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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...
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.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Protection of Alcohols02:31

Protection of Alcohols

This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...

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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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(E)-4-[(4-Bromo-benzyl-idene)amino]phenol.

Jasmine P Vennila, D John Thiruvadigal, Helen P Kavitha

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of a brominated organic compound, C(13)H(10)BrNO. Molecular analysis reveals a specific dihedral angle and hydrogen bonding interactions within its crystalline form.

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    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.
    • Intermolecular forces, such as hydrogen bonds and van der Waals interactions, dictate the packing of molecules in the solid state, influencing bulk material characteristics.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(13)H(10)BrNO.
    • To analyze the intermolecular interactions, including hydrogen bonding and C-H···π interactions, present in the crystal lattice.
    • To determine the dihedral angle between the two benzene rings within the molecule.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to collect diffraction data.
    • The crystal structure was solved and refined using standard crystallographic software.
    • Analysis of the crystal structure included the identification and quantification of hydrogen bonds and other non-covalent interactions.

    Main Results:

    • The crystal structure of C(13)H(10)BrNO was successfully determined.
    • A dihedral angle of 35.20(8)° was measured between the two benzene rings.
    • Molecules are interconnected via O-H⋯N hydrogen bonds, forming zigzag chains along the crystallographic a axis.
    • Weak C-H⋯π interactions were observed between adjacent molecular chains.

    Conclusions:

    • The crystal packing of C(13)H(10)BrNO is governed by a combination of O-H⋯N hydrogen bonds and C-H⋯π interactions.
    • The observed dihedral angle provides insight into the conformational preferences of the molecule in the solid state.
    • These structural findings contribute to the understanding of structure-property relationships in related organic compounds.