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Acidity and Basicity of Alcohols and Phenols

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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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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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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...
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Benzene to Phenol via Cumene: Hock Process01:27

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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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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.
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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.
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2-(1H-Benzimidazol-2-yl)phenol.

S M Prakash1, A Thiruvalluvar2, S Rosepriya2

  • 1Research and Development Center, Bharathiar University, Coimbatore 641 046, Tamilnadu, India ; Department of Chemistry, Annamaliar College of Engineering, Mudaiyur 606 902, Tamilnadu, India.

Acta Crystallographica. Section E, Structure Reports Online
|April 26, 2014
PubMed
Summary

This study reveals the nearly planar structure of a C13H10N2O molecule, stabilized by intramolecular hydrogen bonds. Intermolecular interactions in the crystal structure include hydrogen bonds forming chains and pi-pi stacking.

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Area of Science:

  • Crystallography
  • Molecular structure analysis
  • Supramolecular chemistry

Background:

  • Understanding molecular geometry and intermolecular interactions is crucial for predicting material properties.
  • Planar molecules and hydrogen bonding are key features in crystal engineering.

Purpose of the Study:

  • To characterize the crystal structure and intermolecular interactions of the title molecule C13H10N2O.
  • To investigate the planarity, hydrogen bonding, and pi-pi stacking in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond distances, angles, dihedral angles, and non-covalent interactions was performed.

Main Results:

  • The title molecule C13H10N2O exhibits a nearly planar conformation with minimal deviation from the plane.
  • An intramolecular hydrogen bond forms a stable S(6) ring motif.
  • Intermolecular N-H⋯O hydrogen bonds link molecules into chains, and four distinct pi-pi stacking interactions are observed in the crystal lattice.

Conclusions:

  • The crystal structure is stabilized by a combination of intramolecular and intermolecular hydrogen bonds, as well as pi-pi stacking.
  • The observed planarity and specific intermolecular interactions dictate the overall crystal packing and potential material properties.