On the basis of the general mechanism for basic hydrolysis shown in Mechanism 20.5, write...

On the basis of the general mechanism for basic hydrolysis shown in Mechanism 20.5, write an analogous sequence for the hydrolysis of N,N-dimethylformamide,

Mechanism 20.5

Amide Hydrolysis in Basic Solution

THE OVERALL REACTION:

THE MECHANISM:

Step 1: Nucleophilic addition of hydroxide ion to the carbonyl group

Step 2: Proton transfer to the anionic form of the tetrahedral intermediate

Step 3: Protonation of the amino nitrogen

Step 4: Dissociation of the N-protonated form of the tetrahedral intermediate

Step 5: Irreversible formation of the carboxylate anion