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Related Concept Videos

Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes02:14

Combustion Energy: A Measure of Stability in Alkanes and Cycloalkanes

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The low reactivity in alkanes can be attributed to the non-polar nature of C–C and C–H σ bonds. Alkanes, therefore, were  initially termed as “paraffins,” derived from the Latin words: parum, meaning “too little,” and affinis, meaning “affinity.”
Alkanes undergo combustion in the presence of excess oxygen and high-temperature conditions to give carbon dioxide and water. A combustion reaction is the energy source in natural gas, liquified...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Oxidative Cleavage of Alkenes: Ozonolysis01:46

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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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Original Experimental Approach for Assessing Transport Fuel Stability
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Efficient alkane oxidation under combustion engine and atmospheric conditions.

Zhandong Wang1,2,3, Mikael Ehn4, Matti P Rissanen4,5

  • 1National Synchrotron Radiation Laboratory, University of Science and Technology of China, Hefei, Anhui, 230029, P. R. China. zhdwang@ustc.edu.cn.

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Summary

Alkanes, common fuels and urban gases, undergo autoxidation more readily than expected, forming organic aerosol. This impacts combustion engine efficiency and urban air quality.

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Area of Science:

  • Atmospheric chemistry
  • Combustion science
  • Chemical kinetics

Background:

  • Oxidation chemistry governs combustion and atmospheric transformation of emissions.
  • Autoxidation, a radical chain reaction, is crucial in engines and forms atmospheric organic aerosol.
  • Alkanes were previously thought resistant to extensive autoxidation due to lacking specific functional groups.

Purpose of the Study:

  • To investigate the autoxidation efficiency of alkanes under atmospheric and combustion conditions.
  • To determine the formation of highly oxygenated products from alkanes.
  • To assess the contribution of alkane oxidation to urban organic aerosol.

Main Methods:

  • Utilized state-of-the-art mass spectrometry.
  • Measured both radical species and oxidation products.
  • Studied C6-C10 alkanes under varying conditions, including high NOX concentrations.

Main Results:

  • Alkanes demonstrate significantly higher autoxidation efficiency than previously assumed.
  • Highly oxygenated products are formed from alkanes even in the presence of high NOX.
  • Significant amounts of organic aerosol precursors are generated from alkane oxidation.

Conclusions:

  • Alkane autoxidation is a more efficient process than previously understood.
  • Alkane oxidation contributes to urban organic aerosol formation, even under polluted conditions.
  • Findings have implications for engine efficiency and urban air quality management.