Other conceivable products of the Claisen condensation of ethyl acetate are and Explain how these products might be formed and why they are not formed in significant amounts.

Short Answer

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The other conceivable products of the Claisen condensation of ethyl acetate are ethyl 3-oxobutanoate, formed from an intramolecular reaction, and diethyl oxalate, formed from a different intermolecular reaction. These products are not formed in significant amounts because the intramolecular reaction has a lower probability of occurring and the formation of diethyl oxalate requires unfavorable conditions. Instead, the preferred intermolecular Claisen condensation pathway is more likely and kinetically favored to occur.

Step by step solution

01

Recap the Claisen condensation

End The Claisen condensation is a nucleophilic acyl substitution reaction involving two esters or an ester and a carbonyl compound in the presence of a base. In this case, we are considering the reaction of ethyl acetate. The reaction involves the deprotonation of the α-hydrogen of an ester by a strong base, followed by the nucleophilic attack of the enolate ion on the ester carbonyl group, and finally the protonation of the alkoxide ion, forming a β-keto ester product.
02

Other conceivable products

Other conceivable products of the Claisen condensation of ethyl acetate could be: 1. Ethyl 3-oxobutanoate (a result of intramolecular reaction) 2. Diethyl oxalate (a result of intermolecular reaction) These products might be formed if the enolate ion, generated after deprotonation, reacts in different ways than intended in the Claisen condensation reaction. Ethyl 3-oxobutanoate could be formed if the enolate ion attacks the carbonyl group of the same ethyl acetate molecule (intramolecular reaction) instead of another ester molecule. Diethyl oxalate could be formed if two ethyl acetate molecules react with each other in an intermolecular reaction.
03

Reasons for not forming in significant amounts

Although these other conceivable products are theoretically possible, they are not formed in significant amounts due to the following reasons: 1. Ethyl 3-oxobutanoate: The intramolecular reaction has a lower probability of occurring compared to the desired intermolecular Claisen condensation, because the enolate ion must rotate to approach the carbonyl group of the same molecule, which would happen with difficulty in comparison to an intermolecular reaction where the enolate ion is free to attack the carbonyl group of another ester molecule. 2. Diethyl oxalate: The formation of diethyl oxalate requires two ethyl acetate molecules to both be deprotonated and their enolate ions to act as nucleophiles and electrophiles simultaneously, which is less likely because there is typically only enough base present to deprotonate a single molecule. Moreover, the Claisen condensation product is kinetically favored as it takes less energy for the carbonyl group of one ester to be attacked by the enolate ion of another ester as opposed to ester groups reacting with each other. In conclusion, these additional conceivable products of the Claisen condensation of ethyl acetate might be formed through intramolecular and different intermolecular reactions, but they are not formed in significant amounts because the preferred intermolecular Claisen condensation pathway is more likely and kinetically favored to occur.

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