Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in decreasing order of the acidity of the indicated hydrogen atom (H): (i) (ii) (iii)
Options
- A(i) > (iii) > (ii)
- B(iii) > (i) > (ii)
- C(i) > (ii) > (iii)
- D(ii) > (iii) > (i)
Correct answer
C. (i) > (ii) > (iii)
Step-by-step solution
The acidity of a hydrogen atom is directly proportional to the stability of its conjugate base formed after the removal of a proton ( H^+ ). 1. For compound (i) (cyclopentadiene), the removal of H^+ yields the cyclopentadienyl anion. This anion is cyclic, planar, fully conjugated, and has 6 electrons. It satisfies Huckel's rule ( 4n+2 electrons, where n=1 ), making it aromatic. This aromaticity provides exceptional stability to the conjugate base. 2. For compound (ii) (cycloheptane), the removal of H^+ yields the c