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20.12: Summary of Reactions

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    1. Preparation of carboxylic acids (Section 20.5)
      1. Carboxylation of Grignard reagents
        Organomagnesium halide reacts with carbon dioxide followed by acid hydrolysis to produce a carboxylic acid. Carbon dioxide's carbon becomes the carboxyl.
    • Hydrolysis of nitriles
      Nitrile reacts with hydronium or sodium hydroxide and water to produce carboxylic acid. Nitrile carbon becomes the carboxyl.
    • Preparation of nitriles (Section 20.7)
      1. SN2 reaction of alkyl halides
        Alkyl bromide reacts with sodium cyanide to produce a nitrile. Cyanide carbon becomes nitrile carbon.
    • Dehydration of amides
      An amide reacts with thionyl chloride to form nitrile, sulfur dioxide, and two equivalents of hydrogen chloride. Carbonyl carbon becomes nitrile carbon.
    • Reactions of nitriles (Section 20.7)
      1. Hydrolysis to yield carboxylic acids
        Nitrile reacts first with sodium hydroxide and water, then with hydronium to produce carboxylic acid and ammonia. Nitrile nitrogen becomes ammonia nitrogen.
      2. Reduction to yield primary amines
        Nitrile reacts first with lithium aluminum hydride, then with water to produce a primary amine. Nitrile nitrogen becomes amine nitrogen.
      3. Reaction with Grignard reagents to yield ketones
        Nitrile reacts first with organomagnesium bromide in ether, then with hydronium to produce a ketone and ammonia.

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