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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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Administering Oxygen by Mask
Administering oxygen by mask is a common nursing intervention that provides supplemental oxygen to patients with respiratory distress or chronic lung conditions. This procedure involves delivering oxygen at a specified rate through a face mask connected to an oxygen source.
Equipment
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Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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Preparation of Alcohols via Addition Reactions02:15

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The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

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Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
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Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

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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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Practical and General Alcohol Deoxygenation Protocol.

Oliver P Williams1, Alyah F Chmiel1, Myriam Mikhael2

  • 1Department of Chemistry, University of Wisconsin-Madison, Madison, WI-53706, USA.

Angewandte Chemie (International Ed. in English)
|February 25, 2023
PubMed
Summary
This summary is machine-generated.

This study presents a new photocatalytic method for removing alcohol groups using benzoate esters. The efficient deoxygenation protocol works under mild conditions and is scalable for practical applications.

Keywords:
DeoxygenationFormateMesolytic CleavagePhotoredox CatalysisReduction

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Synthetic Methodology

Background:

  • Alcohol functional groups are common in organic molecules.
  • Efficient methods for alcohol removal (deoxygenation) are valuable in synthesis.
  • Existing deoxygenation methods can be limited in scope or require harsh conditions.

Purpose of the Study:

  • To develop a practical and efficient protocol for the reductive cleavage of alcohol functional groups.
  • To establish a photocatalytic system for alcohol deoxygenation via benzoate ester reduction.
  • To enable direct alcohol deletion through a one-pot sequence.

Main Methods:

  • Development of a photocatalytic system utilizing formate salts as a reductant precursor.
  • Employing Brønsted or Lewis acids to accelerate fragmentation of the reduced intermediate.
  • Utilizing benzoate esters as precursors for alcohol functional group removal.
  • Testing the protocol on structurally diverse alcohols.

Main Results:

  • Successful deoxygenation of a wide range of structurally and electronically diverse alcohols.
  • Demonstration of a practical protocol effective under ambient air and moisture conditions.
  • Scalability of the reaction to multigram quantities.
  • Adaptation of the system for a one-pot benzoylation-deoxygenation sequence.
  • Mechanistic studies confirming the role of acidic additives in C(sp3)-O bond fragmentation.

Conclusions:

  • The developed photocatalytic system provides an efficient and practical method for alcohol deoxygenation.
  • The protocol's robustness, scalability, and mild conditions make it broadly applicable in organic synthesis.
  • The one-pot sequence offers a streamlined approach for direct alcohol deletion, simplifying synthetic routes.