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Related Concept Videos

E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

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SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Ethers to Alkyl Halides: Acidic Cleavage02:18

Ethers to Alkyl Halides: Acidic Cleavage

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Ethers are generally unreactive and unsuitable for direct nucleophilic substitution reactions since the alkoxy groups are strong bases and, therefore, poor leaving groups. However, ethers readily undergo acidic-cleavage reactions. Ethers can be converted to alkyl halides when heated with strong acids such as HBr and HI in a sequence of two substitution reactions.
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Physical Properties of Ethers02:17

Physical Properties of Ethers

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Overview
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols....
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E2 Reaction: Stereochemistry and Regiochemistry02:43

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Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
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Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

Autoxidation of Ethers to Peroxides and Hydroperoxides

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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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Preparation of Binary and Ternary Deep Eutectic Systems
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Room-Temperature Decomposition of the Ethaline Deep Eutectic Solvent.

Julia H Yang1,2, Amanda Whai Shin Ooi3, Zachary A H Goodwin2

  • 1Center for the Environment, Harvard University, Cambridge, Massachusetts 02138, United States.

The Journal of Physical Chemistry Letters
|March 17, 2025
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Ethaline, a green solvent, decomposes into toxic compounds at room temperature due to strong hydrogen bonds. Careful evaluation of hydrogen bonding is crucial for designing stable, sustainable green solvents.

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Area of Science:

  • Green Chemistry
  • Materials Science
  • Computational Chemistry

Background:

  • Environmentally benign electrolytes offer potential as green solvents and for carbon capture.
  • Ethaline (ethylene glycol and choline chloride) is a promising candidate due to its green credentials.

Purpose of the Study:

  • To investigate the decomposition of ethaline at room temperature.
  • To identify the decomposition products and understand the underlying mechanism.
  • To provide recommendations for designing stable green solvent mixtures.

Main Methods:

  • Experimental characterization of decomposition products.
  • Computational workflow using quantum chemistry to model decomposition.
  • Analysis of hydrogen bond dynamics and energy landscapes.

Main Results:

  • Ethaline partially decomposes into toxic chloromethane and dimethylaminoethanol at room temperature.
  • Strong hydrogen bonds in ethaline trap chloride ions, initiating cation-anion reactions.
  • The decomposition reaction is energetically uphill, driven by hydrogen bond stability.

Conclusions:

  • The touted green credentials of ethaline are limited by its intrinsic instability.
  • Detailed evaluation of hydrogen-bonding potential energy landscapes is essential for designing stable green solvents.
  • Further research is needed to develop truly sustainable electrolyte systems.