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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
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Esters to Carboxylic Acids: Saponification01:25

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Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
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Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the...
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Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It is a nucleophilic acyl substitution reaction wherein one of the ester molecules, upon deprotonation by the base, forms a nucleophilic enolate ion, while the other molecule serves as an electrophile.
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Wrapping an Ester with CO2─Until Water Breaks In.

Qing Tian1, Yue Jiang1, Jun Kang1

  • 1Department of Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing Key Laboratory of Chemical Theory and Mechanism, 401331 Chongqing, China.

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Researchers directly observed carbon dioxide (CO2) binding to methyl formate, the simplest ester. CO2 forms cage-like structures, but water can disrupt this, impacting molecular organization in CO2-rich environments.

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Area of Science:

  • Physical Chemistry
  • Chemical Physics
  • Molecular Interactions

Background:

  • Esters are crucial in carbon dioxide (CO2)-based solvents and reactions.
  • Microscopic interactions between esters and CO2 are not well understood.

Purpose of the Study:

  • To directly observe and characterize the binding and organization of CO2 around methyl formate, the simplest ester.
  • To elucidate the molecular-level mechanisms governing ester-CO2 interactions and the influence of water.

Main Methods:

  • High-resolution rotational spectroscopy.
  • Quantum-chemical analysis.
  • Investigation of binary (ester-CO2) and ternary (ester-CO2-water) clusters.

Main Results:

  • Three distinct dimer isomers of methyl formate and CO2 were identified, with varying binding motifs.
  • CO2 molecules form a cage-like network around the ester, primarily encapsulating the carbonyl site.
  • A single water molecule can displace CO2, forming cooperative interactions and altering aggregation pathways.

Conclusions:

  • This study provides the first direct insights into ester-CO2 recognition at the molecular level.
  • Molecular organization is dictated by a balance between CO2 encapsulation and water's hydrogen bonding.
  • A molecular framework is established for understanding solvation, selectivity, and reactivity in CO2-rich systems.