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The most stable enolic form of 2, 4-pent...

The most stable enolic form of 2, 4-pentanedione is :

A

`CH_(2)=overset(OH) overset(|)(CH)-CH_(2)- overset(O) overset(||)(C)-CH_(3)`

B

`CH_(3)=overset(OH) overset(|)(C)=CH- overset(O) overset(||)(C)-CH_(3)`

C

`CH_(2)=underset(OH) underset(|)(CH)-CH_(2)- underset(O) underset(||)(C)-CH_(3)`

D

`CH_(3)=underset(OH) underset(|)(C)= C = underset (OH) underset(|)(C)-CH_(3)`

Text Solution

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The correct Answer is:
To determine the most stable enolic form of 2,4-pentanedione, we can follow these steps: ### Step 1: Understand the Structure of 2,4-Pentanedione 2,4-Pentanedione (also known as acetylacetone) has the following structure: - It contains two carbonyl (C=O) groups at positions 2 and 4 of a five-carbon chain. - The molecular formula is C5H8O2. ### Step 2: Identify the Enolic Form The enolic form of a diketone like 2,4-pentanedione is formed by the deprotonation of one of the alpha hydrogens adjacent to the carbonyl group, leading to the formation of a double bond between the carbon and the carbon bearing the hydroxyl group (OH). ### Step 3: Analyze the Stability Factors The stability of the enolic form can be influenced by: - **Hydrogen bonding**: Intramolecular hydrogen bonding can significantly stabilize the enolic form. - **Number of alpha hydrogens**: More alpha hydrogens can lead to more possible tautomeric forms, but the presence of hydrogen bonding is a more critical factor for stability. ### Step 4: Draw Possible Enolic Structures 1. **Option 1**: Enol form with intramolecular hydrogen bonding. 2. **Option 2**: Enol form without significant hydrogen bonding. 3. **Option 3**: Another enolic form with different positioning of the double bond and hydroxyl group. ### Step 5: Compare Stability - The enolic form with intramolecular hydrogen bonding is typically the most stable due to the stabilization provided by the hydrogen bond. - The other enolic forms may lack this stabilizing interaction, making them less stable. ### Conclusion The most stable enolic form of 2,4-pentanedione is the one that features intramolecular hydrogen bonding, which is typically the second option presented in the question. ---

To determine the most stable enolic form of 2,4-pentanedione, we can follow these steps: ### Step 1: Understand the Structure of 2,4-Pentanedione 2,4-Pentanedione (also known as acetylacetone) has the following structure: - It contains two carbonyl (C=O) groups at positions 2 and 4 of a five-carbon chain. - The molecular formula is C5H8O2. ### Step 2: Identify the Enolic Form ...
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