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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Identify the correct order of acidic strength for the indicated protons in the following compound:

Options

  1. A(i) > (iii) > (ii)
  2. B(iii) > (i) > (ii)
  3. C(i) > (ii) > (iii)
  4. D(ii) > (iii) > (i)

Correct answer

D. (ii) > (iii) > (i)

Step-by-step solution

The acidic strength of a proton is directly proportional to the stability of its conjugate base. Removal of proton (ii) yields the cyclopentadienyl anion. This anion has 6 electrons in a cyclic, continuous conjugated system, making it aromatic and exceptionally stable. Removal of proton (i) yields the cycloheptatrienyl anion. This anion has 8 electrons in a cyclic, continuous conjugated system, making it antiaromatic and highly unstable. Removal of proton (iii) yields a localized tertiary carbanion on the alkyl cha

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