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Esame organica 2
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- Carbohydrate Structure Elucidation (Problem 1):
- Analysis of disaccharide G (C11H20O10), yielding D-glucose and a D-pentose via α-glucosidase.
- G is non-reducing (Fehling's test).
- Methylation of G yields heptamethyl ether K.
- Hydrolysis of K produces 2,3,4,6-tetra-O-methyl-D-glucose and tri-O-methyl pentose W, indicating linkage positions.
- W's reduction with NaBH4 gives an optically inactive product; Br2 oxidation yields D-ribonic acid, identifying W as D-ribose.
- Deduce full structures of G, K, and W based on these data.
- Organic Synthesis (Problem 2):
- Propose synthesis for 3-ethoxy-2,4-dimethylpentane.
- Starting materials limited to a maximum of 3 carbon atoms.
- This involves carbon-carbon bond formation and ether synthesis (e.g., Grignard reactions, Williamson ether synthesis).
- Chemical Transformations (Problem 3):
- Transformation 3.1: Convert N-phenyl-N'-(2-aminophenyl)oxamide to 2-((imino)benzo[d][1,3]oxazol-3-yl)-N-phenylacetamide, requiring complex intramolecular cyclization to form a heterocyclic system.
- Transformation 3.2 (Peptide Synthesis): Form N-phenylglycylglycine from N-phenylglycine. This involves standard peptide coupling techniques, likely utilizing activation of the carboxylic acid and appropriate amine protection.
- Transformation 3.3 (Aromatic Amination): Introduce an amino group onto a naphthalene derivative, specifically transforming Naphthalene-1-ol-4-sulfonic acid into an aminated product. This could involve electrophilic aromatic substitution (nitration/reduction) or specific amination reactions for aromatic systems.
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