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Related Concept Videos

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

11.2K
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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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.3K
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.
6.3K
Oxidation of Alcohols02:37

Oxidation of Alcohols

14.1K
In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
14.1K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.3K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.3K
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

13.9K
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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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.4K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Original Experimental Approach for Assessing Transport Fuel Stability
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Diastereomers and Low-Temperature Oxidation.

Aaron D Danilack1, Clayton R Mulvihill2, Stephen J Klippenstein2

  • 1Chemical and Environmental Engineering, School of Engineering, Brown University, Providence, Rhode Island 02912, United States.

The Journal of Physical Chemistry. A
|September 1, 2021
PubMed
Summary

Diastereomers, often overlooked in combustion, significantly impact low-temperature oxidation. Including them enhances reactivity and ketohydroperoxide formation in kinetic mechanisms.

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Area of Science:

  • Combustion Chemistry
  • Chemical Kinetics
  • Stereochemistry

Background:

  • Kinetic mechanisms for combustion traditionally ignore diastereomers.
  • Low-temperature oxidation kinetics is crucial for combustion and atmospheric science.
  • Stereoisomers can influence radical chain-branching pathways.

Purpose of the Study:

  • Investigate the impact of diastereomers on low-temperature oxidation kinetics.
  • Quantify the effect of stereoisomers on reaction rate coefficients.
  • Assess the influence of diastereomers on diethyl ether oxidation mechanisms.

Main Methods:

  • Replaced stereochemically unspecified intermediates and transition states with diastereomers.
  • Computed rate coefficients using ab initio transition state theory master equation calculations.
  • Performed ignition delay simulations with revised rate coefficients.

Main Results:

  • Diastereomers increased rate coefficients by factors of 1.2-1.6.
  • Inclusion of diastereomers enhanced overall mechanism reactivity by nearly 15%.
  • Peak ketohydroperoxide concentration increased by 30% in the negative temperature coefficient region.

Conclusions:

  • Stereomeric effects play a significant role in oxidation kinetics.
  • Diastereomers are important for accurate low-temperature oxidation modeling.
  • This study highlights the need to incorporate stereochemistry in kinetic mechanisms.