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Related Concept Videos

Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

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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....
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Isomerism in Alkenes02:01

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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 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.
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Mass Spectrometry: Alkene Fragmentation00:59

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Alkenes lose one electron from the unsaturated π bond upon ionization and form stable molecular ions. Further fragmentation of alkenes occurs through three different reaction pathways. The most prominent fragmentation is the cleavage at the allylic position. The resultant allylic carbocation is resonance stabilized. In the mass spectra of terminal alkenes, this fragment appears at a mass-to-charge ratio of 41. In the internal alkenes, where there are two choices of allylic cleavage, the...
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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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A Colorimetric Method for Quantifying Cis and Trans Alkenes Using an Indicator Displacement Assay.

Stephanie A Valenzuela1, Hannah S N Crory2, Chao-Yi Yao2

  • 1Department of Chemistry, University of Texas at Austin, 100 E 24th Street, Norman Hackerman Building Room 114A, Austin, TX, 78712, USA.

Angewandte Chemie (International Ed. in English)
|March 16, 2021
PubMed
Summary

A new colorimetric assay accurately quantifies cis and trans alkenes using indicator displacement. This high-throughput method distinguishes alkene isomers with high precision, aiding chemical analysis.

Keywords:
alkene stereochemistrycolorimetric assaysdihydroxylationhigh-throughput screeninghost-guest systems

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Area of Science:

  • Analytical Chemistry
  • Organic Chemistry

Background:

  • Distinguishing between cis and trans alkene isomers is crucial in organic synthesis and analysis.
  • Existing methods for alkene isomer quantification can be time-consuming or lack high-throughput capabilities.

Purpose of the Study:

  • To develop a novel colorimetric indicator displacement assay (IDA) for high-throughput determination of cis and trans alkene percentages.
  • To establish a rapid and accurate method for alkene isomer quantification.

Main Methods:

  • A two-step protocol involving alkene dihydroxylation followed by an indicator displacement assay using boronic acid.
  • Utilized syn- and anti-addition mechanisms of dihydroxylation to generate erythro and threo vicinal diols.
  • Quantified alkene isomer ratios based on the preferential binding of threo diols to boronic acid, displacing a colorimetric indicator.

Main Results:

  • The developed IDA method accurately determined the percentage of cis and trans alkenes.
  • Blind mixtures of alkenes showed an average error of ±2% for isomer quantification.
  • Integration with E2 and Wittig reactions yielded quantification errors of ±3%.

Conclusions:

  • The colorimetric indicator displacement assay is a robust and high-throughput method for quantifying alkene isomers.
  • The assay demonstrates generality across various alkene substrates.
  • Variants of the IDA were developed to optimize color response for improved human observation.