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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
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    Key Takeaway

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

    This page titled 15.16: Chemical Properties of Amides- Hydrolysis is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by Anonymous via source content that was edited to the style and standards of the LibreTexts platform.