The acidity of α-hydrogens (hydrogens attached to the carbon adjacent to a functional group) depends on the stability of the conjugate base formed after proton removal.
- Ketones: The α-hydrogen in carbonyl compounds like ketones is acidic due to two factors:
- Electron-withdrawing effect (-I): The carbonyl group (>C=O) pulls electron density, weakening the C−H bond.
- Resonance Stabilization: The conjugate base (enolate ion) is stabilised by resonance, where the negative charge is delocalised onto the electronegative oxygen atom.
- Comparison: Alkanes, alkenes, and amines generally have much higher pKa values (lower acidity) because their conjugate bases lack this degree of stabilization. Therefore, a strong base readily abstracts a proton from a ketone compared to the others.