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Related Concept Videos

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.

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Related Experiment Video

Updated: May 11, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Published on: June 21, 2017

Computational investigations on base-catalyzed diaryl ether formation.

Gavin O Jones1, Ali Al Somaa, Jeannette M O'Brien

  • 1IBM Almaden Research Center, 650 Harry Road, San Jose, California 95120, United States.

The Journal of Organic Chemistry
|May 8, 2013
PubMed
Summary

This study reveals that metal cations facilitate polyether formation by binding leaving groups, and larger cations lower reaction barriers. Understanding these reaction mechanisms is key for optimizing synthetic routes.

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Published on: November 27, 2015

Area of Science:

  • Computational Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Polyether formation is crucial for synthesizing various materials.
  • Understanding reaction mechanisms guides the development of efficient synthetic strategies.

Purpose of the Study:

  • Investigate the mechanisms and energetics of polyether formation reactions.
  • Model reactions using group I metal phenoxides and halobenzenes.
  • Analyze the influence of substituents and metal cations on reaction rates.

Main Methods:

  • Utilized dispersion-corrected B3LYP density functional method for calculations.
  • Examined reactions of group I metal phenoxides with para-substituted halobenzenes.
  • Applied the distortion/interaction energy theory model.

Main Results:

  • Calculated activation barriers correlate with substituent electronic properties.
  • The major activation energy component is reactant distortion.
  • Metal cations facilitate reactions by binding leaving groups, not by increasing rate.
  • Larger metal cations decrease reaction barriers by reducing phenoxide distortion.

Conclusions:

  • Reaction rates are influenced by substituent effects and metal cation size.
  • Distortion/interaction energy theory explains activation energy trends.
  • Metal cations play a vital role in facilitating leaving group displacement.