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Related Concept Videos

π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...
Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

Olefins, which are unsaturated hydrocarbons containing one or more carbon–carbon double bonds, are broadly divided into alkenes and cycloalkenes. The general chemical formula of an alkene is CnH2n.
Doubly bonded carbons are sp2 hybridized and have a trigonal planar geometry. The double bond is composed of a σ bond formed by the overlap of hybrid orbitals and a π bond produced by the lateral overlap of unhybridized 2p orbitals on both the carbons. Each carbon atom is bonded to two hydrogen atoms...
π Molecular Orbitals of the Allyl Radical01:27

π Molecular Orbitals of the Allyl Radical

Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons.
Intramolecular Aldol Reaction01:18

Intramolecular Aldol Reaction

Intramolecular aldol reaction occurs in dicarbonyl compounds such as dialdehydes, diketones, and keto-aldehydes. The dicarbonyl compounds possess more than one nucleophilic ⍺ carbon for the base to deprotonate and form the enolates. For example, in symmetrical diketones, there are four ⍺ carbons. Hence, four types of enolates are possible when treated with a base. However, since the molecule is symmetrical, the enolates formed on either side of one carbonyl group are equivalent to those formed...
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy radical...
Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene.  The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.

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Allenes in molecular materials.

Pablo Rivera-Fuentes1, François Diederich

  • 1Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zurich, Hönggerberg, HCI, 8093 Zurich, Switzerland.

Angewandte Chemie (International Ed. in English)
|February 7, 2012
PubMed
Summary
This summary is machine-generated.

This review explores advanced functional materials built from allenes. It covers the synthesis and properties of enantiopure allene building blocks and their diverse material applications.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Allenes are versatile organic compounds with unique electronic and structural properties.
  • The development of stable and enantiopure allene building blocks is crucial for advanced material design.
  • Allene-containing materials offer potential in various fields due to their tunable characteristics.

Purpose of the Study:

  • To provide a critical overview of allene-containing advanced functional materials.
  • To highlight the synthesis, properties, and applications of these materials.
  • To inspire novel uses of enantiopure allenes in rational material design.

Main Methods:

  • Review of literature on the design and synthesis of allene building blocks.
  • Analysis of diverse allene-containing systems such as macrocycles, foldamers, polymers, and chromophores.
  • Discussion of the properties and potential applications of these advanced materials.

Main Results:

  • Successful synthesis of stable and enantiopure allene building blocks.
  • Demonstration of allenes in various advanced functional materials including shape-persistent macrocycles, foldamers, polymers, and liquid crystals.
  • Exploration of applications in charge-transfer chromophores, dendrimers, and redox-switchable chiral chromophores.

Conclusions:

  • Enantiopure allenes are valuable synthons for creating sophisticated functional materials.
  • The discussed systems showcase the versatility and potential of allene-based materials.
  • Further research into enantiopure allenes can drive innovation in advanced materials science.