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Related Concept Videos

Acidity and Basicity of Alcohols and Phenols02:36

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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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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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...
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Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

17.3K
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...
17.3K
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

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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.
As with other organic compounds, alcohols and...
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Reactivity of Enolate Ions01:23

Reactivity of Enolate Ions

3.5K
Enolate ions are formed by the acid–base reaction of a carbonyl compound with a base. This leads to deprotonation of the α hydrogen atom, leading to a resonance-stabilized enolate ion where one of the contributing structures is an oxyanion, which imparts additional stability. Therefore, the proton on the α carbon is more acidic in nature than that of other sp3-hybridized C–H bonds but less acidic than those in O–H bonds where the negative charge in the conjugate...
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Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

3.7K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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CO2 Chemistry of Phenolate-Based Ionic Liquids.

Tae Bum Lee1, Seungmin Oh1, Thomas R Gohndrone1

  • 1Department of Chemical and Biomolecular Engineering, University of Notre Dame , Notre Dame, Indiana 46556, United States.

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|November 12, 2015
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We synthesized phosphonium-based ionic liquids (ILs) for CO2 capture. Ylide formation, not anion interaction, drives CO2 uptake, offering a novel pathway for carbon capture technologies.

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Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature
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Area of Science:

  • Materials Science
  • Chemical Engineering
  • Physical Chemistry

Background:

  • Ionic liquids (ILs) are promising materials for CO2 capture.
  • Understanding the CO2 interaction mechanism with ILs is crucial for optimizing their performance.

Purpose of the Study:

  • To synthesize and characterize novel alkylphosphonium-based ionic liquids with phenolate anions.
  • To elucidate the reaction mechanism of CO2 with these ILs using computational and experimental methods.
  • To evaluate the CO2 solubility and physical properties of the synthesized ILs.

Main Methods:

  • Synthesis of ionic liquids with alkylphosphonium cations and phenolate, 4-nitrophenolate, and 4-methoxyphenolate anions.
  • Characterization using spectroscopic techniques (ATR-FTIR, 31P NMR).
  • Determination of physical properties (viscosity, conductivity, CO2 solubility).
  • Computational quantum chemistry modeling to reveal reaction mechanisms.

Main Results:

  • Ionic liquids were successfully synthesized and characterized.
  • Physical properties including viscosity, conductivity, and CO2 solubility were measured.
  • Computational modeling and spectroscopic data revealed that CO2 reacts with phenolate-based ILs via phosphonium ylide formation.
  • Ylide formation, involving deprotonation of the phosphonium cation, is the primary mechanism for CO2 uptake, not direct anion-CO2 interaction.

Conclusions:

  • The study identifies phosphonium ylide formation as the key mechanism for CO2 capture in phenolate-based ionic liquids.
  • This finding provides a new perspective on designing ILs for efficient carbon capture.
  • The synthesized ILs demonstrate potential for practical applications in CO2 separation and utilization.