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Question: Answered & Verified by Expert
Assertion (A) : pKa of phenol is 4.19 and that of benzoic acid is 10
Reason (R) : Phenoxide ion is stabilised by nonequivalent resonance structures whereas benzoate ion by two equivalent resonance structures
The correct option among the following is
ChemistryGeneral Organic ChemistryTS EAMCETTS EAMCET 2023 (13 May Shift 2)
Options:
  • A A and R are true. R is the correct explanation of $\mathrm{A}$
  • B A and $\mathrm{R}$ are true, but $\mathrm{R}$ is not the correct explanation for $A$
  • C $\mathrm{A}$ is true $\mathrm{R}$ is false
  • D A is false but R is true
Solution:
2520 Upvotes Verified Answer
The correct answer is: A is false but R is true
$\mathrm{pK}_{\mathrm{a}}=-\log \mathrm{K}_{\mathrm{a}}$ so as $\mathrm{K}_{\mathrm{a}}$ increases, $\mathrm{pK}_{\mathrm{a}}$ decreases. Benzoic acid is a stronger acid than phenol so its $\mathrm{pK}_{\mathrm{a}}$ will be smaller than that of phenol.
Thus, Assertion (A) is false.
The resonance structures of phenoxide ion and benzoate ion are given by:-



Thus, Reason (R) is true.

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