Summary

This study reveals that 1,3 elimination reactions of specific sulfone isomers proceed with inversion at each chiral center, yielding substituted stilbenes. Molecular structure analysis confirmed this stereochemical outcome and identified crystal network interactions.

Keywords:

1,3-elimination C—H⋯O and C—H⋯Br hydrogen bonding crystal structure diasteromer sulfone

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Area of Science:

Organic Chemistry
Crystallography
Stereochemistry

Background:

Sulfones are versatile organic compounds with diverse applications.
Diastereomeric sulfones present unique stereochemical challenges.
Understanding reaction mechanisms is crucial for synthetic control.

Purpose of the Study:

To elucidate the stereochemical outcome of 1,3 elimination reactions in diastereomeric sulfones.
To determine the crystal structure of the title compound (C16H17BrO2S).
To investigate intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction for structural analysis.
Stereochemical analysis of reaction products.
Identification of hydrogen bonding networks.

Main Results:

The title compound crystallizes as the erythro (RR/SS) isomer.
1,3 elimination reactions occur with inversion at each asymmetric carbon atom.
C-H⋯Br and C-H⋯O hydrogen bonds form a tri-periodic network.

Conclusions:

The stereochemistry of the 1,3 elimination reaction is confirmed to involve inversion.
The crystal structure provides insights into intermolecular forces in sulfone derivatives.
This research contributes to the understanding of stereoselective synthesis and crystal engineering.