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Organic Chemistry

Summary of Reactions

Organic ChemistrySummary of Reactions

26 • Summary of Reactions

26 • Summary of Reactions

  1. Amino acid synthesis (Section 26.3)
    1. From α-bromo acids
      A carboxylic acid reacts with bromine, phosphorus tribromide, and water to form a bromo-substituted acid that reacts with ammonia to form an amino acid.
    2. Diethyl acetamidomalonate synthesis
      Three-step reaction to form an R-substituted alpha amino acid via diethylacetamidomalonate reaction with sodium ethoxide, an alkyl halide (R X), and hydronium ion decarboxylation.
    3. Reductive amination of an α-keto acid
      An alpha-keto acid undergoes reductive amination in the presence of ammonia and sodium borohydride to form an alpha-amino acid.
    4. Enantioselective synthesis
      A (Z) enamido acid reacts with hydrogen, rhodium catalyst and boron tetrafluoride ion, sodium hydroxide, and water to form an (S)-amino acid.
  2. Peptide sequencing by Edman degradation (Section 26.6)
    An illustration shows a reaction wherein two reactants form two products. The first reactant shows a phenyl group bonded to nitrogen double bonded to carbon at the top which is double bonded to a green sulfur at the top. The second reactant shows a carbon bonded to another carbon at the top; the carbon at bottom is bonded to a blue amino group on the left wedge bonded to a hydrogen and dash bonded to R at the bottom right. The top carbon is double bonded to pink oxygen and single bonded to blue nitrogen monohydride bonded to an encircled peptide. The first product shows a cyclopentane with a nitrogen and blue nitrogen monohydride; the ring is double bonded to a pink oxygen and green sulfur; the nitrogen is bonded to a phenyl group; the bottom right position is wedge bonded to hydrogen and dash bonded to R. The second product shows a blue amino group bonded to an encircled peptide.
  3. Peptide synthesis (Section 26.7)
    1. Amine protection
      A zwitterionic amino acid reacts with di-tert-butyl pyrocarbonate in the presence of triethylamine to form a B o c-protected amino acid anion.
    2. Carboxyl protection
      An amino acid reacts with methanol and hydrochloric acid to form a methyl ester. The same reactant reacts with benzyl alcoholand hydrochloric acid to form a benzyl ester.
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