_” MECHANISM FOR ACID-CATALYZED HYDROLYSIS OF AMIDE “_

Technically, the hydrolysis reaction with water. That's what happens when amidadihidrolisis (with a dilute acid such as dilute hydrochloric acid, this acid acts as a catalyst for the reaction between amide and water).

1.      Hydrolysis Amide in acidic conditions

When the amide is hydrolyzed in acidic conditions, acid proton of the carbonyl oxygen, increase the susceptibility of the carbonyl carbon to nucleophilic attack. Nucleophilic attack by water on the carbonyl carbon causes the tetrahedral intermediate compound I, which is in equilibrium with form rather than protons, tetrahedral intermediate II.

Reprotonasi can occur either at the tetrahedral intermediates of oxygen to reform the I or the nitrogen to form a tetrahedral intermediate III. Protonation at nitrogen is preferred because the NH₂ group is a stronger base than OH groups. Of the two possible groups to go on a tetrahedral intermediate III group (-OH and NH₃), NH₃ is a weak base, so it is released, forming carboxylic acids as end products. Because the reaction is carried out in acid solution, NH₃ be protonated after expelled from the tetrahedral intermediates. This prevents the reverse reaction.

WHY AMIDE CAN’T HYDROLYSED WITHOUT A CATALYST?

In the reaction without a catalyst, not the protonated amide. Therefore, the water, a very poor nucleophile, to attack neutral amides are much more susceptible to nucleophilic attack than the protonated amide. In addition, the group of the tetrahedral intermediate is not protonated in the reaction without a catalyst. By the because it,-OH is a group go from tetrahedral medium--because-OH is an basa who weak from the-NH2 amide such reforms. An amide to react with alcohols under acidic conditions for the same reason will react with water under acidic conditions.