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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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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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Reactivity of Enols

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Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
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α-Alkylation of Ketones via Enolate Ions01:10

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Alkyl Enol Ethers: Development in Intermolecular Organic Transformation.

Sarwat Asma Ziya Ahmad1, Tapan Kumar Jena1, Faiz Ahmed Khan1

  • 1Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502285, India.

Chemistry, an Asian Journal
|May 12, 2021
PubMed
Summary

Alkyl enol ethers (AEE) are valuable building blocks in organic synthesis. This review highlights their synthesis, ambiphilic reactivity, and diverse applications in forming new bonds and complex molecules.

Keywords:
Alkyl enol ethersIntermolecular reactionsambiphilic nature

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Alkyl enol ethers (AEE) are recognized as versatile synthetic intermediates.
  • Their unique reactivity patterns enable diverse chemical transformations.

Purpose of the Study:

  • To comprehensively review the synthesis and reactivity of alkyl enol ethers.
  • To emphasize the extensive intermolecular reaction capabilities of AEE with both electrophiles and nucleophiles.
  • To highlight the synthetic potential of AEE in constructing complex organic molecules.

Main Methods:

  • Literature review of synthetic methodologies for AEE.
  • Analysis of reported intermolecular reactions involving AEE.
  • Compilation of AEE applications in metal-catalyzed reactions, cycloadditions, heterocycle formation, and natural product synthesis.

Main Results:

  • AEE exhibit ambiphilic behavior, reacting readily with both electrophiles and nucleophiles.
  • Intermolecular reactions of AEE are crucial for various bond formations.
  • AEE are instrumental in synthesizing diverse organic molecules, including natural products.

Conclusions:

  • Alkyl enol ethers possess significant synthetic potential due to their ambiphilic nature.
  • Further exploration of AEE's intermolecular reactivity is warranted.
  • This review aims to increase awareness and encourage further research in AEE chemistry.