Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Identify the correct decreasing order of acidity for the indicated hydrogen atoms ( H ₁ , H ₂ , and H ₃ ) in the following compound:
Options
- AH ₁ > H ₂ > H ₃
- BH ₃ > H ₂ > H ₁
- CH ₁ > H ₃ > H ₂
- DH ₂ > H ₁ > H ₃
Correct answer
A. H ₁ > H ₂ > H ₃
Step-by-step solution
The acidity of a hydrogen atom depends on the stability of its corresponding conjugate base (carbanion). A more stable conjugate base implies a more acidic proton. Let us analyze the conjugate bases formed by the removal of each indicated proton: 1. Removal of H ₁ : The proton H ₁ is attached to the C-2 carbon, which is flanked by two carbonyl ( > C=O ) groups. This is an active methylene position. The resulting carbanion is highly stabilized by resonance ( -M effect) with both adjacent carbonyl oxygen atoms. This