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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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Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

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The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Updated: Mar 30, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Metal catalyzed defunctionalization reactions.

Atanu Modak1, Debabrata Maiti1

  • 1Department of Chemistry, Indian Institute of Technology, Powai, Mumbai, 400076, India. dmaiti@chem.iitb.ac.in.

Organic & Biomolecular Chemistry
|November 14, 2015
PubMed
Summary
This summary is machine-generated.

Metal-assisted defunctionalization reactions are crucial for creating valuable products and enabling synthetic chemistry. This review details their historical progression from stoichiometric to catalytic methods, aiding organic synthesis.

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Area of Science:

  • Synthetic organic chemistry
  • Catalysis
  • Reaction mechanisms

Background:

  • Defunctionalization impacts value-added product synthesis, such as biomass degradation.
  • In synthetic chemistry, functional groups can serve as transient directing groups.
  • Metal-assisted reactions offer unique pathways for chemical transformations.

Purpose of the Study:

  • To provide a chronological overview of metal-assisted defunctionalization reactions.
  • To illustrate the evolution from stoichiometric to catalytic approaches.
  • To explain the applications of these reactions in synthetic organic chemistry.

Main Methods:

  • Literature review of metal-assisted defunctionalization reactions.
  • Analysis of historical development and applications.
  • Description of proposed catalytic cycles for key transformations.

Main Results:

  • Documented the historical progression of metal-assisted defunctionalization.
  • Highlighted the shift from stoichiometric to catalytic methods.
  • Presented applications in synthesizing value-added products and enabling complex organic synthesis.

Conclusions:

  • Metal-assisted defunctionalization has evolved significantly, offering powerful tools for organic synthesis.
  • Catalytic methods represent a more efficient and sustainable approach.
  • Understanding reaction mechanisms and catalytic cycles is key to their effective application.