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Acid-Catalyzed Hydration of Alkenes

Acid-Catalyzed Hydration of Alkenes

Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Acid Halides to Carboxylic Acids: Hydrolysis

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

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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.

Aldehydes and Ketones with Water: Hydrate Formation

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An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...

Radical Reactivity: Overview

Radical Reactivity: Overview

Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Emerging Complex Behavior Driven by Self-Organization: Dynamic Covalent Libraries of Acylhydrazones in Water.

Ferran Esteve¹, Zhaozheng Yang¹, Jean-Marie Lehn¹

¹Laboratoire de Chimie Supramoléculaire, Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Université de Strasbourg, 8 allée Gaspard Monge, 67000 Strasbourg, France.

Journal of the American Chemical Society

|July 25, 2025

Summary

Self-assembling molecules form hydrogels and microcrystals in water. These dynamic systems exhibit adaptive behaviors, including pH-responsive sorting in covalent libraries.

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Area of Science:

Supramolecular Chemistry
Materials Science

Background:

Self-organization is crucial for creating complex states of matter.
Acylhydrazone formation via condensation reactions offers a route to novel self-assembled systems.

Purpose of the Study:

To investigate the self-organization of in situ generated acylhydrazones in water.
To explore the influence of substituent polarity on the resulting self-assembled structures (hydrogels vs. microcrystals).
To demonstrate the adaptive behaviors, such as pH-responsiveness and selective imine formation, within these dynamic systems.

Main Methods:

Condensation reactions between aldehydes and hydrazides in aqueous media.
Characterization using Nuclear Magnetic Resonance (NMR) and Ultraviolet-Visible (UV-vis) spectroscopy.
Analysis of self-assembled structures via microscopy, rheology, and solid-state X-ray diffraction.

Main Results:

Acylhydrazones self-organized into hydrogels or microcrystals based on substituent properties.
Polar substituents favored hydrogel formation due to strong self-assembly of hydrophobic cores.
Microcrystalline gels with acidic/basic groups showed pH-responsiveness, enabling adaptive scrambling-sorting transitions.
Hydrophobic microenvironments within the 3D network facilitated selective imine formation by protecting reversible covalent bonds.

Conclusions:

The study demonstrates tunable self-organization of acylhydrazones into distinct phases.
pH-responsiveness and selective reactions highlight the adaptive capabilities of these dynamic covalent systems.
These self-organized systems exhibit complex adaptive behaviors, paving the way for responsive materials.