The target of the course is to give a more inside knowledge of the Organic Chemistry respect to the first course, in particular relating to the chemical properties and reactivity. The main topics of the course will be carbohydrates, aminoacids and peptides, lipids, heterocycles. The course includes also 2 CFU of laboratory. During this activity, the target of the course will be the knowledge of the laboratory glass, and the ability to start a chemical reaction. Furthermore, the final target will be the use of some spectroscopic techniques, such as NMR, UV and IR, to establish the chemical structure of a unknown compound.
The course is divided into two parts: frontal lessons (in classroom) and laboratory activity. The frequency is mandatory.
Carbohydrates: Classification of carbohydrates - The D and L notation - Configuration of aldoses - Configuration of ketoses - Reactions of monosaccharides in basic solution - Reduction reactions of monosaccharides - Lengthening of the chain: the Kiliani-Fischer synthesis - Shortening of the chain: degradation of Wohl - Monosaccharides form cyclic hemiacetals - Formation of glycosides - The anomeric effect - Reducing and non-reducing sugars - Mutarotation - Disaccharides - Polysaccharides.
Amino acids, peptides and proteins: Nomenclature of amino acids - Configuration of amino acids - Acid-base properties of amino acids - The isoelectric point - Separation of amino acids - Methods of synthesis of amino acids - Resolution of a racemic mixture of amino acids - Peptide bonds and disulfide bonds - Peptide synthesis strategies - Peptide synthesis automated - Introduction to the structure of proteins - How to determine the primary structure of a polypeptide or a protein - Secondary structure of proteins - Tertiary structure of proteins - Quaternary structure of proteins.
pericyclic reactions: Conjugated dienes, molecular orbitals and symmetry, electrocyclic reactions, cycloadditions, sigmatropic transpositions, electrophilic additions, Dies-Alder, pericyclic reactions
Organometallic compounds and formation of new C-C bonds: C-C coupling reactions: irreversible covalent synthetic methodologies. Formation of new C-C bonds. Suzuki, Stille, Heck, Sonogashira, Negishi. Formation of new C = C bonds: Metathesis; Click Chemistry
Retrosynthesis: Basic principles of disconnections, Disconnection methodologies: synthesis of aromatic compounds, order of events, CX disconnections, chemoselectivity, synthesis of amines, protecting groups, CC disconnections (alcohols, aldehydes and ketones, carbonyl compounds), regioselectivity in ketone alkylations, disconnection of alkenes (elimination from alcohols, Wittig synthesis of dienes), use of acetylene.
Nucleic acids: Nucleosides and nucleotides, Other important nucleotides, DNA structure, Ribonucleic acids and RNA transcription, Genetic code.
PHYSICAL METHODS IN ORGANIC CHEMISTRY
General principles of absorption spectroscopy. UV-VIS and IR spectroscopy. General principles and examples of applications to organic molecules.
Gas chromatography. Essential factors inherent in the gas chromatographic technique. Chromatographic columns. High Pressure Liquid Chromatography (HPLC). General principles.
NMR spectroscopy, Fourier transform NMR, Screen effect, multiplicity of signals, chemical shift, diamagnetic anisotropy, integration of signals, coupling constants. 13C NMR spectroscopy, two-dimensional NMR spectroscopy.
LABORATORY EXERCISES
Use of TLC for the identification of different organic substances present in the mixture: how do you proceed to choose the most suitable eluent mixture?
Practical execution of reactions of:
Electrophilic aromatic substitution: p-nitroaniline synthesis (protective groups).
Multistep synthesis: preparation of a local anesthetic (benzocaine), nucleophilic acyl substitution.
Isolation, purification and characterization of the products obtained in the single experiments by means of: melting point, UV-Vis, IR, 1H- and 13C-NMR.