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Related Concept Videos

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

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

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.
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction at the stage of...
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

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Related Experiment Video

Updated: May 21, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Base-Catalyzed Hydroarsination at Ambient Temperature: Synthesis in Green Solvent.

Emma J Finfer1, Noah LaMonda1, Rory Waterman1,2

  • 1Department of Chemistry, University of Vermont, Burlington, Vermont 05405, United States.

Inorganic Chemistry
|May 19, 2026
PubMed
Summary

A new, metal-free hydroarsination method uses sodium hydroxide (NaOH) to create novel tertiary arsines from simple starting materials. This accessible reaction offers improved yields and greener conditions for synthesizing diverse organoarsenic compounds.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

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Last Updated: May 21, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Area of Science:

  • Organometallic Chemistry
  • Synthetic Organic Chemistry
  • Green Chemistry

Background:

  • Hydroarsination, the addition of an arsenic-hydride bond across an unsaturated moiety, is an underdeveloped area in synthetic chemistry.
  • Existing methods often require transition metal catalysts, limiting substrate scope and increasing costs and purification complexity.
  • There is a need for practical, efficient, and environmentally friendly hydroarsination protocols.

Purpose of the Study:

  • To develop a novel, transition-metal-free hydroarsination protocol.
  • To enable the synthesis of previously inaccessible tertiary arsines.
  • To achieve regioselective anti-Markovnikov addition under mild conditions.

Main Methods:

  • Utilized a catalytic amount of commercially available, air-stable sodium hydroxide (NaOH) in dimethyl sulfoxide (DMSO).
  • Investigated the reaction with various substrates including vinylarenes, Michael acceptors, and alkynes.
  • Employed deuterium labeling studies to elucidate the reaction mechanism.

Main Results:

  • Achieved regioselective anti-Markovnikov addition of diphenylarsine to diverse unsaturated compounds at ambient temperature.
  • Synthesized previously unknown tertiary arsines in good to quantitative yields.
  • Demonstrated a nucleophilic mechanism initiated by arsine deprotonation, with NaOH playing a dual role in base activation and water management.

Conclusions:

  • The developed NaOH-catalyzed hydroarsination protocol is a practical, cost-effective, and green alternative to existing methods.
  • This methodology significantly expands the scope and accessibility of structurally diverse tertiary arsines.
  • The simplified procedure offers improved activity, broader substrate scope, and easier purification compared to prior catalysts.