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Related Concept Videos

Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
Noble Gases02:54

Noble Gases


The elements in group 18 are noble gases (helium, neon, argon, krypton, xenon, and radon). They earned the name “noble” because they were assumed to be nonreactive since they have filled valence shells. In 1962, Dr. Neil Bartlett at the University of British Columbia proved this assumption to be false.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

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 the...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...

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Related Experiment Video

Updated: Jun 12, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
09:08

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

Published on: February 27, 2017

The norbornene mystery revealed.

Stephan N Steinmann1, Pierre Vogel, Yirong Mo

  • 1Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne EPFL SB ISIC, Lausanne, Switzerland.

Chemical Communications (Cambridge, England)
|June 26, 2010
PubMed
Summary

The electronic structure of norbornene was clarified by comparing it to localized double bond analogues. Density redistribution suggests an impending retro-Diels-Alder reaction, solving a long-standing chemical mystery.

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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Quantum Chemistry

Background:

  • Norbornene and its derivatives exhibit unusual electronic properties that have long puzzled scientists.
  • Understanding their electronic structure is crucial for predicting reactivity and designing new molecules.

Purpose of the Study:

  • To elucidate the peculiar electronic structure of norbornene and its derivatives.
  • To investigate the nature of bonding and electron distribution within these molecules.

Main Methods:

  • Direct comparison of norbornene properties with reference compounds possessing localized double bonds (Lewis structures).
  • Block-localized wavefunction (BLW) analysis to study electron distribution.
  • Computation of Nuclear Magnetic Resonance (NMR) parameters to probe electronic environments.

Main Results:

  • The study reveals a significant density redistribution in norbornene's electronic structure.
  • BLW analysis and NMR computations provide strong evidence for this redistribution.
  • The observed electronic properties are consistent with an incipient retro-Diels-Alder reaction.

Conclusions:

  • The long-standing mystery of norbornene's electronic structure is resolved.
  • The findings support a model where electron density shifts towards a retro-Diels-Alder transition state.
  • This provides fundamental insights into the chemistry of bridged cyclic systems.