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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...
Catalysis02:50

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

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Related Experiment Video

Updated: May 31, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Dinitrogen silylation and cleavage with a hafnocene complex.

Scott P Semproni1, Emil Lobkovsky, Paul J Chirik

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

Journal of the American Chemical Society
|June 21, 2011
PubMed
Summary

This study demonstrates the synthesis of formamide from dinitrogen, carbon monoxide, and an organosilane using a hafnocene complex. The process involves silylation, N-N bond cleavage, and carbonylation, showcasing a novel route to organic molecules.

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Catalysis

Background:

  • Dinitrogen (N2) activation remains a significant challenge in chemistry.
  • Hafnocene complexes offer unique reactivity for small molecule activation.
  • Organosilanes are versatile reagents in synthetic chemistry.

Purpose of the Study:

  • To investigate the silylation of a hafnocene dinitrogen complex.
  • To explore the cleavage of the dinitrogen ligand.
  • To synthesize organic molecules from N2 and CO.

Main Methods:

  • Silylation of a hafnocene dinitrogen complex with CySiH3.
  • Thermal activation of the silylated intermediate.
  • Carbonylation of the dinitrogen cleavage product.
  • Acidic workup to yield the final organic product.

Main Results:

  • Formation of N-Si and Hf-H bonds during silylation.
  • N-N bond scission triggered by silyl migration upon warming.
  • Synthesis of an unprecedented μ-formamidide ligand via carbonylation.
  • Liberation of formamide after treatment with HCl.

Conclusions:

  • Demonstrated a novel method for dinitrogen cleavage and functionalization.
  • Successfully synthesized formamide from abundant small molecules (N2, CO) and an organosilane.
  • Highlights the potential of hafnocene complexes in sustainable synthesis.