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

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

8.9K
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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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. Ethers are considered...
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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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Updated: Jan 7, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Un método general para acceder a éteres estéricamente impedidos y complejos

Sumit Pareek1, Pavan Mandadi1, Someswara Rao Sanapala1

  • 1Department of Chemistry, Indian Institute of Technology Tirupati, Yerpedu 517619, India.

The Journal of organic chemistry
|December 25, 2025
PubMed
Resumen

Un nuevo método de eterificación reductiva libre de metales sintetiza eficientemente éteres impedidos. Este proceso escalable utiliza clorodimetilsilano y un catalizador de tiourea, ofreciendo un amplio alcance de sustratos y tolerancia a grupos funcionales.

Palabras clave:
étereséteres impedidoseterificación reductivacatálisis libre de metalesclorodimetilsilanotioureasíntesis orgánicaquímica medicinal

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Área de la Ciencia:

  • Química Orgánica
  • Química Sintética
  • Catálisis

Sus antecedentes:

  • Los éteres impedidos son compuestos valiosos en química medicinal y ciencia de materiales.
  • Los métodos existentes para la síntesis de éteres impedidos a menudo requieren condiciones duras o catalizadores costosos.
  • El desarrollo de rutas sintéticas eficientes y escalables libres de metales sigue siendo un desafío clave.

Objetivo del estudio:

  • Desarrollar un método eficiente, escalable y libre de metales para la síntesis de éteres impedidos.
  • Explorar la utilidad de la catálisis de unión aniónica en la eterificación reductiva.
  • Demostrar la amplia aplicabilidad y tolerancia a grupos funcionales del nuevo método.

Principales métodos:

  • Eterificación reductiva utilizando clorodimetilsilano (CDMS) como fuente de silicio.
  • Empleo de cantidades catalíticas de tiourea de Schreiner para activar compuestos carbonílicos.
  • Utilización de HCl generado *in situ* y catálisis de unión aniónica para formar intermedios oxocarbenio.
  • Facilitación de la transferencia de hidruro para formar el enlace éter.

Principales resultados:

  • Se sintetizaron con éxito éteres impedidos con alta eficiencia utilizando un sistema catalítico libre de metales.
  • Se demostró un amplio alcance de sustratos, reaccionando con éxito 89 sustratos diferentes.
  • Se mostró una excelente tolerancia a grupos funcionales, incluyendo aplicaciones con esteroides, terpenoides, péptidos y modificación de fármacos en etapa tardía (ritonavir).

Conclusiones:

  • El método de eterificación reductiva desarrollado es eficiente, escalable y libre de metales.
  • El sistema catalítico activa eficazmente los carbonilos y promueve la formación de enlaces éter.
  • Esta metodología proporciona una herramienta versátil para la síntesis de éteres impedidos complejos relevantes para diversos campos químicos.