Basic knowledge of general chemistry, physics and mathematics
To provide basic knowledge to understand the scientific methodology in organic chemistry.
Knowledge and understanding. The student will have to know the fundamental principles of organic chemistry so that, starting from the study of functional groups in simple molecules, he will be able to understand the reactions that take place in biological systems and in food.
Ability to apply knowledge and understanding. The student should be able to assign the IUPAC name to organic molecules, recognize the various types of chemical reactions and complete reaction schemes.
Judgment autonomy. The student should be able to understand and critically discuss the mechanism of organic chemistry reactions.
Communication skills. The student must demonstrate that he can communicate effectively and with the correct terminology.
Learning ability. The student must be able to read, understand and comment on a scientific text of organic chemistry.
One of the following: McMurry, J. “Fondamenti di chimica organica”, Zanichelli, ISBN 9788808061317; McMurry, J. “Chimica organica. Un approccio biologico”, Zanichelli, ISBN 8808066932; Botta, B. “Chim-
ica organica essenziale”, Edi-ermes, ISBN 9788870513547. The texts must be supplemented by lecture notes.
Verification of learning consists of a written test and an oral test. The written test lasts 2 hours. The purpose of the test is to ascertain the level of specific knowledge reached by the student in organic chemistry. The exam consists of 10 questions.
The oral test lasting about 20 minutes, during which questions (on average 3) are asked on topics from the teaching program.
For the oral exam, the level of achievement of the learning outcomes expected from the teaching will be ascertained, as well as the clarity of presentation and language properties.
In case of failure to achieve a sufficient level of learning, the student will be invited to deepen the specific topics in which it is lacking, also making use of further explanations by the teacher.
1. Introduction (0.5 CFU). Carbon atom, sp3, sp2, sp hybridization. Intermolecular bonds: dipole-dipole, hydrogen, van der Waals bond. Elements of thermodynamics: enthalpy, entropy, free energy. Chemical kinetic: kinetic equation, activation energy, catalysis. Acidity, Brønsted and Lewis acid.
2. Alkanes (0.75 CFU). Nomenclature and physical properties. Cycloalkanes. Radical halogenation. Conformational analysis. Newman and Fischer formulas. Energy diagrams. Conformational analysis in linear and cyclic molecules.
Stereochemistry. Optical activity, chirality. Enantiomers, diastereomers, meso structures. Configuration R,S and D,L. Resolution racemic mixtures.
3. Alkenes, alkynes and aromatic compounds (1 CFU). Nomenclature and physical properties. Carbocations: structure and reactivity. Reactivity with: H2, HX (X = Br, Cl), H2O/H2SO4, X2 (X = Br, Cl), KMnO4, OsO4, peroxyacids. Allylic halogenations. Conjugated dienes: 1,2- and 1,4-addition. Alkynes. Nomenclature, reaction with H2.
Aromatic compounds. Benzene. Aromaticity, Hückel rule. Resonance. Electrophilic aromatic substitution: nitration, sulfonation, halogenation, Friedel-Crafts acylation and alkylation. Benzene derivatives: structure and reactivity. Rate and regioselectivity. Inductive and conjugative effect. Oxidation of alkylbenzenes with KMnO4. Reduction of nitrobenzene with Fe/HCl.
Alkyl halides. Reactions: SN1, SN2, E1, E2. Nucleophilicity, basicity. Grignard reagents.
4. Alcohols and phenols (0.5 CFU). Nomenclature and physical properties. Acid-base reactions, oxidation, dehydration, chlorination and esterification reactions. Thiols.
Ethers. Nomenclature and physical properties. Epoxides: ring-opening reactions.
5. Aldehydes, ketones and amines (0.5 CFU). Nomenclature and physical properties. Reactivity with: H2, hydrides, Grignard reagents, HCN, H2O, ROH, NH2R. Aldehydes: oxidation.
Amines. Nomenclature and physical properties. Basicity. Quaternary ammonium salts. Reaction of primary amines with HNO2. Diazonium salts.
6. Carboxylic acids and derivatives (0.75 CFU). Nomenclature and physical properties. Acidity of carboxylic acids. Synthesis and reactions of acid chlorides, anhydrides, esters, amides. Saponification of esters. Reduction with LiAlH4. Amides, physical properties. Nitriles, acid and basic hydrolysis.
Enols. Acidity of carbonyl compounds. Keto-enol tautomerism. Aldol and Claisen condensation.
7. Bifunctional compounds (0.5 CFU). Amino acids, hydroxy acids, keto acids and dicarboxylic acids. Carbonyl compounds, decarboxylation. Acetoacetic and malonic ester synthesis.
Heterocyclic compounds. Pyrrole: aromaticity, acidity and basicity, electrophilic aromatic substitution. Pyridine: basicity, nucleophilic and electrophilic aromatic substitution. Imidazole: acidity and basicity. Purine and pyrimidine.
8. Carbohydrates and lipids (0.5 CFU). Classification. Monosaccharides. Reaction of monosaccharides with: NH2NHPh, Br2, HNO3, NaBH4, ROH. Reducing sugars. Hemiacetals and acetals, alpha and beta anomers, mutarotation. Haworth and conformational formulas, furanose and pyranose forms. Polysaccharides: starch and cellulose.
Lipids. Fatty acids, autooxidation. Triglycerides, hydrolysis and hydrogenation. Natural and synthetic detergents, micelle formation. Phospholipids, formation of bilayers.
9. Classroom exercises (1 CFU). The exercises consist in the explanation and comment of exercises in the reference books and in the written tests of the previous academic years. The exercises cover all treated topics.