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Related Concept Videos

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...
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.
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.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Related Experiment Video

Updated: Jun 1, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

[2-(2,3-Dimethyl-anilino)phen-yl]methanol.

Nasirullah, Nazar Ul Islam, M Nawaz Tahir

    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 C(15)H(17)NO compound, revealing a disordered 2,3-dimethyl-phenyl group and intramolecular hydrogen bonding. The findings contribute to understanding molecular arrangements in organic crystals.

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    Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

    Published on: June 13, 2022

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Supramolecular Chemistry

    Background:

    • Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Crystal structure analysis provides detailed insights into molecular conformation, intermolecular interactions, and packing in the solid state.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(15)H(17)NO.
    • To characterize the disorder, planarity, and dihedral angles of the molecular components.
    • To identify and describe hydrogen bonding and other non-covalent interactions stabilizing the crystal.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of atomic coordinates and bond lengths/angles provided information on molecular geometry.
    • Intermolecular and intramolecular interactions were identified using hydrogen bond analysis and non-covalent interaction analysis.

    Main Results:

    • The 2,3-dimethyl-phenyl group exhibits positional disorder with an occupancy ratio of approximately 0.87:0.13.
    • The 2,3-dimethyl-anilino group is planar in both major and minor disordered components.
    • An intramolecular N-H⋯O hydrogen bond forms an S(6) ring motif, and intermolecular O-H⋯O hydrogen bonds link molecules into chains along the b axis.

    Conclusions:

    • The crystal structure of C(15)H(17)NO is characterized by significant disorder in the 2,3-dimethyl-phenyl group.
    • Intramolecular and intermolecular hydrogen bonding play key roles in stabilizing the molecular and supramolecular architecture.
    • The identified C-H⋯π interactions further contribute to the overall crystal packing and stability.