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Related Concept Videos

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

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.
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

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.
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

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Related Experiment Video

Updated: May 16, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Eclipsed acetaldehyde as a precursor for producing vinyl alcohol.

Osman I Osman1, Abdulrahman O Alyoubi, Shabaan A K Elroby

  • 1Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia. oabdelkarim@kau.edu.sa.

International Journal of Molecular Sciences
|December 4, 2012
PubMed
Summary

Eclipsed acetaldehyde is more stable than its bisected form due to hyperconjugative interactions. This stability was confirmed using computational chemistry methods, revealing insights into molecular conformation and reactivity.

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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Last Updated: May 16, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

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Published on: October 30, 2018

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Area of Science:

  • Quantum Chemistry
  • Computational Chemistry
  • Molecular Modeling

Background:

  • Understanding molecular conformation is crucial in chemistry.
  • Acetaldehyde exists in different spatial arrangements (conformers).
  • The relative stability of these conformers influences chemical reactions.

Purpose of the Study:

  • To investigate the origin of the stability preference of eclipsed acetaldehyde over its bisected conformer.
  • To explore the hyperconjugative interactions responsible for this preference.
  • To study the tautomeric interconversion between eclipsed acetaldehyde and vinyl alcohol.

Main Methods:

  • Utilized MP2 and Density Functional Theory (DFT/B3LYP) computational methods.
  • Employed 6-311++G(d,p) and aug-cc-pdz basis sets for calculations.
  • Performed Natural Bond Orbital (NBO) analysis to understand electronic interactions.

Main Results:

  • Determined a stability range of 1.02–1.20 kcal/mol favoring the eclipsed conformer.
  • Identified vicinal antiperiplanar hyperconjugative interactions as the primary stabilizing factor for eclipsed acetaldehyde.
  • Characterized the four-membered ring transition state for the tautomeric conversion to vinyl alcohol.

Conclusions:

  • The eclipsed conformer of acetaldehyde is inherently more stable than the bisected conformer.
  • Hyperconjugation plays a significant role in dictating the conformational preferences of acetaldehyde.
  • Computational methods provide valuable insights into molecular stability and reaction pathways.