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What type of reaction is the intramolecular Claisen condensation?
What type of reaction is the intramolecular Claisen condensation?
The aldol reaction involves the reaction of two different molecules.
The aldol reaction involves the reaction of two different molecules.
True
What is the role of a base in the intramolecular Claisen condensation reaction?
What is the role of a base in the intramolecular Claisen condensation reaction?
to remove a proton from the α-carbon of the ester group, forming an enolate intermediate
The intramolecular Claisen condensation reaction is often used to form _______________________ compounds.
The intramolecular Claisen condensation reaction is often used to form _______________________ compounds.
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What is the product of the intramolecular Claisen condensation reaction?
What is the product of the intramolecular Claisen condensation reaction?
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Match the following compounds with their formation reactions:
Match the following compounds with their formation reactions:
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The reaction mechanism of the intramolecular Claisen condensation reaction involves the formation of a tetrahedral intermediate.
The reaction mechanism of the intramolecular Claisen condensation reaction involves the formation of a tetrahedral intermediate.
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What is the final step in the reaction mechanism of the intramolecular Claisen condensation reaction?
What is the final step in the reaction mechanism of the intramolecular Claisen condensation reaction?
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Study Notes
Mechanism
- The intramolecular Claisen condensation reaction is a type of condensation reaction that occurs within a single molecule.
- It involves the reaction of two ester groups or an ester and a ketone group to form a β-keto ester or β-diketone.
- The reaction is facilitated by a base, such as sodium ethoxide or sodium hydride, which removes a proton from the α-carbon of the ester group, forming an enolate intermediate.
Aldol Reaction
- The intramolecular Claisen condensation reaction is similar to the aldol reaction, but it occurs within a single molecule.
- The key difference is that the aldol reaction involves the reaction of two different molecules, whereas the Claisen condensation reaction occurs within a single molecule.
- Both reactions involve the formation of a β-hydroxy carbonyl compound, but the Claisen condensation reaction forms a ring instead of a linear product.
Cyclic Compounds
- The intramolecular Claisen condensation reaction is often used to form cyclic compounds, such as β-keto esters or β-diketones.
- The reaction is particularly useful for forming five- or six-membered rings, which are common in natural products and pharmaceuticals.
- The cyclic compounds formed through the Claisen condensation reaction can be further modified through additional reactions, such as alkylation or reduction.
Reaction Mechanism
- The reaction mechanism involves the following steps:
- Deprotonation of the α-carbon of the ester group to form an enolate intermediate.
- Nucleophilic attack of the enolate intermediate on the carbonyl group of the other ester or ketone.
- Formation of a tetrahedral intermediate, which then collapses to form a β-keto ester or β-diketone.
- Tautomerization of the β-keto ester or β-diketone to form the final product.
Note: The reaction mechanism may vary depending on the specific reactants and conditions used.
Mechanism
- Intramolecular Claisen condensation reaction is a type of condensation reaction occurring within a single molecule, involving the reaction of two ester groups or an ester and a ketone group to form a β-keto ester or β-diketone.
- Base facilitation is required, such as sodium ethoxide or sodium hydride, which removes a proton from the α-carbon of the ester group, forming an enolate intermediate.
Comparison with Aldol Reaction
- Intramolecular Claisen condensation reaction is similar to the aldol reaction, but occurs within a single molecule, whereas the aldol reaction involves the reaction of two different molecules.
- Both reactions involve the formation of a β-hydroxy carbonyl compound, but the Claisen condensation reaction forms a ring instead of a linear product.
Applications
- The reaction is often used to form cyclic compounds, such as β-keto esters or β-diketones.
- It is particularly useful for forming five- or six-membered rings, common in natural products and pharmaceuticals.
- Cyclic compounds formed through the Claisen condensation reaction can be further modified through additional reactions, such as alkylation or reduction.
Reaction Mechanism
- Deprotonation of the α-carbon of the ester group to form an enolate intermediate.
- Nucleophilic attack of the enolate intermediate on the carbonyl group of the other ester or ketone.
- Formation of a tetrahedral intermediate, which then collapses to form a β-keto ester or β-diketone.
- Tautomerization of the β-keto ester or β-diketone to form the final product.
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Description
This quiz covers the intramolecular Claisen condensation reaction and the Aldol reaction in organic chemistry, including the reaction mechanisms and conditions.
