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Related Concept Videos

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

7.2K
The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

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...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

3.8K
α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
3.8K
Phase II Conjugation Reactions: Overview01:14

Phase II Conjugation Reactions: Overview

1.3K
Conjugation, a key component of phase II biotransformation reactions, is a vital process in drug detoxification. It involves transferring endogenous substances like glucuronic acid, sulfate, and glycine to drugs or their metabolites formed in phase I reactions. These conjugation reactions, often catalyzed by specific enzymes, transform potentially harmful metabolites into inactive, water-soluble forms easily excreted in urine or bile. By enhancing polarity and eliminating pharmacological...
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Related Experiment Video

Updated: May 6, 2026

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
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Stabilized Wittig olefination for bioconjugation.

Kenneth M Lum1, Vanessa J Xavier, Michelle J-H Ong

  • 1Division of Organic Chemistry, Institute of Chemical and Engineering Sciences, Agency for Science Technology and Research Singapore, 11 Biopolis Way, Helios Block #03-08, Singapore. chan_kok_ping@ices.a-star.edu.sg.

Chemical Communications (Cambridge, England)
|October 24, 2013
PubMed
Summary
This summary is machine-generated.

Stabilized Wittig olefination enables robust bioconjugation. This reaction allows for live cell protein tagging and isolation, demonstrated using FKBP12 protein.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Bioconjugation Techniques

Background:

  • The Wittig reaction is a fundamental organic transformation for creating carbon-carbon double bonds.
  • Bioconjugation, the linking of biomolecules, is crucial for biological research and diagnostics.
  • Developing efficient and specific bioconjugation methods is an ongoing challenge in chemical biology.

Purpose of the Study:

  • To explore the potential of stabilized Wittig olefination as a novel bioconjugation strategy.
  • To demonstrate the applicability of this reaction for in-cell protein modification and analysis.

Main Methods:

  • Utilized stabilized phosphorus ylides and aryl aldehydes for olefination reactions.
  • Applied the reaction to live cells for protein labeling and isolation.
  • Employed fluorescence tagging for visualization and affinity isolation of target proteins.

Main Results:

  • The stabilized Wittig olefination proved robust under physiological conditions.
  • Successfully achieved in-cell fluorescence tagging of the FKBP12 protein.
  • Demonstrated the utility of the reaction for live cell affinity isolation of proteins.

Conclusions:

  • Stabilized Wittig olefination is a viable and effective method for bioconjugation.
  • This approach offers a powerful tool for live cell protein manipulation and study.
  • The reaction's robustness supports its application in complex biological systems.