A stepwise mechanism for the reaction will be shown by clicking the "Reaction Mechanism" button. J. Org. The Claisen condensation between a ketone and a thionoester has been widely employed for the synthesis of β-oxo thioketones (Equation (39)).Sodamide is commonly used as the base, and the reaction has proved to be applicable to aryl methyl ketones and some aliphatic ketones < 77JCS(P1)1127, 77JOC3123, 77S256 >. Claisen Condensation Practice Problems In the previous post, we talked about the Claisen condensation reaction and went over the mechanism as well as some details regarding the importance of at least two α … Ges.. 1887, 20, 651.
Both the aldol reaction and condensation are reversible. Complete the reaction mechanism for the following Claisen condensation of methyl 3-methylbutanoate in sodium methoxide Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the grid and connecting them with bonds, including charges where needed. In a mixed Claisen condensation (or crossed Claisen condensation), an ester enolate or ketone enolate is condensed with an ester that cannot form an enolate. In fact these are used much more frequently than the classical ester plus ester enolate version. Complete the mechanism for the following mixed Claisen condensation, in which ethyl propanoate is added dropwise to a solution of ethyl benzoate and ethoxide base, by adding any missing atoms, bonds, charges, nonbonding electrons, and curved arrows.
Analogous to the Aldol reaction, the Claisen condensation is a reaction between the alpha carbon of one molecule with the carbonyl group of another molecule.
Mechanism of the Claisen Condensation. The classical Claisen condensation involves the reaction of an ester with an ester enolate to form a β-keto ester. When an enolate forms from an aldehyde, the enolate will normally react with unreacted aldehyde to undergo the "aldol addition" or "aldol condensation" reaction. The Dieckmann condensation is an organic reaction used to form a carbon-carbon bond between two tethered ester groups using an alkoxide base in alcohol to make a cyclic β-keto ester. Generally, the Claisen condensation refers to condensation reactions using esters. E.g. Chem. Since ketones are less reactive toward nucleophilic addition, the enolate formed from a ketone can be used to react with an aldehyde, a modification called the Claisen-Schmidt reaction. Overall, one ester loses an a-hydrogen and the other ester loses the alkoxide group: Mechanism This reaction is essentially an intramolecular form of the Claisen condensation .
Chem.. 2014, 79, 6868. Add two curved arrows. Original publication: Ber. Note the resonance arrow between panels two and three. The aliphatic Claisen Rearrangement is a [3,3]-sigmatropic rearrangement in which an allyl vinyl ether is converted thermally to an unsaturated carbonyl compound.
Dtsch. Aldol reaction with two same aldehyde molecules. The aromatic Claisen Rearrangement is accompanied by a rearomatization: Base-promoted Claisen condensation of methyl acetate gives methyl acetoacetate, a β-keto ester (as a mixture of keto and enol tautomers).