Organic Chemistry Ii

Goals
The course is a continuation of Organic Chemistry I and aims at providing an introduction to the chemistry of aromatic compounds. Additional topics include the chemistry of biologically relevant organic molecules.

Acquired skills
Knowledge of structure, nomenclature, properties, synthesis and reactivity of aromatic compounds (both carbocyclic and heterocyclic) as well as of some biomolecules such as carbohydrates, aminoacids, peptides.

Course content
Monocyclic aromatic compounds.
Benzene: principles of aromaticity, resonance, the Hückel rule. Nomenclature. Electrophilic aromatic substitution: mechanism and orientation. Halogenation, alkylation, acylation, nitration, sulfonation. Nitro compounds. Aromatic amines: synthesis and reactivity. Diazonium salts and their industrial importance. Aryl sulfonic acids. Sulfonamides. Aromatic halogen compounds: synthesis and reactivity. Nucleophilic aromatic substitution. Phenols and phenyl ethers. Fries and Claisen rearangements. Kolbe synthesis. Reaction with formaldehyde, Reimer-Tiemann and copulation reactions. Quinones. preparation and reactivity. Oxidation and reduction of aromatic compounds. Side-chain reaction: benzyl radical and carbocation.
Polycyclic aromatic compounds.
Biphenyls and atropisomerism. Fluorene and analogs. Naphthalene: synthesis, halogenations, sulfonation, nitration and Friedel-Crafts reactions. Anthracene and phenanthrene.
Heterocyclic compounds.
Classification and nomenclature. Heteroaromaticity. Synthesis and reactivity of five-membered heterocycles: pyrrole, furan and thiophene. Indole. Pyridine: structure, synthesis and properties. Pyridine N-oxide. Nucleophilic substitution. Quinoline and isoquinoline. Examples of biologically active heterocyclic compounds: pyrimidine and purine bases, nucleotides.
Amino acids and peptides.
Alpha-amino acids: structure, nomenclature, acid-base properties, isoelectric point, titration curves, stereochemistry, separation. Synthesis and resolution of amino acids. Protecting groups. Synthesis of peptides. Solid-phase synthesis.
Carbohydrates.
Classification and nomenclature. Monosaccharides: structure, stereochemistry, Fischer projections and reactivity. Cyclic hemiacetals. Mutarotation. Formation of glycosides. Reducing sugars. Oxidation and reduction. Chain lengthening and shortening. Disaccharides: sucrose, maltose, lactose. Polysaccharides.

Suggested prerequisites
Organic Chemistry I course

Reference material
- Any comprehensive textbook of Basic Organic Chemistry
- John D. Hepworth, David R. Waring and Michael J. Waring, Aromatic Chemistry, Royal Society of Chemistry, Cambridge, 2002

Assessment method
Written and oral examination.
The exam consists of two compulsory parts: a written test and an oral test. The written test will include problems related to all the topics discussed in the course. In the oral exam the conceptual as well as theoretical aspects of the subject will be assessed.

Language of instruction
Italian

Attendance Policy:
Attendance is highly recommended

Mode of teaching:
Traditional

Website:
https://gsperanzaco2.ariel.ctu.unimi.it/v5/home/Default.aspx