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

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Chemistry

Turner Blair

6 May, 15:25

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

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Harrison White · 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.