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Related Concept Videos

Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Preparation of Acid Anhydrides01:07

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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
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Reactions of Acid Anhydrides01:19

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The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
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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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Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

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Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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Malonic Anhydrides, Challenges from a Simple Structure.

Charles L Perrin1

  • 1Department of Chemistry, University of California─San Diego, La Jolla, California 92093-0358, United States.

The Journal of Organic Chemistry
|May 18, 2022
PubMed
Summary
This summary is machine-generated.

Monomeric malonic anhydrides were successfully synthesized via ozonolysis of ketene dimers. These unstable compounds decompose rapidly, with substituted derivatives exhibiting varied decomposition rates explained by computational analysis.

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Area of Science:

  • Organic Chemistry
  • Chemical Synthesis
  • Physical Chemistry

Background:

  • Monomeric malonic anhydrides have long been challenging to synthesize.
  • Previous attempts at preparation were unsuccessful.

Purpose of the Study:

  • To report the first successful synthesis of monomeric malonic anhydrides.
  • To characterize the stability and decomposition kinetics of these compounds.

Main Methods:

  • Ozonolysis of ketene dimers was employed for synthesis.
  • Infrared (IR) and Raman spectroscopy were used for structural elucidation.
  • Kinetic studies and computational analysis were performed to understand decomposition.

Main Results:

  • Monomeric malonic anhydrides were successfully prepared and characterized.
  • These anhydrides are unstable, decomposing below room temperature into ketene and carbon dioxide.
  • The dimethyl derivative was slightly more stable than the parent compound.
  • The monomethyl derivative exhibited the fastest decomposition rate, with a low enthalpy of activation (12.6 kcal/mol).

Conclusions:

  • The synthesis of monomeric malonic anhydrides is now achievable.
  • Decomposition follows a concerted [2s + 2a] cycloreversion pathway.
  • Computational studies rationalize the observed stability trends based on transition state organization.