The correct order of the pKa of the following compounds is

F2 Madhuri Teaching 10.01.2023 D9

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  1. C > B > A
  2. A > C > B
  3. B > A > C
  4. A > B > C

Answer (Detailed Solution Below)

Option 2 : A > C > B
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Detailed Solution

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Concept:

Acid Strength and Aromatacity:

  • A substance that gives H+ ion in the solution and forms salts by combining with some metals is called acid. According to Arrhenius, acid is a substance that releases an H+ ion in the solution and a base is a substance that accepts an H+ ion from the solution.
  • The pKa value indicates the strength of an acid in the solution. The lower the value of pKa, the more the acid's strength will be.
  • Aromatic compounds follow Huckel's rule, according to which a cyclic, planar, and conjugated species having (4n+2)pi electrons (n = 0,1,3...) is aromatic.
  • Aromatic compounds are very stable.
  • Whereas, the anti-aromatic compounds follow the 4npi electrons rule. According to this a cyclic, planar, and conjugated species having (4n+2)pi electrons (n = 0,1,3...) is aromatic.
  • Anti-aromatic compounds are very unstable.

Explanation:

  • The conjugate base formed by compound A after deprotonation is an anti-aromatic compound with 4npi electrons for n=1, which is unstableThus, compound A has lower acid strength and a high value of pKa.
  • The conjugate base formed by compound C after deprotonation is an anti-aromatic compound with 8npi electrons for n=2, which is unstable. Thus, compound B also has a lower acid strength and a high pKa value.
  • The conjugate base formed by compound B after deprotonation is an aromatic compound with 6npi electrons for n=1, which is very stable. Thus, compound B has the highest acid strength and lowest value of pKa.

F2 Madhuri Teaching 10.01.2023 D10

Conclusion:

  • Thus, the correct order of the pKof the following compounds is A > C > B.
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