Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the correct order of acidic strength for the indicated hydrogen atoms in the following compounds: (I) (II) (III)
Options
- A(I) > (II) > (III)
- B(II) > (III) > (I)
- C(III) > (I) > (II)
- D(I) > (III) > (II)
Correct answer
B. (II) > (III) > (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. In all three compounds, the carbanion formed is stabilized by resonance with the adjacent carbonyl group. The difference in stability arises from the nature of the aromatic ring attached to the carbanion carbon. 1. In compound (II), the carbanion is attached to the 4-position of the pyridine ring. Through resonance, the negative charge can be delocalized onto the elec