Provide an example of the nucleophilic substitution of different amides.

Nucleophilic substitution of amides can occur with different nucleophiles, such as hydroxide ions or amines.

Amides are compounds that contain a carbonyl group (C=O) and an amino group (NH2) attached to the same carbon atom. Nucleophilic substitution reactions involve the replacement of one nucleophile with another. In the case of amides, the carbonyl group is the electrophile (electron-deficient) site and can be attacked by a nucleophile, leading to the formation of a new compound.

One example of nucleophilic substitution of amides is the hydrolysis of amides with hydroxide ions. This reaction involves the attack of the hydroxide ion on the carbonyl carbon, leading to the formation of a tetrahedral intermediate. This intermediate then collapses, breaking the C-N bond and forming a carboxylate ion and an amine.

Another example is the reaction of amides with amines, which can lead to the formation of new amides. This reaction involves the attack of the amine on the carbonyl carbon, leading to the formation of a tetrahedral intermediate. The intermediate then collapses, breaking the C-N bond and forming a new amide.

Overall, nucleophilic substitution of amides can lead to the formation of a variety of compounds, including carboxylic acids, amine salts, and new amides. These reactions are important in the synthesis and breakdown of biological molecules, such as proteins and nucleic acids.