Draw the most stable form of the major product in the following reaction.

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Draw the most stable form of the major product in the following reaction.

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Answer 1

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Answer #1

Claisen Condensation:

The claisen condensation is similar to aldol condensation. An ester has alpha hydrogens, which undergo the condensation reaction.

The base that is most commonly used in the claisen condensation reaction is alkoxide, [{ m{R}}{{ m{O}}^{ m{ - }}}{ m{N}}{{ m{a}}^{ m{ + }}}]. The ester, on reaction with base, forms an ester enolate, which again reacts with another molecule of ester.

The enolate is a good nucleophile, and ester carbonyl carbon is electrophilic by nature.

The final product of this reaction is a beta-ketoester.

The overall scheme of claisen condensation is as follows:

The base abstracts the alpha hydrogen of ester, which forms a carbanion. The carbanion donates its electrons to form a highly resonance-stabilized enolate, anion. The enolates are very strong nucleophiles.

Take care to correctly abstract the alpha hydrogen, with respect to the carbonyl group.

Correct answer:

Incorrect answer:

Treat another ester with the enolate anion.

The enolates are very strong nucleophiles, and the carbon of ester carbonyls are very strong electrophiles by nature. Hence, the nucleophilic carbon from the ester enolate, attacks the electrophilic carbonyl carbon, which gives a condensed product.

Indicate the correct electron pushing mechanism. The head of the arrow should point towards the electrophilic site, and the tail of the arrow should point towards the nucleophilic site.

Correct electron pushing mechanism:

Incorrect electron pushing mechanism:

Treat the product with hydronium ion.

The most stable form of the major product in the given reaction is:

The reaction of alkoxide with hydronium ion gives beta-ketoester with alcohol, and water molecules as side products. Ethanol is a solvent that is used in this reaction, which does not involve in the reaction mechanism

The most stable form of the major product in the given reaction is:

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Answer 2

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