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Structure and Nomenclature of Epoxides

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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 groups, ethers can be classified into two...

Autoxidation of Ethers to Peroxides and Hydroperoxides

Autoxidation of Ethers to Peroxides and Hydroperoxides

Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.

Acidity and Basicity of Alcohols and Phenols

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.

Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...

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Related Experiment Video

Updated: May 27, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

(E)-4-Phenyl-butan-2-one oxime.

Hoong-Kun Fun, Wan-Sin Loh, Reshma Kayarmar

Acta Crystallographica. Section E, Structure Reports Online

|November 9, 2011

Summary

This summary is machine-generated.

This study details the molecular structure of a novel organic compound, C(10)H(13)NO. Researchers observed a specific torsion angle and identified intermolecular hydrogen bonds forming crystal dimers.

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Area of Science:

Organic Chemistry
Crystallography
Molecular Structure Analysis

Background:

Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
Oxime functional groups are important in various chemical applications, including pharmaceuticals and ligands.
Crystal engineering aims to design materials with specific properties based on intermolecular interactions.

Purpose of the Study:

To elucidate the precise molecular geometry and intermolecular interactions of the title compound, C(10)H(13)NO.
To characterize the crystal packing and hydrogen bonding network in the solid state.
To provide fundamental structural data for this organic molecule.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
Analysis of torsion angles was performed to describe the relative orientation of the benzene ring and the oxime unit.
Hydrogen bond analysis identified the specific interactions and motifs present in the crystal lattice.

Main Results:

The C-C-C-C torsion angle between the benzene ring and the butan-2-one oxime unit was determined to be 73.7(2)°.
The butan-2-one oxime moiety was found to lie above the plane of the benzene ring.
Intermolecular O-H⋯N hydrogen bonds were observed, linking molecules into dimers with R(2)(2)(6) ring motifs, which are stacked along the a axis.

Conclusions:

The crystal structure of C(10)H(13)NO is characterized by a significant torsion angle and a well-defined hydrogen bonding network.
The observed dimeric structure and stacking arrangement provide insights into the solid-state behavior of this compound.
This structural characterization contributes to the broader understanding of oxime derivatives and their crystal engineering.