12.16: Chemical Properties of Amides- Hydrolysis
- Page ID
- 490468
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Generally, amides resist hydrolysis in plain water, even after prolonged heating. In the presence of added acid or base, however, hydrolysis proceeds at a moderate rate. In living cells, amide hydrolysis is catalyzed by enzymes. Amide hydrolysis is illustrated in the following example:
Hydrolysis of an amide in acid solution actually gives a carboxylic acid and the salt of ammonia or an amine (the ammonia or amine initially formed is neutralized by the acid). Basic hydrolysis gives a salt of the carboxylic acid and ammonia or an amine.
Write the equation for the hydrolysis of each compound.
- butyramide
- benzamide
Solution
- The hydrolysis of a simple amide produces an organic acid and ammonia. Butyramide thus yields butyric acid and ammonia.
- The hydrolysis of an amide produces an organic acid and ammonia. Benzamide thus yields benzoic acid and ammonia.
Write the equation for the hydrolysis of each compound.
- propionamide (propanamide)
- hexanamide
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Key Takeaway
- The hydrolysis of an amide produces a carboxylic acid and ammonia or an amine.