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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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...

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

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...

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Acidity of 1-Alkynes

Acidity of 1-Alkynes

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.

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Related Experiment Video

Updated: Aug 7, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

From Dinitrogen to N-Containing Organic Compounds: Using Li₂ CN₂ as a Synthon.

Li-Jun Wu¹, Qianru Wang^2,3, Jianping Guo^2,3

¹Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871, China.

Angewandte Chemie (International Ed. in English)

|March 10, 2023

Summary

Researchers developed a novel method to synthesize nitrogen-containing organic compounds using lithium cyanamide (Li₂CN₂). This activated species, derived from nitrogen gas, enables efficient synthesis of valuable compounds, including potential anti-cancer agents.

Keywords:

Cycloaddition Dinitrogen Heterocycles Labeled Compounds Lithium

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Last Updated: Aug 7, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Published on: September 8, 2013

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Published on: November 9, 2019

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

Area of Science:

Organic Chemistry
Synthetic Chemistry
Materials Science

Background:

Nitrogen-containing organic compounds are crucial in pharmaceuticals and materials.
Direct synthesis from nitrogen gas (N₂) remains challenging.
Previous work established Li₂CN₂ as an activated nitrogen species from N₂, carbon, and LiH.

Purpose of the Study:

To utilize lithium cyanamide (Li₂CN₂) as a novel synthon for constructing N-containing organic compounds.
To demonstrate the versatility of Li₂CN₂ in various organic reactions.
To explore the synthesis of ¹⁵N-labeled compounds for potential applications.

Main Methods:

Application of Li₂CN₂ in substitution reactions.
Utilizing Li₂CN₂ in cycloaddition reactions.
Employing Li₂CN₂ in transition metal-catalyzed coupling reactions.

Main Results:

Successful synthesis of various cyanamides, carbodiimides, N-aryl cyanamides, and 1,2,4-triazole derivatives.
Reactions proceeded under mild conditions with moderate to excellent yields.
¹⁵N-labeled products, including anti-cancer oxazolidine derivatives, were readily prepared using ¹⁵N₂ gas.

Conclusions:

Li₂CN₂ is a versatile and effective synthon for N-containing organic compound synthesis.
The developed methodology offers a mild and efficient route to valuable nitrogenous compounds.
This approach facilitates the preparation of isotopically labeled compounds for advanced research.