The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the. An aldol condensation is a condensation reaction in organic chemistry in which an enol or an Quantitative yields in Claisen–Schmidt reactions have been reported in the absence of solvent using sodium hydroxide as the base and plus . The Claisen Condensation. Claisen condensation of esters. Reaction type: Nucleophilic Acyl Substitution. Summary. The Claisen condensation is the ester.

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The first step is formation of the Transition metal carbene complex 2.

Aldol condensation

Coupling reactions Condensation reactions Carbon-carbon claisen-cshmidt forming reactions Name reactions. Journal of Organic Chemistry. Methyl and ethyl esters, which yields methoxide and ethoxide, respectively, are commonly used. Ethyl glyoxylate 2 and diethyl 2-methylglutaconate 1 react to isoprenetricarboxylic acid 3 isoprene skeleton with sodium ethoxide.

Claisen condensation

It is important to distinguish the aldol condensation from other addition reactions of carbonyl compounds. The reaction between menthone and anisaldehyde is complicated due to steric shielding of the ketone group. Support for the reaction mechanism is based on isotope labeling.

Next, the carbonyl carbon of the other ester is nucleophilically attacked by the enolate anion. Then 2N hydrochloric acid is added and the mixture extracted with diethyl ether. In mixed Claisen condensations, a non-nucleophilic base such as lithium diisopropylamideor LDA, may be used, since only one claisen-svhmidt is enolizable.


However, the aldol reaction is not formally a condensation reaction because it does not involve the loss of a small molecule. Retrieved from ” https: Advanced Organic Chemistry 5th ed.

The base used must not interfere with the reaction by undergoing nucleophilic substitution or addition with a carbonyl carbon. From Wikipedia, the free encyclopedia.

Structure and Mechanisms 3rd ed.

The combined organic layers are washed with 2N hydrochloric acidsaturated sodium bicarbonate and brine. A reaction mechanism that explains the formation of both an ester group and a carboxylic acid group is centered on a lactone intermediate Advanced Organic Chemistry Part A: The alkoxy portion of the ester must be a relatively good leaving group.

This page was last edited on 29 Aprilat Because it is only the cis claisen-schmixt that precipitates from solution, this product is formed exclusively. Dehydration may be accompanied by decarboxylation when an activated carboxyl group is clndensacion.

Aldol condensation – Wikipedia

The aldol addition product can be dehydrated via two mechanisms; a strong base like potassium t -butoxidepotassium hydroxide or sodium hydride in an enolate mechanism, [13] [14] or in an condensaclon enol mechanism.

This page was last edited on 31 Decemberat Journal of the American Chemical Society. The reaction between an aldehyde or ketone having condesnacion alpha-hydrogen with an aromatic carbonyl compound lacking an alpha hydrogen is called the Claisen—Schmidt condensation. This is believed to be due to steric strain resulting from the methyl group and the carboxylic group in the cis -dienoid structure.

The final step is reductive elimination to form the cycloalkene. In other projects Wikimedia Commons.


Due to epimerization through a common enolate ion intermediate A the reaction product has RR – cis -configuration and not RS – trans -configuration as in the starting material. Retrieved from ” https: Berichte der Deutschen Chemischen Gesellschaft. The name aldol condensation is also commonly used, especially in biochemistryto refer to just xe first addition stage of the process—the aldol reaction itself—as catalyzed by aldolases. There are a number of different combinations of enolizable and nonenolizable carbonyl compounds that form a few different types of Claisen.

This reaction product is very unstable with initial loss of carbon dioxide and followed by many secondary reactions.

File:Claisen condensation – Wikimedia Commons

Upper Saddle River, NJ: This obstacle is overcome by using a strong base such as potassium hydroxide and a very polar solvent such as DMSO in the reaction below: Reactions, Mechanisms and Structure 3rd ed.

The Stobbe condensation [5] is a modification specific for the diethyl ester of succinic acid requiring less strong bases. LDA is not commonly used in the classic Claisen or Dieckmann condensations due to enolization of the electrophilic ester.

Schmidtwho independently published on this topic in and Depending on the nature of the desired product, the aldol condensation may be carried out under two broad types of conditions: