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Related Concept Videos

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

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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 Aldehydes and Ketones from Carboxylic Acid Derivatives01:18

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Aldehydes are more reactive than carboxylic acids and hence, can get over-reduced to alcohol in the presence of strong reducing agents. Therefore, carboxylic acids are inefficient in preparing aldehydes using LAH.
Carboxylic acid derivatives like acid chlorides and esters are more easily reducible than the corresponding acids. The derivatives reduce in the presence of mild reducing agents to give aldehydes. Aldehydes can also be prepared by Rosenmund reduction, that is, the reduction of...
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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.7K
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

4.2K
Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
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Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Aldehydes as Alkylating Agents for Ketones.

Sofiya A Runikhina1, Oleg I Afanasyev1, Klim Biriukov1

  • 1Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova St. 28, 119991, Moscow, Russia.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 12, 2019
PubMed
Summary
This summary is machine-generated.

This study introduces a new, safer method for alkylating ketones using common aldehydes and carbon monoxide, catalyzed by ruthenium. This cost-effective reductive alkylation offers high yields and broad applicability for both lab and industrial settings.

Keywords:
aldehydesalpha-alkylationketonesreductive couplingruthenium

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Traditional alkylation methods often employ carcinogenic alkyl halides.
  • There is a need for safer and more sustainable alternatives in organic synthesis.

Purpose of the Study:

  • To develop a novel reductive alkylation method for ketones using non-toxic aldehydes.
  • To utilize carbon monoxide as a reducing agent in the presence of a ruthenium catalyst.

Main Methods:

  • Reductive alkylation of ketones with aldehydes.
  • Catalysis using commercially available ruthenium complex [(cymene)RuCl2]2 (250 ppm).
  • Use of carbon monoxide as the reducing agent, with or without solvent.

Main Results:

  • The reaction demonstrated a broad substrate scope, effective for aromatic and aliphatic aldehydes and ketones.
  • Nearly quantitative yields were frequently achieved.
  • The method is efficient, cost-effective, and can be performed under solvent-free conditions.

Conclusions:

  • A straightforward and green reductive alkylation protocol has been established.
  • This method offers a safer alternative to traditional alkyl halides.
  • The process is suitable for both laboratory-scale synthesis and industrial applications, utilizing waste carbon monoxide.