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Nitriles to Ketones: Grignard Reaction

Nitriles to Ketones: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard...

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Nucleophilic Aromatic Substitution: Addition–Elimination (S_NAr)

Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...

SN2 Reaction: Transition State

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An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...

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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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Related Experiment Video

Updated: Jun 6, 2025

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

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

Published on: October 18, 2019

Skeletal Editing via Transition-Metal-Catalyzed Nitrene Insertion.

Pratibha Bhatti¹, Anjali Gupta¹, Shubham B Chaudhari¹

¹Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research, Sector-67, S. A. S., 160062, Nagar, Punjab, India.

Chemical Record (New York, N.Y.)

|November 28, 2024

Summary

Transition metal catalysis enables the efficient synthesis of nitrogen-rich compounds through single-nitrogen-atom insertion into carbocycles. This review highlights skeletal editing strategies for creating valuable N-heterocycles.

Keywords:

Molecular editing Nitrene Nitrogen heterocycles Nitrogen-atom-insertion Transition metal catalysis

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Last Updated: Jun 6, 2025

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Catalysis

Background:

Metal-nitrenes are key reactive intermediates in synthesis.
Nitrogen-rich compounds are crucial for medicinal chemistry, materials science, and industry.
Ring expansion via nitrogen atom insertion is a modern synthetic strategy.

Purpose of the Study:

To review the field of skeletal editing via single-nitrogen-atom insertion.
To focus on transition metal catalysis for N-heterocycle synthesis.
To cover nitrogen insertion across various carbocycles.

Main Methods:

Catalytic insertion of a single nitrogen atom into carbocycles.
Utilizing nitrene or metal-nitrenoid intermediates.
Employing transition metal catalysis for skeletal editing.

Main Results:

Development of efficient methods for N-heterocycle synthesis.
Access to high-value nitrogen-containing compounds from simple feedstocks.
Broad applicability of nitrogen insertion across diverse carbocyclic systems.

Conclusions:

Single-nitrogen-atom insertion is a powerful tool for constructing N-heterocycles.
Transition metal catalysis significantly advances this synthetic approach.
This methodology offers a promising route to valuable nitrogen-rich molecules.