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Question
Chemistry
Posted 10 months ago

Please design the synthetic route of the following transformation
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Answer from Sia
Posted 10 months ago
Solution
1
Identify the target molecule: The target molecule is a dicarboxylic acid with a bicyclic structure consisting of two fused cyclobutane rings. Each cyclobutane ring is represented as a square, and each has a carboxylic acid group (-COOH) attached
2
Consider possible synthetic routes: To synthesize the target molecule, we need to form the bicyclic structure and introduce the carboxylic acid groups. A Diels-Alder reaction can be used to form the bicyclic structure, and oxidation reactions can introduce the carboxylic acid groups
3
Design the Diels-Alder reaction: The Diels-Alder reaction requires a diene and a dienophile. For the bicyclic structure, we can use a diene with two double bonds that can react with a dienophile to form the two fused cyclobutane rings
4
Select appropriate reactants: Formaldehyde (HCHO) can be used as a building block to synthesize the diene and dienophile needed for the Diels-Alder reaction. Acetaldehyde (CH3_3CHO) can be used to introduce the necessary methyl groups
5
Synthesize the diene and dienophile: The diene can be synthesized by a series of reactions starting from formaldehyde, and the dienophile can be synthesized from acetaldehyde
6
Perform the Diels-Alder reaction: React the synthesized diene with the dienophile under appropriate conditions to form the bicyclic structure
7
Oxidize to form carboxylic acids: Once the bicyclic structure is formed, perform oxidation reactions to convert the corresponding groups into carboxylic acid groups (-COOH)
Answer
The synthetic route involves the synthesis of a diene and a dienophile from formaldehyde and acetaldehyde, followed by a Diels-Alder reaction to form the bicyclic structure, and subsequent oxidation to introduce the carboxylic acid groups.
Key Concept
Diels-Alder reaction and subsequent oxidation
Explanation
The Diels-Alder reaction is used to form the bicyclic structure, and oxidation reactions are used to introduce the carboxylic acid groups in the target molecule.

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