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Related Concept Videos

Nomenclature of Alkenes02:29

Nomenclature of Alkenes

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The IUPAC naming system for alkenes replaces -an- with -en- in the corresponding parent alkanes. Accordingly, a simple alkene replaces the -ane suffix of the alkane with -ene.
As per the IUPAC rules, the longest carbon chain containing the maximum number of double bonds is identified as the parent chain and is numbered such that the doubly bonded carbon atoms receive the lowest possible numbers. The location of the double bond is indicated by the number of its first carbon atom. In branched...
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Isomerism in Alkenes02:01

Isomerism in Alkenes

14.7K
Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
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Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Structure and Bonding of Alkenes02:47

Structure and Bonding of Alkenes

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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...
20.3K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

14.7K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

15.6K
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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Oxo-Thiolation of Cationically Polymerizable Alkenes Using Flow Microreactors.

Yosuke Ashikari1, Kodai Saito2, Toshiki Nokami3

  • 1Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 16, 2019
PubMed
Summary
This summary is machine-generated.

This study introduces cationic oxo-thiolation of polymerizable alkenes using anodic oxidation. Fast mixing in flow microreactors enhances chemoselectivity and allows for higher reaction temperatures.

Keywords:
alkenesanodic oxidationcationicselectrochemistryflow microreactorspolymerization

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Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Electrochemistry

Background:

  • Cationic polymerization is a common method for alkene functionalization.
  • Controlling chemoselectivity in alkene reactions can be challenging.
  • Anodic oxidation offers a route to generate reactive cationic species.

Purpose of the Study:

  • To develop a novel method for cationic oxo-thiolation of polymerizable alkenes.
  • To investigate the use of anodic oxidation for generating reactive cationic species.
  • To control chemoselectivity and reaction conditions using flow microreactors.

Main Methods:

  • Generation of highly reactive cationic species via anodic oxidation.
  • Activation of polymerizable alkenes by these cationic species.
  • Utilizing fast mixing in flow microreactors for reaction control.

Main Results:

  • Successful cationic oxo-thiolation of polymerizable alkenes was achieved.
  • Highly reactive cations were generated and effectively activated alkenes.
  • Flow microreactors enabled precise control over chemoselectivity.
  • Higher reaction temperatures were feasible due to controlled conditions.

Conclusions:

  • Anodic oxidation provides an efficient method for generating reactive cations for oxo-thiolation.
  • Flow microreactor technology is crucial for controlling selectivity and enabling demanding reaction conditions.
  • This approach offers a new pathway for functionalizing polymerizable alkenes with improved control.