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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...

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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,...

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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...

Acid-Catalyzed Dehydration of Alcohols to Alkenes

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In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.

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.

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

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As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.

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Ru-catalyzed deoxydehydration (DODH) with hydrazine.

Siyi Luo¹, Chen-Chen Li¹, Zihang Qiu¹

¹Department of Chemistry, and FRQNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, Quebec H3A 0B8, Canada. cj.li@mcgill.ca.

Chemical Communications (Cambridge, England)

|September 15, 2025

Summary

This study introduces a new method for converting diols to alkenes using hydrazine as a reductant via HOME chemistry. This sustainable process avoids harsh conditions and minimizes waste for various diol compounds.

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Area of Science:

Organic Chemistry
Catalysis
Green Chemistry

Background:

Deoxydehydration (DODH) of diols to alkenes is a crucial transformation.
Existing methods often require harsh reaction conditions or generate significant waste.

Purpose of the Study:

To develop a novel, efficient, and sustainable method for the deoxydehydration of diols to alkenes.

Main Methods:

Utilized hydrazine as a reductant in a novel HOME (hydrazone as an organometallic equivalent) chemistry approach.
Employed Ru-PNP complexes as catalysts for the deoxydehydration reaction.

Main Results:

Successfully achieved deoxydehydration of diols to alkenes under mild reaction conditions.
Demonstrated the broad applicability of the method across various diol substrates.
The process minimizes waste generation compared to traditional methods.

Conclusions:

The developed Ru-catalyzed HOME chemistry offers a green and efficient alternative for diol deoxydehydration.
This novel method provides a sustainable pathway for alkene synthesis from diols.