Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the correct order of acidic strength for the indicated hydrogen atom in the following compounds: (I) (II) (III)
Options
- A(I) > (II) > (III)
- B(III) > (II) > (I)
- C(I) > (III) > (II)
- D(III) > (I) > (II)
Correct answer
B. (III) > (II) > (I)
Step-by-step solution
The acidic strength of the indicated hydrogen atom depends on the stability of the conjugate base (carbanion) formed after the removal of the proton ( H^+ ). When the proton is removed from the C2 position, a negative charge is generated on the carbon atom between the two heteroatoms. In compound (I), the carbanion is flanked by two oxygen atoms. Oxygen is highly electronegative and exerts a -I effect, but it lacks vacant d-orbitals. Thus, it cannot stabilize the negative charge through resonance. Additionally, the