Why is CH3ONa not used in Claisen condensation of ethyl acetate?

Why is CH3ONa not used in Claisen condensation of ethyl acetate?

Why is CH3ONa not used in the Claisen condensation of ethyl acetate? a. CH30 is a weaker base than the CH3CH20-which is used.

What is the name reaction of conversion of ethyl acetate into Aceto acetic ester which condensation?

Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis.

What is the product of the Claisen condensation?

beta-keto ester
The product of a Claisen condensation is a beta-keto ester, which is a significantly stronger acid (pKa = 11) than either alcohols (pKa = 16-17) or esters (pKa = 25).

Which base is commonly used in Claisen condensation reaction?

sodium ethoxide
The Claisen Condensation between esters containing α-hydrogens, promoted by a base such as sodium ethoxide, affords β-ketoesters.

How is ethyl acetoacetate synthesized using Claisen condensation?

Condensation Reactions of Carbonyl Compounds The Claisen condensation of ethyl acetate yields ethyl acetoacetate. This readily available compound and other β-keto esters formed by Claisen condensations are used as intermediates in the synthesis of alkyl derivatives of ketones.

What is Claisen condensation and discuss its mechanism?

The Claisen condensation reaction is an organic coupling reaction that results in the formation of a C-C bond between either a single ester and one carbonyl compound or between two esters. The reaction proceeds when a strong base is present and the product of the reaction is a beta-keto ester or a beta-diketone.

What intermediate is in Claisen condensation?

In the ‘main’ part of the Claisen condensation mechanism, the α-carbon of a second acetyl CoA is deprotonated (step 1), forming a nucleophilic enolate. The enolate carbon attacks the electrophilic thioester carbon, forming a tetrahedral intermediate (step 2) which collapses to expel the cysteine thiol (step 3).

Which catalyst is used in Claisen condensation?

Although many Claisen condensations are carried out with a full equivalent of the alkoxide base, an effective alternative procedure, used in reaction #5, uses sodium hydride (NaH) together with a catalytic amount of alcohol.

Which compound can be prepared by a mixed Claisen condensation?

A beta-keto ester or a beta-aldo ester could possibly be made by a Claisen condensation of two esters. A beta-dicarbonyl could possibly be made by a Claisen-like condensation between a ketone and an ester.

What type of reaction is a Claisen condensation?

The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base, resulting in a β-keto ester or a β-diketone.

What is Claisen condensation?

What is Claisen Condensation? The Claisen condensation reaction is an organic coupling reaction that results in the formation of a C-C bond between either a single ester and one carbonyl compound or between two esters. The reaction proceeds when a strong base is present and the product of the reaction is a beta-keto ester or a beta-diketone.

How to cross Claisen esters?

The second possibility for doing crossed Claisen is the use of LDA as a strong, sterically hindered base to irreversibly deprotonate one of the esters. This approach allows to selectively convert one of the esters into an enolate and keep the other one as is to serve as the electrophile:

Why is ethyl formate used in Crossed Claisen reactions?

Ethyl formate is especially suitable for crossed Claisen reactions since, in addition to not having an ɑ hydrogen, it also resembles an aldehyde which are more reactive as electrophiles toward enolates:

What is the difference between aldol condensation and Claisen condensation?

However, the aldol condensation reaction involves the addition of enolates to ketones or aldehydes whereas Claisen condensation involves the addition of enolates to esters. What are the key requirements for the Claisen condensation reaction? The Claisen condensation reaction requires at least one of the reagents used to be enolizable.