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Related Concept Videos

Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

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A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
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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...
3.4K
Alcohols from Carbonyl Compounds: Grignard Reaction02:00

Alcohols from Carbonyl Compounds: Grignard Reaction

5.2K
Grignard reagents are one of the most commonly used reagents used to synthesize alcohols from carbonyl compounds. Grignard reagents are organomagnesium halides with a highly polar carbon–magnesium bond. Due to the partial ionic nature of the C–Mg bond, the carbon functions as a strong nucleophile and attacks electrophiles like carbonyl carbon.
Magnesium from the reagent coordinates with carbonyl oxygen, further reducing the carbonyl carbon's electron density. Thus, the...
5.2K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

2.6K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

3.6K
Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
3.6K
Crossed Aldol Reaction Using Weak Bases01:14

Crossed Aldol Reaction Using Weak Bases

2.1K
This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
2.1K

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Formaldehyde surrogates in multicomponent reactions.

Cecilia I Attorresi1,2,3, Javier A Ramírez1,2, Bernhard Westermann3

  • 1CONICET - Universidad de Buenos Aires, Unidad de Microanálisis y Métodos Físicos en Química Orgánica (UMYMFOR), Ciudad Universitaria, Intendente Güiraldes 2160, Pabellón 2, 3° Piso, Ciudad Autónoma de Buenos Aires, C1428EGA, Argentina.

Beilstein Journal of Organic Chemistry
|March 18, 2025
PubMed
Summary
This summary is machine-generated.

Formaldehyde is a reactive C1-building block but poses toxicity risks and control challenges in multicomponent reactions. This review explores safer formaldehyde alternatives for improved synthesis and sustainability.

Keywords:
cascade reactionsformaldehyde surrogatesgreen chemistryheterocyclesmulticomponent reactions

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Formaldehyde is a widely used C1-building block in multicomponent reactions due to its high reactivity.
  • However, formaldehyde's toxicity and tendency to form byproducts present significant challenges in synthetic chemistry.
  • Controlling reactions involving formaldehyde can be difficult, impacting yield and purity.

Purpose of the Study:

  • To review and identify alternative C1-building blocks that can replace formaldehyde in multicomponent reactions.
  • To address the toxicity and reaction control issues associated with formaldehyde use.
  • To promote the development of more efficient and sustainable synthetic methodologies.

Main Methods:

  • Literature review of existing studies on C1-building blocks and multicomponent reactions.
  • Analysis of formaldehyde surrogates for reactivity, toxicity, and byproduct formation.
  • Evaluation of alternative C1-building blocks in the context of multicomponent reaction efficiency and sustainability.

Main Results:

  • Several alternative C1-building blocks demonstrate potential as formaldehyde surrogates.
  • These alternatives offer reduced toxicity compared to formaldehyde.
  • Improved control over byproduct formation is achievable with selected alternatives.
  • The identified alternatives can lead to more sustainable synthetic pathways.

Conclusions:

  • Alternative C1-building blocks can effectively replace formaldehyde in multicomponent reactions.
  • Adopting these alternatives mitigates toxicity concerns and enhances reaction control.
  • This shift facilitates the development of greener and more sustainable chemical synthesis.