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Related Concept Videos

Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.6K
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...
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Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

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Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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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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Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

4.8K
Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
4.8K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.9K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
2.9K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

2.9K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
2.9K

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Related Experiment Video

Updated: Oct 4, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Acylative Kinetic Resolution of Cyclic Hydroxamic Acids.

Jingwei Yin1, Matthew R Straub1, Julian D Liao1

  • 1Department of Chemistry, Washington University, Campus Box 1134, One Brookings Drive, Saint Louis, Missouri 63130, United States.

Organic Letters
|February 11, 2022
PubMed
Summary

Racemic cyclic hydroxamic acids with adjacent aryl groups were effectively resolved using acylative kinetic resolution. Benzotetramisole (BTM) efficiently promoted this chemical transformation, enabling separation of enantiomers.

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Area of Science:

  • Organic chemistry
  • Asymmetric synthesis

Background:

  • Kinetic resolution is crucial for obtaining enantiomerically pure compounds.
  • Hydroxamic acids are versatile organic molecules with diverse applications.
  • Developing efficient methods for resolving racemic mixtures is a key challenge in synthetic chemistry.

Purpose of the Study:

  • To investigate the acylative kinetic resolution of racemic cyclic hydroxamic acids.
  • To evaluate the efficacy of benzotetramisole (BTM) as a catalyst for this process.

Main Methods:

  • Employing benzotetramisole (BTM) as a promoter for acylative kinetic resolution.
  • Utilizing racemic cyclic hydroxamic acids with aryl substituents adjacent to the hydroxyl group.

Main Results:

  • Achieved effective acylative kinetic resolution of the target compounds.
  • Demonstrated the catalytic activity of BTM in promoting the enantioselective acylation.

Conclusions:

  • Benzotetramisole (BTM) is an effective promoter for the kinetic resolution of specific cyclic hydroxamic acids.
  • This method provides a viable route for accessing enantiomerically enriched hydroxamic acid derivatives.