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Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.4K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.4K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

3.0K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
3.0K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

1.6K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
1.6K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

9.8K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
9.8K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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

1.9K
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.
1.9K
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

3.2K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
3.2K

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Related Experiment Video

Updated: May 4, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

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Synthesis of (±)-disparlure.

J H Markgraf1, S I Lusskin, E C McDonald

  • 1Department of Chemistry, Williams College, 01267, Williamstown, Massachusetts.

Journal of Chemical Ecology
|January 11, 2014
PubMed
Summary

A new six-step synthesis creates disparlure, the gypsy moth

Area of Science:

  • Organic Chemistry
  • Insect Chemical Ecology

Background:

  • Disparlure is the sex pheromone of the gypsy moth.
  • Effective pest control strategies are crucial for managing gypsy moth populations.

Purpose of the Study:

  • To develop an efficient synthetic route for racemic disparlure.
  • To provide a reliable method for producing gypsy moth pheromone for research and application.

Main Methods:

  • A convergent synthesis approach was employed.
  • The key step involved a Wittig reaction between 6-methylheptanal and triphenylundecylphosphonium bromide.
  • Potassium carbonate and a crown ether were used as reagents.

Main Results:

  • A six-step synthesis for racemic (Z)-7,8-epoxy-2-methyloctadecane (disparlure) was successfully developed.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Last Updated: May 4, 2026

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  • The synthesis utilizes a crucial Wittig reaction for efficient coupling.
  • The method provides a viable pathway to the gypsy moth sex pheromone.

    • Conclusions:

    • The developed six-step synthesis offers an effective route to disparlure.
    • This synthesis is valuable for gypsy moth management strategies.
    • Further optimization may enhance yield and stereoselectivity.