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

Question

Drake Mcintosh

Chemistry

18 September, 23:16

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

+5

Answers (1)

Know the Answer?

Emmett Warren · Answer 1

Explanation has been given below.

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.