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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
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Hydroxyacetone Production From C3 Criegee Intermediates.

Craig A Taatjes1, Fang Liu2, Brandon Rotavera1

  • 1Combustion Research Facility, Sandia National Laboratories , Livermore, California 94551-0969, United States.

The Journal of Physical Chemistry. A
|December 22, 2016
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Summary
This summary is machine-generated.

Hydroxyacetone is a stable product from acetone oxide Criegee intermediate reactions. This finding offers a reliable marker for detecting transient Criegee intermediates in future alkene ozonolysis studies.

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Area of Science:

  • Atmospheric Chemistry
  • Chemical Kinetics

Background:

  • Criegee intermediates are transient species formed during alkene ozonolysis.
  • Understanding the reaction pathways and products of Criegee intermediates is crucial for atmospheric modeling.

Purpose of the Study:

  • To identify and characterize stable end products from acetone oxide (a Criegee intermediate) reactions.
  • To investigate the formation pathways of hydroxyacetone from Criegee intermediates.
  • To establish hydroxyacetone as a potential marker for Criegee intermediate production.

Main Methods:

  • Utilized a flow tube reactor coupled with multiplexed photoionization mass spectrometry.
  • Distinguished isomers by photoionization spectra and reaction time analysis.
  • Performed electronic structure calculations to explore reaction mechanisms.

Main Results:

  • Identified hydroxyacetone as a stable end product of acetone oxide reactions.
  • Observed hydroxyacetone at longer reaction times with a higher photoionization threshold (ca. 9.7 eV).
  • Calculations indicated unimolecular isomerization and Criegee intermediate self-reaction contribute to hydroxyacetone formation.

Conclusions:

  • Hydroxyacetone is a persistent product from acetone oxide Criegee intermediate reactions.
  • Both unimolecular and self-reaction pathways contribute to hydroxyacetone formation.
  • Hydroxyacetone can serve as a stable marker for transient Criegee intermediates in alkene ozonolysis.