{"id":1719,"date":"2018-03-21T15:43:22","date_gmt":"2018-03-21T15:43:22","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/chapter\/chemical-properties-of-amides-hydrolysis\/"},"modified":"2018-11-09T15:48:23","modified_gmt":"2018-11-09T15:48:23","slug":"chemical-properties-of-amides-hydrolysis","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-monroecc-orgbiochemistry\/chapter\/chemical-properties-of-amides-hydrolysis\/","title":{"raw":"15.17 Chemical Properties of Amides: Hydrolysis","rendered":"15.17 Chemical Properties of Amides: Hydrolysis"},"content":{"raw":"
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Learning Objective<\/h3>\r\n
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  1. Identify the typical reaction that amides undergo.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n

    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:<\/p>\r\n\r\n

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    Note<\/h3>\r\n

    Hydrolysis of an amide in acid solution actually gives a carboxylic acid and the salt<\/em> 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.<\/p>\r\n\r\n<\/div>\r\n<\/div>\r\n

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    Example 17<\/h3>\r\n

    Write the equation for the hydrolysis of each compound.<\/p>\r\n\r\n

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    1. butyramide<\/li>\r\n \t
    2. benzamide<\/li>\r\n<\/ol>\r\n

      Solution<\/p>\r\n\r\n

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        The hydrolysis of a simple amide produces an organic acid and ammonia. Butyramide thus yields butyric acid and ammonia.<\/p>\r\n\r\n

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        The hydrolysis of an amide produces an organic acid and ammonia. Benzamide thus yields benzoic acid and ammonia.<\/p>\r\n\r\n

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        Skill-Building Exercise<\/h3>\r\n

        Write the equation for the hydrolysis of each compound.<\/p>\r\n\r\n

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        1. \r\n
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          propionamide (propanamide)<\/p>\r\n\r\n<\/div><\/li>\r\n \t

        2. \r\n
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          hexanamide<\/p>\r\n\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n

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          Concept Review Exercises<\/h3>\r\n<\/div>\r\n
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          1. \r\n
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            What are the products of the hydrolysis of an amide?<\/p>\r\n\r\n<\/div><\/li>\r\n \t

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            When the amide CH3<\/sub>CH2<\/sub>CH2<\/sub>CH2<\/sub>CONH2<\/sub> is hydrolyzed in an NaOH solution, the products are CH3<\/sub>CH2<\/sub>CH2<\/sub>CH2<\/sub>COO\u2212<\/sup>Na+<\/sup> and NH3<\/sub>. What products are obtained when CH3<\/sub>CH2<\/sub>CH2<\/sub>CH2<\/sub>CONH2<\/sub> is hydrolyzed in an hydrochloric acid solution?<\/p>\r\n\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n

            \r\n\r\n[reveal-answer q=\"815818\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"815818\"]\r\n\r\n1. a carboxylic acid and ammonia or an amine\r\n\r\n2.CH3<\/sub>CH2<\/sub>CH2<\/sub>CH2<\/sub>COOH and NH4<\/sub>Cl[\/hidden-answer]\r\n
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            Key Takeaway<\/h3>\r\n