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Related Concept Videos

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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.
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.

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Catalyzing aldehyde hydrosilylation with a molybdenum(VI) complex: a density functional theory study.

Paulo Jorge Costa1, Carlos C Romão, Ana C Fernandes

  • 1Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, 1749-016 Lisboa, Portugal.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 3, 2007
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Summary

Molybdenum dichloride dioxide dichloride catalyzes hydrosilylation reactions. Density functional theory calculations reveal a radical pathway may be favored over classical mechanisms, especially in solution, offering new insights into catalytic processes.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Computational Chemistry

Background:

  • [MoCl(2)O(2)] is known as an oxidation catalyst.
  • This compound also catalyzes hydrosilylation of aldehydes and ketones.
  • The catalytic mechanism was previously unclear.

Purpose of the Study:

  • To elucidate the reaction mechanism of hydrosilylation catalyzed by [MoCl(2)O(2)].
  • To investigate the Si-H activation and subsequent steps.
  • To compare classical and potential radical pathways.

Main Methods:

  • Density functional theory (DFT) calculations using the B3LYP functional.
  • Complementary experimental data.
  • Analysis of gas-phase and solvent-phase reaction pathways.

Main Results:

  • Si-H activation occurs via a [2+2] addition to the Mo=O bond, forming a hydride intermediate.
  • Two main pathways for aldehyde reduction were identified: classical and concerted.
  • Solvent effects favor the classical mechanism, while a radical pathway shows similar energy to the classical one, suggesting its potential involvement.

Conclusions:

  • The hydrosilylation mechanism catalyzed by [MoCl(2)O(2)] is complex.
  • A radical pathway is proposed as a likely mechanism in acetonitrile, aligning with experimental observations.
  • Understanding these pathways provides crucial insights for catalyst design and application.