Learning Objective
- Identify the typical reaction that amides undergo.
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:
Note
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.
Example 17
Write the equation for the hydrolysis of each compound.
- butyramide
- benzamide
Solution
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The hydrolysis of a simple amide produces an organic acid and ammonia. Butyramide thus yields butyric acid and ammonia.
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The hydrolysis of an amide produces an organic acid and ammonia. Benzamide thus yields benzoic acid and ammonia.
Skill-Building Exercise
Write the equation for the hydrolysis of each compound.
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propionamide (propanamide)
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hexanamide
Concept Review Exercises
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What are the products of the hydrolysis of an amide?
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When the amide CH3CH2CH2CH2CONH2 is hydrolyzed in an NaOH solution, the products are CH3CH2CH2CH2COO−Na+ and NH3. What products are obtained when CH3CH2CH2CH2CONH2 is hydrolyzed in an hydrochloric acid solution?
Key Takeaway
- The hydrolysis of an amide produces a carboxylic acid and ammonia or an amine.
Exercises
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Complete each equation.
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Complete each equation.