Sodium carbonate is an atypically weak base to use in an aldol condensation reac

Question

Sodium carbonate is an atypically weak base to use in an aldol condensation reaction. In the reaction you performed in lab, the increased acidity of 2-acctylpyridinc (pK_a in DMSO = 23.6) relative to acetophenone (pKa in DMSO = 24.7) allows for the use of a weaker base. Under the same reaction conditions, acetophenone produced a negligible amount of condensation product. Explain the increased acidity of 2-acctylpyridinc compared to acetophenone, making reference to the resonance structures of each species in your answer. You may wish to perform an optional NBO calculation on the optimized geometries of the enolates of 2-acetylpyridine and acetophenone to guide your answer.

Explanation / Answer

it is by considering resonance of benzene vs pyridine. Benzene resonance has no charges in the ring, but pyridine has. the lone pair on the nitrogen provides more resonance stability than without it. finally electronegativity of nitrogen also makes the ring to electron defeicent which increases the acidity of acetyl pyridine.

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