See image — GOC and Organic Chemistry Basics Chemistry Question
Question
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💡 Solution & Explanation
**Analysis using Resonance Arguments:** **Identify the three acidic hydrogens:** - $H_a$: attached to oxygen in enol form (top) - $H_b$: attached to oxygen in enol form (left) - $H_c$: attached to oxygen in enol form (bottom right) **Key insight:** Acidity increases when the conjugate base is stabilized by resonance delocalization of negative charge. **For $H_a$ (top position):** When deprotonated, the resulting anion's negative charge can delocalize onto the carbonyl oxygen (strong $C=O$ electron-withdrawing group directly conjugated). This provides significant resonance stabilization. **For $H_b$ (left position):** The conjugate base can delocalize charge, but the carbonyl is farther away and less directly conjugated to the deprotonation site. **For $H_c$ (bottom right position):** The conjugate base has minimal resonance stabilization from the carbonyl group due to its position on the ring, furthest from direct conjugation with electron-withdrawing groups. **Stability order of conjugate bases:** $H_c^-$ (least stabilized) $< H_b^-$ $< H_a^-$ (most stabilized) **Therefore, acidity order:** $$H_c < H_a < H_b$$ **Answer: (A)** $H_c < H_a < H_b$ ✓ The most acidic hydrogen is the one whose conjugate base is most stabilized by resonance with the carbonyl group.