Derivatives: esters, acid chlorides, amides, anhydrides
Carboxylic Acids and Derivatives · Chemistry
Study notes
Why is acetyl chloride fuming and reactive but acetamide stable? Step 1: Reactivity depends on the leaving group and carbonyl electrophilicity. Step 2: Cl⁻ is an excellent leaving group; –NH₂ is terrible (strong base). Step 3: N's lone pair donates into C=O (resonance) → less δ⁺ on carbon. Step 4: Order: RCOCl > (RCO)₂O > RCOOR' > RCONH₂. Leaving group + resonance decide!