Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in decreasing order of the acidity of their underlined hydrogen atoms: (I) (II) (III) CH ₃- C C - H
Options
- A(II) > (III) > (I)
- B(I) > (III) > (II)
- C(I) > (II) > (III)
- D(II) > (I) > (III)
Correct answer
C. (I) > (II) > (III)
Step-by-step solution
The acidity of a compound is determined by the stability of its conjugate base. A more stable conjugate base corresponds to a stronger acid. 1. For compound (I), acetic acid ( CH₃COOH ), the removal of the underlined proton yields the acetate ion ( CH₃COO^- ). This conjugate base is highly stabilized by equivalent resonance, where the negative charge is delocalized equally over two highly electronegative oxygen atoms. Its pK_a is approximately 4.76 . 2. For compound (II), 1,3-cyclohexanedione, the removal of the ac