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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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Redox Titration: Other Oxidizing and Reducing Agents01:26

Redox Titration: Other Oxidizing and Reducing Agents

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Besides iodine, other oxidizing or reducing agents can serve as titrants in redox titrations. Common oxidizing titrants include KMnO4, cerium(IV), and K2Cr2O7. The choice of oxidizing titrants depends on factors like stability, cost, analyte strength, and reaction rate between the analyte and titrant. KMnO4 is a strong oxidizing titrant that reduces from Mn(VII) to Mn(II) in a highly acidic solution, simultaneously oxidizing the analyte to a higher oxidation state. In this case, KMnO4 acts as a...
346
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.8K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
3.8K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

2.9K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
2.9K
Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

3.6K
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
3.6K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.6K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Light-driven Enzymatic Decarboxylation
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The Reducing Agents in Sonochemical Reactions without Any Additives.

Kyuichi Yasui1

  • 1National Institute of Advanced Industrial Science and Technology (AIST), Nagoya 463-8560, Japan.

Molecules (Basel, Switzerland)
|May 27, 2023
PubMed
Summary

Ultrasound in water generates reducing agents like H and H2 from bubbles, capable of reducing metal ions to nanoparticles. Hydrated electrons may also play a key role in these sonochemical reduction reactions.

Keywords:
H atomsan air or argon bubblebubble collapsechemical reactionsnumerical simulationsreducing agentssonochemistryultrasoundwater vapor

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Area of Science:

  • Physical Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Ultrasound induces oxidation and reduction reactions in aqueous solutions without additives.
  • Cavitation bubbles under ultrasound generate various reducing species.

Purpose of the Study:

  • To investigate the reducing agents produced during sonolysis of aqueous solutions.
  • To explore the potential of these agents in reducing metal ions for nanoparticle synthesis.
  • To discuss the influence of ultrasonic frequency on radical generation.

Main Methods:

  • Numerical simulations of chemical reactions within cavitation bubbles.
  • Analysis of reduction potentials of generated species.
  • Experimental reporting on sonochemical reduction.

Main Results:

  • Key reducing agents identified: H, H2, HO2 (superoxide anion), NO, HNO2 (nitrite anion), and sometimes H2O2.
  • H and H2 are potent reducers for metal ions, especially in alkaline solutions, facilitating metal nanoparticle formation.
  • Hydrated electrons (e-aq) and superoxide anions (O2-) may contribute to sonochemical reduction.

Conclusions:

  • Sonolysis of water generates effective reducing species for nanoparticle synthesis.
  • The type and concentration of reducing agents depend on conditions like pH and ultrasonic frequency.
  • Further research into hydrated electrons and superoxide anions in sonochemistry is warranted.