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Related Concept Videos

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

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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...
Oxidation of Phenols to Quinones01:17

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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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2,9-Dichloro-1,10-phenanthroline.

Said Nadeem, Muhammad Raza Shah, Seik Weng Ng

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

    This study analyzes the molecular structure of C(12)H(6)Cl(2)N(2), revealing its near-planar configuration. The bond distances confirm significant π-electron delocalization within its aromatic fused-ring system.

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    Area of Science:

    • Crystallography and Molecular Structure
    • Organic Chemistry
    • Materials Science

    Background:

    • Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
    • Aromatic fused-ring systems are fundamental building blocks in various functional materials and pharmaceuticals.
    • Planarity and electron delocalization significantly influence a molecule's electronic and optical characteristics.

    Purpose of the Study:

    • To determine the precise molecular geometry of the title compound, C(12)H(6)Cl(2)N(2).
    • To investigate the electronic structure, specifically the extent of π-electron delocalization, within the aromatic fused-ring system.
    • To correlate the observed structural features with potential electronic properties.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to obtain the three-dimensional atomic coordinates.
    • Analysis of bond lengths (C-N and C-C) and atomic deviations from planarity were performed.
    • Computational methods were utilized to assess π-electron distribution.

    Main Results:

    • The title molecule, C(12)H(6)Cl(2)N(2), exhibits a near-planar conformation, with a root-mean-square deviation of carbon atoms of only 0.04 Å.
    • Analysis of the carbon-nitrogen (C-N) and carbon-carbon (C-C) bond distances provides evidence for significant π-electron delocalization.
    • The fused-ring aromatic system demonstrates characteristics consistent with aromaticity and extended conjugation.

    Conclusions:

    • The C(12)H(6)Cl(2)N(2) molecule possesses a highly planar structure, facilitating efficient π-electron delocalization.
    • The observed planarity and delocalized π-electron system suggest potential for interesting electronic and photophysical properties.
    • This structural characterization provides a foundation for further investigations into the functional applications of this aromatic compound.