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Alcohols Phenols and Ethers question

2023 · 12 Apr · Shift 1 · Q8
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Alcohols Phenols and Ethers question

2023 · 12 Apr · Shift 1 · Q8

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Correct statements for the given reaction are : JEE Main 2023 (Online) 12th April Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 42 English A. Compound 'B\mathrm{B}B' is aromatic B. The completion of above reaction is very slow C. 'A' shows tautomerism D. The bond lengths of C−CC-CC−C in compound BBB are found to be same Choose the correct answer from the options given below:
  1. A
    B, C and D only
  2. B
    A, C and D only
  3. C
    A, B and D only
  4. D
    A, B and C only
View written solutionFree

Correct answer: B

  1. The reaction referred to in this standard question is the keto–enol tautomerism of cyclohexane-1,3,5-trione (or a related tricarbonyl compound) giving benzene-1,3,5-triol as product.

    So we identify:

    • Compound AAA = keto form
    • Compound BBB = enolized aromatic form
  2. Now evaluate each statement.


Statement A: Compound BBB is aromatic

Compound BBB is the fully enolized form with a benzene ring framework. It has a planar cyclic conjugated system with 6π6\pi6π electrons. Hence, by Hückel's rule, 4n+2=6(n=1)4n+2 = 6 \quad (n=1)4n+2=6(n=1) So BBB is aromatic.

✅ A is correct.


Statement B: The completion of above reaction is very slow

Conversion of the keto form to the aromatic enol form is actually highly favored, because the product gains aromatic stabilization. Therefore, this tautomerization is not expected to be very slow in completion; rather, the aromatic form is strongly stabilized.

❌ B is incorrect.


Statement C: AAA shows tautomerism

Compound AAA contains carbonyl groups with adjacent α\alphaα-hydrogen(s), so it can undergo keto–enol tautomerism. Hence AAA shows tautomerism.

✅ C is correct.


Statement D: The bond lengths of C−C\mathrm{C-C}C−C in compound BBB are found to be same

Since BBB is aromatic, the carbon–carbon bonds in the ring are delocalized. Therefore, all the C−C\mathrm{C-C}C−C bond lengths become equal, intermediate between single and double bond lengths.

✅ D is correct.


  1. Therefore, the correct statements are: A, C, D onlyA,\ C,\ D \text{ only}A, C, D only

So the correct option is: B\boxed{\text{B}}B​

  1. Comparison with stored answer:
  • Derived answer: B
  • Stored correct answer: B

They match.

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