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Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

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.

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.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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 Hydration

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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Related Experiment Video

Updated: Jan 15, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

Published on: May 16, 2014

Alkynes and azides: beyond click chemistry.

Christina N Wiswell¹, Mitchell P Croatt¹

¹Chemistry and Biochemistry, The University of North Carolina at Greensboro, Greensboro, North Carolina, USA. mpcroatt@uncg.edu.

Chemical Communications (Cambridge, England)

|January 14, 2026

Summary

This review explores the versatile chemistry of alkynes and azides beyond copper-catalyzed azide-alkyne cycloadditions (CuAAC). It highlights mild reaction pathways to access reactive intermediates and valuable heterocyclic products for synthetic chemists.

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Last Updated: Jan 15, 2026

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

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Published on: May 16, 2014

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Reaction Mechanisms

Background:

Alkynes and azides possess weak π-bonds, enabling facile generation of high-energy reactive intermediates.
Copper-catalyzed azide-alkyne cycloadditions (CuAAC) are a prominent example of click chemistry utilizing these functionalities.

Purpose of the Study:

To review chemical transformations of alkynes and azides beyond the scope of copper-catalyzed azide-alkyne cycloadditions (CuAAC).
To explore cascade reactions and interconversions of reactive intermediates derived from alkynes and azides.
To highlight the synthetic utility and mechanistic insights offered by these reactions.

Main Methods:

Review of literature focusing on reactions involving alkynes and azides.
Analysis of reaction pathways leading to reactive intermediates.
Examination of product structures, particularly heterocycles.

Main Results:

Identification of diverse chemical reactions of alkynes and azides beyond CuAAC.
Demonstration of mild reaction conditions for accessing reactive intermediates.
Synthesis of valuable heterocyclic compounds with potential applications.

Conclusions:

The chemistry of alkynes and azides offers a broad scope for synthetic transformations.
These reactions provide mild and efficient routes to complex molecular architectures.
Expanding the repertoire beyond CuAAC significantly enhances synthetic capabilities.