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Preparation of Amides01:29

Preparation of Amides

4.1K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
4.1K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.5K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
4.5K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.5K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.4K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
4.4K
Microorganisms in Agriculture and Food industry01:27

Microorganisms in Agriculture and Food industry

1.6K
Microorganisms play a crucial role in agriculture and the food industry, contributing to soil fertility, crop protection, and food production. Their functions range from nitrogen fixation and biopesticide production to fermentation and food preservation, making them indispensable to sustainable farming and food safety.Role in AgricultureNitrogen-fixing bacteria, such as Rhizobium (symbiotic) and Azotobacter (free-living), convert atmospheric nitrogen into ammonia through biological nitrogen...
1.6K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.4K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
6.4K

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Related Experiment Video

Updated: Feb 14, 2026

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

12.3K

Enzymatic amidation for industrial applications.

Brent M Dorr1, Douglas E Fuerst1

  • 1Advanced Manufacturing Technologies, GlaxoSmithKline, 709 Swedeland Road, King of Prussia, PA 19406, United States.

Current Opinion in Chemical Biology
|February 8, 2018
PubMed
Summary

This review explores biocatalytic amide bond formation for industrial synthesis. While nature offers effective methods, scalability challenges limit widespread adoption of these green chemistry techniques.

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Area of Science:

  • Biocatalysis
  • Organic Synthesis
  • Green Chemistry

Background:

  • Nature provides efficient amide bond formation strategies.
  • Industrial application of biocatalysis for amide synthesis is currently limited.
  • Existing biocatalytic methods face scalability challenges.

Purpose of the Study:

  • To review demonstrated techniques for biocatalytic amide bond synthesis.
  • To examine industrial scale-up examples of these techniques.
  • To identify limitations hindering the scalability of biocatalysis in amide bond formation.

Main Methods:

  • Literature review of biocatalytic amide bond formation.
  • Analysis of industrial case studies for scale-up.
  • Identification of current technological and practical limitations.

Main Results:

  • Several biocatalytic methods for amide bond formation have been demonstrated.
  • Limited industrial scale-up successes exist, highlighting practical challenges.
  • Key limitations include enzyme stability, substrate scope, and process economics.

Conclusions:

  • Biocatalysis holds significant potential for sustainable amide bond synthesis.
  • Overcoming scalability limitations is crucial for broader industrial implementation.
  • Further research is needed to enhance enzyme performance and process efficiency.