A-level Chemistry/OCR (Salters)/Nitrile hydrolysis

Nitrile hydrolysis proceeds by the mechanism outlined below. It begins with protonation of the nitrile nitrogen, which increases the partial positive charge on carbon and therefore renders carbon more susceptible to nucleophilic attack by a water molecule. Addition of water to the nitrile is the key step in nitrile hydrolysis − the next few steps are simple proton transfers, until an amide is formed. The amide then typically undegoes further hydrolysis to a carboxylic acid. Summary 400px Step 1: Protonation 200px Step 2: Nucleophilic attack of water at carbon 200px Step 3: Intramolecular proton transfer 150px Step 4: Deprotonation 160px Step 5: Amide formed 150px