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21.14: Summary of Reactions

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    1. Reactions of carboxylic acids (Section 21.3)
      1. Conversion into acid chlorides
        Conversion of a carboxylic acid to an acid chloride, by reaction with thionyl chloride in trichloromethane (chloroform). The hydroxyl group is replaced by a chlorine atom.
    • Conversion into esters
      At the top, reaction of a carboxylate ion with an alkyl halide to give an ester through an S N 2 mechanism. At the bottom, reaction of a carboxylic acid with an alcohol to yield an ester.
    • Conversion into amides
      Conversion of a carboxylic acid to an N-substituted amide by reaction with a monosubstituted amine and D C C.
    • Reduction to yield primary alcohols
      Conversion of a carboxylic acid to a primary alcohol using lithium aluminum hydride.
    • Reactions of acid chlorides (Section 21.4)
      1. Hydrolysis to yield acids
        Hydrolysis of an acid chloride using water to give a carboxylic acid and hydrochloric acid.
      2. Reaction with carboxylates to yield anhydrides
        Reaction of an acid chloride with a carboxylate in to form an acid anhydride.
      3. Alcoholysis to yield esters
        The reaction of an acid chloride with an alcohol in the presence of pyridine to form an ester.
      4. Aminolysis to yield amides
        Two molecules of ammonia react with an acid chloride to form an amide and ammonium chloride.
      5. Reduction to yield primary alcohols
        Reaction of an acid chloride with lithium aluminum hydride in ether followed by treatment with acid to generate an alcohol.
      6. Grignard reaction to yield tertiary alcohols
        Reaction of an acid chloride with two moles of Grignard reagent in ether followed by treatment with acid to give a tertiary alcohol.
      7. Diorganocopper reaction to yield ketones
        An acid chloride reacts with diorganocopper-lithium (Gilman reagent) in ether to form an ester.
    • Reactions of acid anhydrides (Section 21.5)
      1. Hydrolysis to yield acids
        Reaction of an acid anhydride with water gives two equivalents of carboxylic acid.
      2. Alcoholysis to yield esters
        The reaction of an acid anhydride with an alcohol forms an ester and a carboxylic acid.
      3. Aminolysis to yield amides
        The reaction of an acid anhydride with two equivalents of ammonia gives an amide and an ammonium carboxylate salt.
    • Reactions of esters (Section 21.6)
      1. Hydrolysis to yield acids
        An ester is hydrolyzed to a carboxylic acid and alcohol using either acid or base.
      2. Reduction to yield primary alcohols
        An ester is reduced to an alcohol using lithium aluminum hydride in ether followed by treatment with acid.
      3. Partial reduction to yield aldehydes
        An ester is partially reduced to an aldehyde using D I B A H in toluene followed by treatment with acid.
      4. Grignard reaction to yield tertiary alcohols
        The reaction of an ester with a Grignard reagent in ether followed by treatment with acid produces an alcohol
    • Reactions of amides (Section 21.7)
      1. Hydrolysis to yield acids
        Hydrolysis of an amide to a carboxylic acid using acid or base.
      2. Reduction to yield amines
        Reduction of amides to amines using lithium aluminum hydride in ether followed by treatment with acid.

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