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Related Concept Videos

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

8.8K
Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

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Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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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.
19.7K
Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

22.3K
In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
22.3K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

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Alkene hydrofunctionalization using hydroxamic acids: a radical-mediated approach to alkene hydration.

Benjamin C Giglio1, Erik J Alexanian

  • 1Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States.

Organic Letters
|July 29, 2014
PubMed
Summary

This study introduces a novel radical-mediated alkene hydration method using hydroxamic acids. These compounds act as both radical sources and hydrogen donors, enabling efficient alkene functionalization and cyclization reactions.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Radical Reactions

Background:

  • Alkene hydration is a fundamental transformation in organic synthesis.
  • Developing efficient and versatile methods for alkene functionalization remains a key challenge.
  • Radical-mediated reactions offer unique reactivity pathways distinct from polar mechanisms.

Purpose of the Study:

  • To develop a novel radical-mediated approach for alkene hydration.
  • To utilize the dual role of hydroxamic acids as radical precursors and hydrogen atom donors.
  • To explore the application of this methodology in tandem carbocyclization reactions.

Main Methods:

  • Employing hydroxamic acids as key reagents in radical reactions.
  • Utilizing a radical initiation strategy to generate oxygen-centered radicals from hydroxamic acids.
  • Investigating the scope and limitations of the developed alkene hydration protocol.
  • Applying the method to construct carbocyclic frameworks via tandem reactions.

Main Results:

  • Successful demonstration of a radical-mediated alkene hydration reaction.
  • Hydroxamic acids effectively serve as both radical oxygen sources and hydrogen atom donors.
  • The methodology is applicable to a range of alkene substrates.
  • Tandem alkene-alkene carbocyclization processes were achieved.

Conclusions:

  • A new, efficient radical-mediated pathway for alkene hydration has been established.
  • Hydroxamic acids represent a versatile tool for radical-based synthetic transformations.
  • The developed method provides a valuable addition to the synthetic chemist's toolkit for alkene functionalization and carbocycle synthesis.