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Oxidation of Alcohols02:37

Oxidation of Alcohols

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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:
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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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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Properties of Organometallic Compounds01:23

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Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Reactions at the Benzylic Position: Oxidation and Reduction00:59

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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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High oxidation state bromocarbyne complexes.

Anthony F Hill1, Richard Y Kong1

  • 1Research School of Chemistry, Australian National University, Canberra, Australian Capital Territory ACT 2601, Australia. a.hill@anu.edu.au.

Chemical Communications (Cambridge, England)
|December 22, 2016
PubMed
Summary
This summary is machine-generated.

Bromination of tungsten carbyne complexes yields high oxidation state derivatives. An unprecedented bromodesilylation process was used to create a novel brominated carbyne complex.

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Area of Science:

  • Organometallic Chemistry
  • Tungsten Chemistry
  • Carbyne Complexes

Background:

  • Tungsten carbyne complexes are versatile precursors in organometallic synthesis.
  • Understanding their reactivity is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To investigate the bromination of tungsten carbyne complexes.
  • To explore novel reaction pathways for synthesizing high oxidation state tungsten derivatives.

Main Methods:

  • Reaction of [W(≡CR)Br(CO)2(dcpe)] complexes with bromine.
  • Characterization of the resulting products using spectroscopic techniques.

Main Results:

  • High oxidation state tungsten carbyne complexes [W(≡CPh)Br3(dcpe)] and [W(≡CBr)Br3(dcpe)] were synthesized.
  • An unprecedented bromodesilylation reaction was observed for the silylated carbyne complex.

Conclusions:

  • Bromination is an effective method for accessing high oxidation state tungsten carbyne complexes.
  • The discovery of bromodesilylation opens new avenues for functionalizing carbyne complexes.