When these two amides undergo hydrolysis under identical reaction conditions, it is found that amide A reacts significantly faster (1000 times) than does amide B.
a. Draw the structure of each hydrolysis product in the appropriate box.
b. Using concepts developed in this course, and using structures and reaction coordinate diagrams, explain the above indicated difference in the hydrolysis rates. (Assume the ring strains in amides A and B are essentially equal, and the tetrahedral intermediates (TIs) for both reactions are of about equal energy.)

Question

When these two amides undergo hydrolysis under identical reaction conditions, it is found that amide A reacts significantly faster (>1000 times) than does amide B.
a. Draw the structure of each hydrolysis product in the appropriate box.
  b. Using concepts developed in this course, and using structures and reaction coordinate diagrams, explain the above indicated difference in the hydrolysis rates. (Assume the ring strains in amides A and B are essentially equal, and the tetrahedral intermediates (TIs) for both reactions are of about equal energy.)

Quizplus · Accepted Answer

The Answer of When these two amides undergo hydrolysis under identical reaction conditions, it is found that amide A reacts significantly faster (>1000 times) than does amide B.
a. Draw the structure of each hydrolysis product in the appropriate box.
  b. Using concepts developed in this course, and using structures and reaction coordinate diagrams, explain the above indicated difference in the hydrolysis rates. (Assume the ring strains in amides A and B are essentially equal, and the tetrahedral intermediates (TIs) for both reactions are of about equal energy.)

When These Two Amides Undergo Hydrolysis Under Identical Reaction Conditions