MolSynapsequestion bank
MolSynapse / Question bank / Aldehydes, Ketones and Carboxylic Acids / Acidity order and derivative reactivity among drawn carboxylic acids
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3co272

The anhydride shown reacts with nucleophiles. Which statements are correct?

  1. AWith ethanol it gives an ester and a carboxylic acid
  2. BWith excess ammonia it gives an amide and an ammonium carboxylate
  3. CIt is more reactive than the corresponding ethyl ester because carboxylate is a better leaving group than alkoxide
  4. DIt is less reactive than the corresponding acid chloride but more reactive than a simple amide

Answer: A, B, C, D

The drawn compound is ethanoic anhydride. Nucleophilic acyl substitution releases carboxylate: with EtOH it gives ethyl ethanoate + ethanoic acid, with excess NH3 gives ethanamide + ammonium ethanoate. Carboxylate is a better leaving group than ethoxide, so the anhydride exceeds the ester in reactivity, and the order is RCOCl > anhydride > ester > amide. All four statements are correct.
Practice Aldehydes, Ketones and Carboxylic Acids More on Acidity order and derivative reactivity among drawn carboxylic acids

More questions on Acidity order and derivative reactivity among drawn carboxylic acids