Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the correct decreasing order of acidity for the indicated hydrogen atoms in the following molecules: (I) (II) (III)
Options
- A(I) > (II) > (III)
- B(II) > (III) > (I)
- C(I) > (III) > (II)
- D(III) > (I) > (II)
Correct answer
D. (III) > (I) > (II)
Step-by-step solution
The acidity of a hydrogen atom depends on the stability of its conjugate base. In molecule (III), the indicated hydrogen is attached to an electronegative oxygen atom ( O-H bond). Its removal forms the acetate ion ( CH₃COO^- ), which is highly stabilized by equivalent resonance structures over two oxygen atoms. Thus, it is the most acidic among the three. In molecules (I) and (II), the indicated hydrogens are attached to carbon atoms ( -hydrogens). The acidity of these C-H bonds depends on the electron-withdrawing