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Related Concept Videos

[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.
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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.
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Published on: December 16, 2022

(Cyclo-pentane-1,1-di-yl)dimethanol.

Richard Betz1, Peter Klüfers, Peter Mayer

  • 1Ludwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13 (Haus D), 81377 München, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

The study reveals how molecules of C(7)H(14)O(2) form strands through hydrogen bonds, creating specific ring structures. This molecular arrangement influences the compound

Area of Science:

  • Crystal Engineering
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding intermolecular forces is crucial for designing materials.
  • Hydrogen bonding plays a key role in molecular self-assembly.
  • Crystal structure analysis provides insights into molecular interactions.

Purpose of the Study:

  • To investigate the crystal structure of the compound C(7)H(14)O(2).
  • To analyze the hydrogen bonding patterns and their role in molecular assembly.
  • To determine the conformation of the cyclopentane ring within the crystal structure.

Main Methods:

  • Single-crystal X-ray diffraction was used to determine the molecular structure.
  • Graph-set analysis was employed to characterize the hydrogen bonding motifs.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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  • Conformational analysis was performed on the cyclopentane ring.

    • Main Results:

    • Molecules self-assemble into strands along the [100] direction via O-H⋯O hydrogen bonds.
    • Co-operative eight-membered homodromic rings, described by R(4)(4)(8), are formed.
    • The cyclopentane ring adopts an envelope conformation, denoted as (C4)E.

    Conclusions:

    • The study elucidates the supramolecular architecture of C(7)H(14)O(2) driven by hydrogen bonding.
    • The identified hydrogen bonding network and ring structures are key features of the crystal packing.
    • The specific ring conformation impacts the overall crystal structure and molecular arrangement.