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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

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Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...
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Crown Ethers02:36

Crown Ethers

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Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules...
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Ethers to Alkyl Halides: Acidic Cleavage02:18

Ethers to Alkyl Halides: Acidic Cleavage

6.9K
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.
6.9K
Alkyl Halides02:45

Alkyl Halides

19.4K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
19.4K
Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers 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.
12.4K
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

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Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Pentafluorophenyl Alkyl and Vinyl Ethers.

Walter J Pummer1, Leo A Wall1

  • 1Institute for Materials Research, National Bureau of Standards, Washington, D.C.

Journal of Research of the National Bureau of Standards. Section A, Physics and Chemistry
|December 12, 2019
PubMed
Summary
This summary is machine-generated.

Researchers synthesized new pentafluorophenetole derivatives and studied their reactions. These compounds showed varied stability towards pyrolysis, acids, and bases, with some yielding pentafluorophenol or undergoing dehydrohalogenation.

Keywords:
Ethersalkyldifluorovinylpentafluorophenoxypentafluorophenylpolymerizationpyrolysisvinyl

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Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Polymer Science

Background:

  • Pentafluorophenetole derivatives are valuable in organic synthesis.
  • Understanding their chemical behavior is crucial for developing new materials and reactions.

Purpose of the Study:

  • To synthesize novel pentafluorophenetole derivatives.
  • To investigate the reactivity of these ethers under pyrolysis, acidic, and basic conditions.
  • To explore the synthesis and polymerization of new fluorinated vinyl monomers.

Main Methods:

  • Synthesis of C6F5OCH2CH2R derivatives (R=Cl, Br, OH, OCH2CF3, OAc, OTFA).
  • Reactions studied include pyrolysis, treatment with aqueous/solid KOH, and concentrated H2SO4.
  • Synthesis and polymerization of pentafluorophenyl vinyl ether and 1,2-difluorovinyl pentafluorophenyl ether.

Main Results:

  • Ethers with β-hydrogen atoms generally yielded pentafluorophenol upon pyrolysis.
  • Basic conditions led to cleavage (aqueous KOH) or dehydrohalogenation (solid KOH).
  • Concentrated sulfuric acid cleaved most ethers, but 2-pentafluorophenoxy-1,1,1-trifluoroethane showed high resistance.

Conclusions:

  • The reactivity of pentafluorophenetole derivatives is highly dependent on their structure and reaction conditions.
  • Specific derivatives exhibit unique stability, offering potential for specialized applications.
  • New fluorinated vinyl monomers were successfully synthesized and polymerized.