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The most stabl enol tautomer of MeCOC...

The most stabl enol tautomer of `MeCOCH_(2)CO_(2)Et` is

A

`CH_(2)=C (OH)CH_(2)CO_(2)Et`

B

`MeC(OH)=CHCO_(2)Et`

C

`MeCOCH=C(OH)OEt`

D

`CH_(2)=C(OH)CH=C(OH)Et`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the most stable enol tautomer of the compound `MeCOCH2CO2Et` (ethyl acetoacetate), we will follow these steps: ### Step 1: Identify the Keto Form The given compound is ethyl acetoacetate, which can be represented as: \[ \text{CH}_3\text{C(=O)CH}_2\text{CO}_2\text{Et} \] This is the keto form of the compound. ### Step 2: Draw the Enol Form The enol form is obtained by the deprotonation of the alpha hydrogen (the hydrogen on the carbon adjacent to the carbonyl group) and the formation of a double bond between the alpha carbon and the carbonyl carbon. The enol form can be represented as: \[ \text{CH}_3\text{C(=C(OH))CH}_2\text{CO}_2\text{Et} \] ### Step 3: Analyze the Stability of the Enol Form The stability of the enol form can be influenced by several factors: - **Hydrogen Bonding**: The enol can form intramolecular hydrogen bonds, which can stabilize the structure. - **Resonance**: The enol can exhibit resonance stabilization due to the presence of the hydroxyl group. ### Step 4: Compare the Stability of Keto and Enol Forms In general, keto forms are more stable than enol forms due to the presence of a carbonyl group. However, in some cases, the enol form can be stabilized by hydrogen bonding or resonance. ### Step 5: Conclusion For ethyl acetoacetate, the enol tautomer is stabilized by intramolecular hydrogen bonding and resonance. Thus, the most stable enol tautomer of `MeCOCH2CO2Et` is: \[ \text{CH}_3\text{C(=C(OH))CH}_2\text{CO}_2\text{Et} \]

To determine the most stable enol tautomer of the compound `MeCOCH2CO2Et` (ethyl acetoacetate), we will follow these steps: ### Step 1: Identify the Keto Form The given compound is ethyl acetoacetate, which can be represented as: \[ \text{CH}_3\text{C(=O)CH}_2\text{CO}_2\text{Et} \] This is the keto form of the compound. ### Step 2: Draw the Enol Form ...
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