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Cinnamaldehyde can form two enolate ions depending on which hydrogen is removed.
1. α-Enolate: Removal of the hydrogen on the α-carbon (adjacent to the carbonyl group) results in a resonance-stabilized enolate ion.
2. γ-Enolate: Removal of the hydrogen on the γ-carbon (two carbons away from the carbonyl group) forms a less stable enolate due to the conjugated pi-system.
Both enolates can participate in reactions like aldol condensation and Michael addition.