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Question

The total number of tautomers for the following molecule (including the structure provided below) is ____________

The molecule provided is a diketone derived from benzene, which can exhibit tautomerism. Tautomerism involves the transfer of a proton, typically resulting in keto-enol transformations.

1. Identify the Keto Groups: The molecule has two carbonyl (C=O) groups. These groups are present in positions amenable to tautomerism.

2. Enol Forms: Each keto group can tautomerize to form an enol. However, due to the structure's nature, each keto-enol transformation can coexist:

  • Keto Form: The original structure as shown.
  • First Enol Form: One keto group converts to enol, forming a hydroxyl group bonded to a carbon involved in a C=C bond adjacent to one of the original carbonyl groups.
  • Second Enol Form: The other keto group tautomerizes similarly, yielding another distinct enol form.

3. Counting Tautomers: Overall, the molecule has three tautomers (including both enol forms and the original keto form).

Thus, the total number of tautomers is 3, which fits the given range (3,3).

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Important Questions from Organic Structure Stability

  1. The reactants P and Q in the following reaction are 

  2. The Diels-Alder adduct from the reaction between cyclopentadiene and benzyne is
  3. The major product from the following reaction is

  4. The order of resonance energy for the following molecules is

  5. The compound, which upon mono-nitration using a mixture of HNO$_3$ and H$_2$SO$_4$, does NOT give the meta-isomer as the major product, is

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