Aldehydes & Ketones
⚖️ The Carbonyl Group
Both aldehydes (R-CHO) and ketones (R-CO-R') contain a C=O carbonyl group. The carbon is electron-poor (partially positive) because oxygen is more electronegative, which makes the carbonyl carbon the target of nucleophilic attack.
→ Nucleophilic Addition
A nucleophile attacks the electrophilic carbonyl carbon, breaking the π bond and pushing electrons onto oxygen, which then picks up a proton. This is the core reaction type for both aldehydes and ketones.
🔄 Aldol Condensation
Occurs when a carbonyl compound with an α-hydrogen is treated with a dilute base. The base removes an α-hydrogen to form an enolate, which then attacks the carbonyl carbon of a second molecule, producing a β-hydroxy aldehyde/ketone (an "aldol"). This can lose water on heating to form an α,β-unsaturated carbonyl compound.
⚖️ Cannizzaro Reaction
Occurs with aldehydes that have no α-hydrogen (e.g. benzaldehyde, formaldehyde), when treated with a strong (concentrated) base. Since there's no α-H to remove, the aldehyde instead undergoes a disproportionation: one molecule is oxidized to a carboxylate ion while another is reduced to an alcohol.
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