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Related Concept Videos

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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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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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
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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.
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In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
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Esterification of Aryl/Alkyl Acids Catalysed by

Klara Čebular1,2,3, Bojan Đ Božić4,5, Stojan Stavber6,7,8

  • 1Centre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins, Jamova 39, 1000 Ljubljana, Slovenia. klara.cebular@ijs.si.

Molecules (Basel, Switzerland)
|September 12, 2018
PubMed
Summary

N-bromosuccinimide (NBS) efficiently catalyzes direct esterification of carboxylic acids. This metal-free method offers high yields and simple procedures for synthesizing aromatic and alkyl esters.

Keywords:
N-halosuccinimidealkyl acidsaryl acidsesterificationmetal-free catalyst

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Area of Science:

  • Organic Chemistry
  • Green Chemistry

Background:

  • N-halosuccinimides (NXSs) are common halogenation reagents.
  • Direct esterification is a crucial transformation in organic synthesis.

Purpose of the Study:

  • To identify the most effective NXS catalyst for direct esterification.
  • To develop a metal-free, efficient, and scalable esterification protocol.

Main Methods:

  • Screening of various N-halosuccinimides (NXSs) as catalysts.
  • Direct esterification of aryl and alkyl carboxylic acids under neat conditions.
  • Optimization of reaction parameters for efficiency and selectivity.

Main Results:

  • N-bromosuccinimide (NBS) demonstrated superior catalytic activity and selectivity.
  • High yields (up to 100%) achieved for a wide range of aromatic and alkyl esters.
  • The protocol is metal-free, air- and moisture-tolerant, facilitating simple isolation and scale-up.

Conclusions:

  • N-bromosuccinimide is an excellent catalyst for direct esterification.
  • The developed method offers a sustainable and efficient route to ester synthesis.
  • A catalyst recycling protocol was successfully proposed.