1. Knowledge and understanding: at the end of the course the student must have acquired the basic knowledge on the structure and reactivity of complex organic molecules and polyfunctional systems and must have understood at the fundamental level the structural and mechanistic principles underlying their biological role. He will also need to have knowledge of the basic laboratory techniques for the preparation and characterization of chiral molecules.
2. Applying knowledge and understanding: at the end of the course the student must have acquired the ability to predict the reactivity of complex organic molecules and the ability to propose a synthetic approach to their preparation. In addition, he must have acquired the knowledge necessary for the identification of simple organic molecules using NMR and MS techniques and must have acquired the knowledge and skills necessary for the execution of complex organic reactions also through the use of enzymes.
3. Making judgments: at the end of the course the student must be able to work independently in describing and predicting the reactivity of complex molecules, in designing synthesis and in making even complex chemical transformations in the laboratory.
4. Communication skills: at the end of the course the student must be able to clearly explain the concepts acquired in point 1 using a formally correct language.
5. Learning skills: at the end of the course the student must be able to independently deepen the topics covered in the course, including through the consultation of specialized texts, specific bibliography and chemical databases.

Organic Chemistry I and Organic Chemistry II with laboratory

Monocyclic and bicyclic pentatomic aromatic heterocyclic compounds: structure, preparation and reactivity.
Monocyclic and bicyclic hexatomic aromatic heterocyclic compounds: structure, preparation and reactivity.
Carbohydrates: structure and reactivity of monosaccharides; use of monosaccharides in organic synthesis; structure and properties of disaccharides, oligosaccharides and polysaccharides.
Lipids: fats, oils and glycerolphosphatides; structure and properties of terpenes and terpenoids, biosynthesis of terpenes; steroids.
Amino acids, peptides and proteins: structure, properties and synthesis of proteinogenic alpha-amino acids; properties of peptides; peptide synthesis in liquid in solid phase; structures and properties of polypeptides and proteins.
Nucleosides, nucleotides and polynucleotides: structure, properties and synthesis of oligonucleidites.
Nuclear magnetic resonance of carbon (13C-NMR).
Mass spectrometry (MS).
Experiences in laboratory:
1) synthesis of a homoallylic alcohol via Grignard's reaction;
2) Spectrophotometric identification of an unknown compound;
3) synthesis of Ala-Leu-OMe dipeptide.

For the general part the books suggested for the Organic Chemistry I and II courses.
For the chemistry of heterocyclic compounds: D. Sica; F. Zollo, Chimica dei Composti Eterociclici, Ed. EdiSES, Napoli, 2001; G. A. Pagani; A. Abbotto, Chimica Eterociclica, Ed. Piccin, Padova, 1995; J. A. Joule; G. F. Smith, Heterocyclic Chemistry, II Ed. Chapman-Hall Ed. 1992.
For the spectroscopic techniques:
“Identificazione spettrometrica di composti organici” seconda edizione, R.M. Silverstein, F.X. Webster, D. J. Kiemle, Casa editrice Ambrosiana

Heterocyclic compounds. Aromatic mono- and bicyclic pentaatomic heterocycles: pyrrole, furan, thiophene, indole and isoindole. Examples of synthesis and reactivity. Six member ring aromatic heterocycles. Pyridine and derivatives. Examples of synthesis and reactivity. Chinoline and isochinoline. Diazine.
Carbohydrates: Monosaccharide. Stereochemistry of aldose and chetose. Linear and cyclic forms of monosaccharide. The mutarotation. The anomeric effect. Examples of reactivity of monosaccharides. Structure and reactivity of disaccharides. Polysaccharides: starch, glycogen, cellulose, hyaluronic acid.
Lipids: Fats, Oils, Waxes. Phospholipids. Terpenes. Steroid. Biosynthesis of terpenes and cholesterol.
Amino acids, peptides and proteins. Structure and reactivity of alpha-amino acids. Synthesis and enantioselective synthesis of alpha-amino acids. Structure and properties of peptides. Determination of the N- and C-terminal amino acid. Peptide synthesis in solution and in solid phase. Proteins. Primary, secondary, tertiary and quaternary structure.
Nucleosides, nucleotides, and nucleic acids. Natural nucleosides and nucleotides. The protecting groups. Examples of synthesis of nucleosides and nucleotides. Synthesis of polynucleotides.
Nuclear magnetic resonance of carbon (13C-NMR): chemical shift, principal functional groups, coupling 1H-13-C, 1H decoupled spectra, DEPT, analysis of 13C-NMR spectra of organic compounds.
Mass spectrometry (MS): ionization techniques, detectors, nitrogen rule, isotopic peaks, simple fragmentations.
Experiences in laboratory:
1) synthesis of a homoallylic alcohol via Grignard's reaction;
2) Spectrophotometric identification of an unknown compound;
3) synthesis of Ala-Leu-OMe dipeptide.

Classroom lectures with exercises and powerpoints. Exercises in the chemical laboratory. In parallel to the laboratory lessons, the student will have to perform multiple choice tests and upload the reports using the Moodle platform.

On the MOODLE platform are available the powerpoints used in class and materials for the lab.

The final exam consists of an oral test that focuses on the topics covered in class and the discussion of reports on the experiences carried out in the laboratory. The oral exam consists of 3/4 questions aimed at ascertaining an adequate knowledge of the topics covered in the course. In the oral examination the student must demonstrate that he has acquired a technically correct language and that he is able to correctly describe the structure, the chemical / physical and stereochemical properties and the reactivity of the molecules, the reaction mechanisms and the theoretical concepts acquired in the course. In the discussion of laboratory reports the student must have completed the tests on Moodle, and will have to demonstrate that he understands the methodologies and techniques used and will have to critically discuss the results obtained.

This course explores topics closely related to one or more goals of the United Nations 2030 Agenda for Sustainable Development (SDGs) as Organic Chemistry is the basis of the processes of discovery of new drugs and also of processes for the development of sustainable chemistry.