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Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

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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...
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Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives01:18

Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives

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Aldehydes are more reactive than carboxylic acids and hence, can get over-reduced to alcohol in the presence of strong reducing agents. Therefore, carboxylic acids are inefficient in preparing aldehydes using LAH.
Carboxylic acid derivatives like acid chlorides and esters are more easily reducible than the corresponding acids. The derivatives reduce in the presence of mild reducing agents to give aldehydes. Aldehydes can also be prepared by Rosenmund reduction, that is, the reduction of...
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Microbial Bioremediation of Pesticides01:28

Microbial Bioremediation of Pesticides

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Pesticides often feature structurally complex chemical architectures, incorporating halogen groups and multiple aromatic rings. These characteristics confer high chemical stability, rendering many pesticides resistant to natural degradation processes. This resistance poses significant environmental concerns, as persistent pesticide residues can accumulate in ecosystems and affect non-target organisms.Despite the inherent stability of many pesticides, certain microorganisms possess the metabolic...
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Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

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Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.3K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
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Development of Sulfidogenic Sludge from Marine Sediments and Trichloroethylene Reduction in an Upflow Anaerobic Sludge Blanket Reactor
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Reductive dechlorination of carbon tetrachloride using buffered alkaline ascorbic acid.

Ya-Ting Lin1, Chenju Liang1

  • 1Department of Environmental Engineering, National Chung Hsing University, 250 Kuo-Kuang Road, Taichung 402, Taiwan.

Chemosphere
|April 28, 2015
PubMed
Summary

Alkaline ascorbic acid effectively remediates carbon tetrachloride (CT) in groundwater. High pH environments, like 2M NaOH, ensure complete CT reduction without harmful byproducts, unlike phosphate buffers.

Keywords:
Alkaline ascorbic acidDichloroeliminationGroundwater remediationHydrogenolysisIn situ chemical reduction (ISCR)Vitamin C

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Area of Science:

  • Environmental Chemistry
  • Remediation Technologies
  • In-Situ Chemical Reduction (ISCR)

Background:

  • Chlorinated solvents contaminate subsurface environments.
  • Alkaline ascorbic acid (AA) is a novel reagent for in-situ chemical reduction (ISCR).
  • Maintaining alkaline pH is critical for ISCR using AA.

Purpose of the Study:

  • Investigate carbon tetrachloride (CT) reduction using alkaline AA.
  • Compare CT reduction efficacy buffered by phosphate versus NaOH.
  • Evaluate the impact of pH on CT degradation pathways and byproducts.

Main Methods:

  • Experimental study of CT reduction by alkaline AA solutions.
  • Utilized phosphate and sodium hydroxide (NaOH) buffers at pH 12.
  • Analyzed CT degradation products and AA decomposition products.
  • Observed effects of iron/soil minerals on CT reduction.

Main Results:

  • CT was reduced by AA, forming chloroform (CF) byproduct under phosphate buffering (pH 12).
  • Complete CT reduction without CF occurred in 2M NaOH.
  • Iron/soil minerals accelerated CT degradation via AA reduction and Fe(2+) precipitation.
  • High alkalinity favors dichloroelimination over hydrogenolysis for CT degradation.

Conclusions:

  • A high alkaline environment is crucial for effective CT remediation with AA.
  • 2M NaOH promotes complete CT reduction, avoiding CF byproduct formation.
  • Understanding pH-dependent pathways optimizes ISCR strategies for chlorinated solvent remediation.