Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in decreasing order of the acidity of their most acidic hydrogen atom: (I) (II) (III) CH ₃ COOH
Options
- A(II) > (III) > (I)
- B(I) > (III) > (II)
- C(III) > (II) > (I)
- D(III) > (I) > (II)
Correct answer
C. (III) > (II) > (I)
Step-by-step solution
The acidic strength of a compound is directly proportional to the stability of its conjugate base. In compound (III), acetic acid ( CH₃COOH ), the conjugate base is the acetate ion ( CH₃COO^- ). It is highly stabilized by two equivalent resonance structures, distributing the negative charge equally over two electronegative oxygen atoms. This makes it the most acidic among the given compounds. In compound (II), acetylacetone ( CH₃COCH₂COCH₃ ), the most acidic hydrogen is located on the active methylene group between