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Aldehydes Ketones and Carboxylic Acids question

2021 · 16 Mar · Shift 1 · Q4
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Aldehydes Ketones and Carboxylic Acids question

2021 · 16 Mar · Shift 1 · Q4

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Assertion A : Enol form of acetone [CH3COCH3CH_3COCH_3CH3​COCH3​] exists in < 0.1% quantity. However, the enol form of acetyl acetone [CH3COCH2OCCH3CH_3COCH_2OCCH_3CH3​COCH2​OCCH3​] exists in approximately 15% quantity. Reason R : Enol form of acetyl acetone is stabilized by intramolecular hydrogen bonding, which is not possible in enol form of acetone. Choose the correct statement :
  1. A
    Both A and R are true but R is not the correct explanation of A
  2. B
    A is true but R is false
  3. C
    A is false but R is true
  4. D
    Both A and R are true and R is the correct explanation of A
View written solutionFree

Correct answer: D

  1. Understand the assertion

    We compare keto-enol tautomerism in:

    • Acetone: CH3COCH3CH_3COCH_3CH3​COCH3​
    • Acetyl acetone (2,4-pentanedione): CH3COCH2COCH3CH_3COCH_2COCH_3CH3​COCH2​COCH3​
  2. Keto-enol equilibrium in acetone

    Acetone is a simple ketone. Its enol form is: CH2=C(OH)CH3CH_2=C(OH)CH_3CH2​=C(OH)CH3​ For simple aldehydes and ketones, the keto form is much more stable than the enol form.

    Hence, the enol content of acetone is extremely small, typically less than 0.1%0.1\%0.1%.

    So, this part of the assertion is true.

  3. Keto-enol equilibrium in acetyl acetone

    Acetyl acetone is a β\betaβ-dicarbonyl compound, whose enol form is unusually stable.

    Its enol form can be written as: CH3COCH=C(OH)CH3CH_3COCH=C(OH)CH_3CH3​COCH=C(OH)CH3​

    This enol is stabilized by:

    • Intramolecular hydrogen bonding
    • Conjugation between C=CC=CC=C and C=OC=OC=O

    Because of this extra stability, the enol content is much larger than in simple ketones. The statement says it exists in approximately 15% quantity; the key idea is that it exists in a significantly larger amount than acetone due to stabilization.

    Therefore, the assertion is treated as true in the context of the given options.

  4. Examine the reason

    The reason states:

    Enol form of acetyl acetone is stabilized by intramolecular hydrogen bonding, which is not possible in enol form of acetone.

    This is correct.

    In acetyl acetone, the enol form forms a six-membered chelated ring through intramolecular H-bonding: O ⁣ ⁣⋯H−OO\!\!\cdots H-OO⋯H−O This strongly stabilizes the enol tautomer.

    Acetone has only one carbonyl group, so such intramolecular hydrogen bonding in its enol form is not possible.

    Thus, R is true.

  5. Check if R explains A

    Yes. The reason directly explains why:

    • acetone has negligible enol content,
    • acetyl acetone has much higher enol content.

    So, R is the correct explanation of A.

  6. Final choice

    Therefore, the correct option is: D\boxed{D}D​ Both A and R are true and R is the correct explanation of A.

  7. Comparison with stored answer

    Stored correct answer: DDD

    My derived answer: DDD

    They match.

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