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Which of the following dicarboxylic acid...

Which of the following dicarboxylic acid will give cycle alkanone on heating?

A

B

C

D

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The correct Answer is:
To determine which dicarboxylic acid will yield a cyclic alkanone upon heating, we can analyze the structure of each dicarboxylic acid and the mechanism of cyclization that occurs during heating. Let's go through the steps systematically. ### Step-by-Step Solution: 1. **Understanding Dicarboxylic Acids**: Dicarboxylic acids contain two carboxylic acid (-COOH) groups. When heated, they can undergo decarboxylation, which involves the loss of carbon dioxide (CO2) and can lead to the formation of cyclic compounds. 2. **Identifying the Structure**: For each option provided, we need to draw the structure of the dicarboxylic acid. This will help us visualize the potential for cyclization. 3. **Heating and Decarboxylation**: Upon heating, one of the carboxylic acid groups will lose CO2. The remaining carboxylate ion can then attack the carbonyl carbon of the other carboxylic acid group, leading to the formation of a cyclic compound. 4. **Cyclization Mechanism**: - **Alpha and Beta Position**: Identify the alpha (the carbon adjacent to the carboxylic group) and beta positions (the next carbon) in the molecule. The carbanion formed at the alpha position will attack the carbonyl carbon of the other carboxylic acid group. - **Ring Formation**: Depending on the number of carbons involved in the cyclization, we can predict the size of the ring formed (3-membered, 4-membered, 5-membered, or 6-membered). 5. **Evaluating Each Option**: - **Option 1**: Heating leads to the formation of a 5-membered ring (cyclopentanone). - **Option 2**: Heating leads to the formation of a 6-membered ring (cyclohexanone). - **Option 3**: Heating leads to a 4-membered ring, which is less stable and not preferred. - **Option 4**: Heating leads to a 3-membered ring, which is also unstable due to angle strain. 6. **Conclusion**: The dicarboxylic acids that can form stable cyclic alkanones upon heating are those that can form 5-membered or 6-membered rings. Among the options, the first and second options yield cyclopentanone and cyclohexanone, respectively. However, the formation of cyclopentanone is more favorable. ### Final Answer: The dicarboxylic acid that will give a cyclic alkanone upon heating is **Option 1**, which forms cyclopentanone.
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