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22.11: Summary of Reactions

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    1. Aldehyde/ketone halogenation (Section 22.3)
      A carbonyl group reacts with a haolgen in acetic acid to form an alpha halo carbonyl compound and H X as a byproduct.
    • Hell–Volhard–Zelinskii bromination of acids (Section 22.4)
      A carboxylic acid reacts with bromine and phosphorus bromide in one step and with water in a second step to form an alpha brominated carboxylic acid as the product.
    • Dehydrobromination of α-bromo ketones (Section 22.3)
      On heating, an alpha brominated ketone reacts with pyridine to form an alpha beta unsaturated ketone as the product.
    • Haloform reaction (Section 22.6)
      A methyl ketone reacts with a halogen and base to form a trihalomethane and a carboxylate ion.
    • Alkylation of enolate ions (Section 22.7)
      1. Malonic ester synthesis
        Diethyl malonate reacts with sodium ethoxide in ethanol and R X, followed by treatment with acid and heat gives a carboxylic acid product bearing an R group on the alpha carbon.
      2. Acetoacetic ester synthesis
        A ketone reacts with sodium ethoxide in ethanol and R X, followed by treatment with acid and heat gives an alpha alkylated ketone product.
      3. Direct alkylation of ketones
        An alkyl ester reacts with L D A in T H F in the first step and alkyl halide in the second step to yield an alpha alkylated ketone.
      4. Direct alkylation of esters
        An ester reacts with L D A in T H F in the first step and alkyl halide in the second step to yield an alpha alkylated ester.
      5. Direct alkylation of nitriles
        A nitrile reacts with L D A in T H F in the first step and alkyl halide in the second step to yield an alpha alkylated nitrile.

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