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Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry

Identify the correct decreasing order of acidic strength for the indicated protons in the following compounds: (i) (ii) (iii)

Options

  1. Aiii > i > ii
  2. Bi > iii > ii
  3. Cii > i > iii
  4. Dii > iii > i

Correct answer

A. iii > i > ii

Step-by-step solution

Let us analyze the given compounds and the stability of their conjugate bases: Compound (i) is cyclopentane-1,3-dione. The indicated proton is an active methylene proton flanked by two ketone carbonyl groups. Its conjugate base is a highly stable enolate delocalized over two oxygen atoms. The pKa of cyclopentane-1,3-dione is approximately 4.5 . Compound (ii) is succinimide. The indicated proton is on the nitrogen atom. Its conjugate base is stabilized by delocalization over two carbonyl groups. However, the N-H pro

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