Questions: Question 5 Which of the following structures is NOT a tautomer of the structure shown below?

Question 5 Which of the following structures is NOT a tautomer of the structure shown below?
Transcript text: Question 5 Which of the following structures is NOT a tautomer of the structure shown below?
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Solution

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Solution Steps

Step 1: Identify the given structure

The given structure is a β-ketoester. It can undergo tautomerization.

Step 2: Keto-Enol Tautomerism

The most common tautomerism is keto-enol tautomerism. The given structure can form an enol by shifting a hydrogen from the carbon next to the ketone carbonyl to the carbonyl oxygen, forming a double bond between the alpha carbon and the carbonyl carbon. This can happen on either side of the ketone carbonyl.

Step 3: Enol Tautomerization to other carbonyls

The enol form can also tautomerize to form an ester enol by shifting the double bond.

Step 4: Analyze the Options

All options shown are tautomers of the initial structure, formed via keto-enol tautomerism, except for option (D). Option (D) has a different connectivity of atoms and is thus not a tautomer.

Final Answer

D

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