Reactions of Amides and Preparation of Nitriles

Vocabulary review of the reactions of primary amides (hydrolysis and hydride reduction) and the preparation methods of nitriles.

Acidic Hydrolysis of Amides

The reaction in which a primary amide ($R\text{CONH}_2$) is heated with aqueous acid ($H_3O^+$) to yield a carboxylic acid ($R\text{COOH}$).

Basic Hydrolysis of Amides

A two-step transformation in which a primary amide ($R\text{CONH}_2$) is treated with 1) $\text{NaOH}$, heat, followed by 2) $H_3O^+$ to yield a carboxylic acid ($R\text{COOH}$).

Reduction of Amides

The reaction converting a primary amide ($R\text{CONH}_2$) into a primary amine ($R\text{CH}_2\text{NH}_2$) using 1) excess $\text{LiAlH}_4$ and 2) $H_2O$.

Preparation of Nitriles from Alkyl Halides

The reaction of an alkyl bromide ($R-\text{Br}$) with sodium cyanide ($\text{NaCN}$) to produce a nitrile ($R-\text{C}\equiv\text{N}$).

Preparation of Nitriles from Amides (Dehydration)

The reaction of a primary amide ($R\text{CONH}_2$) with thionyl chloride ($\text{SOCl}_2$) to form a nitrile ($R-\text{C}\equiv\text{N}$).