Which of the following species does not represent an intermediate in the acid-catalyzed hydrolysis of propionamide to propanoic acid?

Step-by-step solution

The acid-catalyzed hydrolysis of propionamide to propanoic acid proceeds via the following steps: 1. Protonation of the carbonyl oxygen of propionamide forms a resonance-stabilized cation: CH₃CH₂CONH₂ + H^+ CH₃CH₂C(=O^+H)NH₂ CH₃CH₂C(OH)=N^+H₂ This matches the species in Option (A). 2. Nucleophilic attack by water on the electrophilic carbon, followed by proton transfer, yields a tetrahedral intermediate where the nitrogen is protonated to make it a good leaving group: CH₃CH₂C(OH)(OH₂^+)NH₂ CH₃CH₂C(OH)₂N^+H₃ This ma