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Related Concept Videos

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 Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
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...
Acidity and Basicity of Alcohols and Phenols02:36

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.
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...
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...

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Related Experiment Video

Updated: May 21, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

2-Azido-1-(4-methyl-phen-yl)ethanone.

Muhammad Arshad, Sammer Yousuf, Hafiza Madiha Butt

    Acta Crystallographica. Section E, Structure Reports Online
    |June 22, 2012
    PubMed
    Summary

    The crystal structure of C(9)H(9)N(3)O reveals specific molecular geometry, with the azide group oriented at 46.62° relative to the benzene ring. Molecules self-assemble into zigzag chains via C-H⋯O hydrogen bonds.

    Area of Science:

    • Crystallography
    • Molecular structure determination
    • Organic chemistry

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Hydrogen bonding plays a significant role in the supramolecular assembly of crystalline solids.
    • Azide functional groups introduce unique electronic and geometric characteristics to organic compounds.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(9)H(9)N(3)O.
    • To analyze the spatial orientation of the azide group relative to the benzene ring.
    • To identify and characterize intermolecular interactions, such as hydrogen bonds, governing crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.

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  • Geometric parameters, including bond angles and dihedral angles, were precisely measured.
  • Intermolecular interactions were analyzed based on crystallographic data.

    • Main Results:

    • The crystal structure of C(9)H(9)N(3)O was successfully determined.
    • The angle between the azide group's least-squares line and the normal to the benzene ring plane was found to be 46.62(16)°.
    • C-H⋯O hydrogen bonds were identified, leading to the formation of zigzag chains parallel to the [010] crystallographic direction.

    Conclusions:

    • The study provides precise crystallographic data for C(9)H(9)N(3)O.
    • The observed molecular conformation and hydrogen bonding patterns offer insights into the solid-state behavior of this compound.
    • The findings contribute to the understanding of structure-property relationships in organic azides.