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Related Concept Videos

Preparation of Epoxides03:00

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 Epoxides02:38

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...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Structure and Nomenclature of Ethers02:28

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...
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

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Related Experiment Video

Updated: Jun 1, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Published on: February 6, 2019

(E)-3,5-Dimeth-oxy-benzaldehyde oxime.

Bin Dong, Yu Zhang, Jin-Zhe Chen

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a novel compound, C(9)H(11)NO(3). Molecules form chains via hydrogen bonds, deviating from typical oxime dimer arrangements observed in chemical crystallography.

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    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Understanding molecular interactions and packing in organic compounds is crucial for predicting material properties.
    • Oxime functional groups exhibit specific hydrogen bonding patterns in crystalline solids.
    • The dimethoxyl-benzene moiety influences molecular conformation and intermolecular interactions.

    Purpose of the Study:

    • To elucidate the crystal structure and intermolecular interactions of the title compound, C(9)H(11)NO(3).
    • To investigate the conformational characteristics of the oxime group relative to the dimethoxyl-benzene ring.
    • To compare the observed crystal packing with common oxime motifs.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular and crystal structure.
    • Geometric parameters, including bond lengths, bond angles, and torsion angles, were analyzed.
    • Hydrogen bonding networks and their associated graph-set motifs were identified and characterized.

    Main Results:

    • The crystal structure of C(9)H(11)NO(3) was determined, revealing a significant twist (12.68°) of the oxime group relative to the dimethoxyl-benzene ring.
    • Molecules are organized into infinite [100] chains through intermolecular O-H⋯N hydrogen bonds.
    • This chain motif represents a departure from the frequently observed dimeric oxime packing.

    Conclusions:

    • The study provides detailed structural insights into C(9)H(11)NO(3), highlighting a unique hydrogen bonding arrangement.
    • The observed crystal packing demonstrates an alternative to common oxime dimerization, offering new perspectives in supramolecular chemistry.
    • The findings contribute to the understanding of structure-property relationships in organic crystalline materials.