In Benzoin Condensation, Carbon-carbon Bond is Formed when Two Molecules of Aldehydes Reacts with each other to Form Benzoin. Learn about Benzoin. Abstract: The benzoin condensation in methanol at ‘ proceeds by addition of cyanide ion to benzaldehyde. (AG* – 12 kcal/mol, AGOzg8 = f Benzoin Condensation Benzoin derivatives are important intermediates for the synthesis of a variety of compounds including deoxybenzoins.

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Benzoin condensation – Wikipedia

The reaction is formally a 1,2-addition reaction and is catalyzed by nucleophiles such as a cyanide anion or an N-heterocyclic carbene usually thiazolium salts. This page was last edited on 21 Decemberat Some aldehydes can only donate protons, such as 4-Dimethylaminobenzaldehyde whereas benzaldehyde is both a proton acceptor and donor. The reaction can be extended to aliphatic aldehydes with base catalysis in the presence of thiazolium salts ; the reaction mechanism is essentially the same Views Read Edit View history.

This coenzyme also contains a thiazolium moiety, which on deprotonation becomes a nucleophilic carbene.

Benzoin Condensation

It acts as a nucleophilefacilitates proton abstraction, and is also the leaving group in the final step. Proton transfer and elimination of the cyanide ion affords benzoin as the product. Since condensaation products of the reaction are thermodynamically controlled, the Retro-Benzoin Condensation can be synthetically useful. From Wikipedia, the free encyclopedia.


In the first step in this reaction, the cyanide anion as sodium cyanide reacts with the aldehyde in a nucleophilic addition. In this reaction, the two aldehydes serve different purposes; one aldehyde donates a proton and one aldehyde accepts a proton. The asymmetric version of benzoins reaction has been performed by utilizing chiral thiazolium and triazolium salts.

Rearrangement condrnsation the intermediate results in polarity reversal of the carbonyl group, which then adds to the second carbonyl group in a second nucleophilic addition. By using this site, you agree to the Terms of Use and Privacy Policy. In this way it is possible to synthesise mixed benzoins, i.

Benzoin Condensation | Benzoin Condensation Reaction Mechanism | [email protected]

The reaction generally occurs between aromatic aldehydes or glyoxals. The cyanide ion serves three different purposes in the course of benzojne reaction.

Journal of the Chemical Society, Transactions.

The reaction mechanism is the same as above, but it occurs in the reverse direction. This can allow the access of ketones otherwise difficult to produce. This is a reversible reactionwhich means that the distribution of products is determined by the relative thermodynamic stability of the products and starting material. The analogous 1,4-addition of an aldehyde to an enone is called the Stetter reaction. The benzoibe product is henzoine aromatic acyloinwith benzoin as the parent compound.


These compounds are important in the synthesis of heterocyclic compounds.

If a benzoin or acyloin can condennsation synthesized by another method, then they can be converted into the component ketones using cyanide or thiazolium catalysts. Cyanohydrins regarded as complex acids”. In biochemistrythe coenzyme thiamine is responsible for biosynthesis of acyloin-like compounds utilizing the benzoin condensation. For this reason the reaction is also called a benzoin addition.

The benzoin condensation is in effect a dimerization and not a condensation because a small molecule like water is not released in this reaction. However, care should be taken to match a proton donating aldehyde with a proton accepting aldehyde to avoid undesired homo-dimerization.

Benzoin condensation

The benzoin condensation is a reaction often called a condensation reactionfor historical reasons between two aldehydesparticularly benzaldehyde. Angewandte Chemie International Edition. Triazolium salts were found to give greater enantiomeric excess than thiazolium salts. Retrieved from ” https: