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Organic Chemistry

Summary of Reactions

Organic ChemistrySummary of Reactions

22 • Summary of Reactions

22 • Summary of Reactions

  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.
  2. 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.
  3. 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.
  4. Haloform reaction (Section 22.6)
    A methyl ketone reacts with a halogen and base to form a trihalomethane and a carboxylate ion.
  5. 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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