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15.16: Chemical Properties of Amides- Hydrolysis

  • Page ID
    16039
    • Anonymous
    • LibreTexts
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    Learning Objectives
    • To 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:

    clipboard_e69269df5e39caed767729fe18f975623.png

    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 \(\PageIndex{1}\)

    Write the equation for the hydrolysis of each compound.

    1. butyramide
    2. benzamide
    Solution
    1. The hydrolysis of a simple amide produces an organic acid and ammonia. Butyramide thus yields butyric acid and ammonia.

      clipboard_e6a555005fad0de25363fad726d6de540.png

    • The hydrolysis of an amide produces an organic acid and ammonia. Benzamide thus yields benzoic acid and ammonia.

      clipboard_e40233ea6fc0a21cf529059999426e7cc.png

    Exercise \(\PageIndex{1}\)

    Write the equation for the hydrolysis of each compound.

    1. propionamide (propanamide)
    2. hexanamide
    Career Focus: Athletic Trainer

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    Athletic trainers may have administrative duties, such as the responsibility for ordering supplies. They also need to be able to evaluate nutritional supplements because providing the wrong one can get an athlete banned from competition and may bring sanctions against a school. In short, the athletic trainer is responsible for the overall health and well-being of the athletes in his or her charge.

    Key Takeaway

    • The hydrolysis of an amide produces a carboxylic acid and ammonia or an amine.

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