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00:56Extraction: Advanced Methods
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Metal ions can be separated from one another by complexation with organic ligands–the chelating agent– to form uncharged chelates. Here, the chelating agent must contain hydrophobic groups and behave as a weak acid, losing a proton to bind with the metal. Since most organic ligands used in this process are insoluble or undergo oxidation in the aqueous phase, the chelating agent is initially added to the organic phase and extracted into the aqueous phase. The metal-ligand complex is...
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01:26Thermal and Photochemical Electrocyclic Reactions: Overview
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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01:26Photochemical Electrocyclic Reactions: Stereochemistry
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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Selection Rules: Photochemical Activation
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01:17Thermal Electrocyclic Reactions: Stereochemistry
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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02:29Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
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Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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03:00Preparation of Epoxides
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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
9.0K
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Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
Published on: October 18, 2018
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Multiphase Methods in Organic Electrosynthesis.
Frank Marken1, Jay D Wadhawan2
1Department of Chemistry , University of Bath , Claverton Down , Bath BA2 7AY , U.K.
Accounts of Chemical Research
|November 26, 2019
Summary
This study explores water-based electrolysis for organic synthesis, focusing on methods to effectively bring poorly soluble molecules into contact with electrodes for efficient redox transformations and sustainable chemical production.
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Area of Science:
- Electrochemistry
- Organic Synthesis
- Green Chemistry
Background:
- Water is a preferred solvent for industrial and biological processes.
- Traditional electro-organic synthesis often uses organic solvents, leading to separation and reuse challenges.
- Developing water-based electrolysis for organic and biomass conversion is crucial for sustainability.
Purpose of the Study:
- To examine and compare methodologies for enabling multiphase systems in aqueous electrolysis.
- To investigate microscopic and macroscopic aspects of electrode-molecule interactions in water-based systems.
- To discuss mechanistic cases and reactor designs for multiphase redox transformations.
Main Methods:
- Utilizing physical dispersion tools (milling, ultrasound, high-shear processing) for low-solubility molecules.
- Employing cosolvents, pressurization, or surfactants to create stable multiphase conditions.
- Analyzing electrode-particle/droplet impacts and redox mediator/catalyst effects.
Main Results:
- Demonstrated benefits of aqueous electrolytes: high conductivity, simple product separation, and electrolyte reuse.
- Identified new reaction pathways and improved sustainability through multiphase electrolysis.
- Explored challenges and solutions for controlling reaction zones, including microchannel flow reactors.
Conclusions:
- Multiphase aqueous electrolysis offers a sustainable and efficient alternative for organic synthesis.
- Effective contact between dispersed phases and electrodes is key to successful redox transformations.
- Further development in reactor design is needed for scaling up multiphase electrochemical processes.