Question

The protons on C3 of pentane-2,4-dione have a pKa of approximately 10. Using curved arrows, propose a mechanism for the acid-base reaction equation shown below, including an contributing resonance structures that account for the increased acidity of these protons. KOH H entane-2,4-dione pKa 10

Answer 1

Explanation has been given below.

Step-by-step explanation:

• Protons on C-3 atom are highly acidic due to high stability of the corresponding conjugate base.
• Stability of conjugate base arises due to presence of two adjacent keto groups
• Negative charge on C-3 atom in conjugate base can delocalize through resonance into two adjacent keto groups which renders stability of the conjugate base.
• Mechanism of the acid-base reaction as well as contributing resonance structures of conjugate acid has been shown below.