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Ion/molecule reactions with dimethyl ether and dimethyl-d6 ether: differentiation of four isomers contained in

Bure1, Sellier, Lesage

  • 1Laboratoire de Spectrometrie de Masse, CBM, rue Charles Sadron, 45071 Orleans Cedex 02, France.

Rapid Communications in Mass Spectrometry : RCM
|May 29, 2000
PubMed

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Structure and Nomenclature of Ethers

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.
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Based on their attached substituent groups, ethers can be classified into two...
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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).
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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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The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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