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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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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...
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Acid-Catalyzed Aldol Addition Reaction01:15

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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
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Reactions of Carboxylic Acids: Introduction01:41

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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

3.2K
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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Polythionic Acids in the Wackenroder Reaction.

Elvira Spatolisano1, Laura A Pellegrini1, Simone Gelosa2

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This study investigates the laboratory-scale production of polythionates, crucial compounds in sulfur chemistry and industrial applications like soil improvement. Research focuses on optimizing conditions for the HydroClaus process, enhancing sulfur-based soil amendments.

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Area of Science:

  • Inorganic Chemistry
  • Environmental Chemistry
  • Materials Science

Background:

  • Polythionic acids (H2SnO6, n>2) are reactive sulfur compounds found in Wackenroder liquid.
  • They have diverse technical applications including gold leaching and metal processing.
  • Industrial processes now utilize biological and chemical methods to convert hydrogen sulfide (H2S) into sulfur and polythionate mixtures for soil improvement.

Purpose of the Study:

  • To study the laboratory-scale production of polythionates for the industrial scale-up of the HydroClaus process.
  • To optimize reaction conditions for efficient polythionate synthesis.
  • To analyze the impact of operating conditions on product distribution and nature.

Main Methods:

  • Literature review on polythionate synthesis and characterization.
  • Synthesis of sulfur-based mixtures containing polythionates.
  • Determination of polythionate ion concentration.
  • Investigation of reaction parameters affecting product yield and speciation.

Main Results:

  • Established a laboratory-scale synthesis of polythionates.
  • Quantified polythionate concentrations in the synthesized mixtures.
  • Identified key reaction conditions influencing polythionate formation and distribution.

Conclusions:

  • The study provides foundational data for scaling up the HydroClaus process.
  • Optimized polythionate production is key for developing effective sulfur-based soil improvers.
  • Understanding reaction dynamics is crucial for industrial application of polythionate chemistry.