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SolutionsCarboxylic Acid Derivatives

1. Identify the derivative

Which family does each compound belong to? a) CH3COOCH2CH3; b) CH3CONH2; c) CH3COCl; d) (CH3CO)2O; e) CH3CN.

  1. Ester (ethyl acetate).
  2. Amide (acetamide).
  3. Acyl halide (acetyl chloride).
  4. Anhydride (acetic anhydride).
  5. Nitrile (acetonitrile).

2. Order of reactivity

Arrange in order of decreasing reactivity towards a nucleophile: amide, acid chloride, ester and anhydride. What is the order based on?

Acid chloride > anhydride > ester > amide.

The more the L group donates electrons to the carbonyl (by resonance), the less electrophilic the carbon is and the poorer a leaving group L is. The amide nitrogen donates a lot; chlorine, hardly anything.

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