LEARNING OUTCOMES

Acquire the fundamental concepts that allow to understand the structure and reactivity of the main classes of organic compounds, with particular emphasis on the biologically important reactions. Acquire a basic knowledge of the main primary metabolites. To be able to execute some of the typical practical procedures of an organic chemistry laboratory. To be able to work in group and to write a laboratory report.

AIMS AND LEARNING OUTCOMES

Knowledge and understanding

Provide the fundamental concepts that allow to understand the structure and reactivity of the main classes of organic compounds, with particular emphasis on the biologically important reactions.

Provide the instruments to acquire a basic knowledge of the main primary metabolites; to be able to execute some of the typical practical procedures of an organic chemistry laboratory; to be able to work in group; to write a laboratory report.

Skills and abilities

Students have to be able to: know and understand the structures of the main organic compounds; know how to write the structural formulas of organic substances correctly; recognize the molecular diversity based on the chemical structures (isomerism); know the main organic reactions; predict the products of a given reaction by evaluating the kinetic and thermodynamic aspects; know and understand the main primary metabolites (carbohydrates, proteins, lipids, nucleic acids); know how to perform the common purification techniques of organic compounds; carry out some reactions of basic organic chemistry; use some analytical tools for the characterization of organic compounds; write correctly a laboratory report; to work in team.

PREREQUISITES

The fundamental concepts of general chemistry acquired during the course of General Chemistry in the first semester

TEACHING METHODS

Traditional lessons in the classroom (52 hours). The solutions of problems will be treated in additional and optional tutoring hours (10). Laboratory sessions (7 sessions of 4 hours each).

The attendance is compulsory. Students must attend all laboratory sessions and 60% of the classroom lessons.

SYLLABUS/CONTENT

1. Introduction and unfunctionalised compounds (6 hours). 1.1 Introduction. 1.2 The chemical bond in organic compounds. 1.3 Alkanes
2. Survey of the main functional groups: physical and acid-base properties. Purification/separation techniques (8 hours). 2.1 Survey of the main functional groups and elements of nomenclature. 2.2 Non-bonding interactions and physical properties. 2.3 Acid-base properties of organic compounds. 2.4 Separation through extraction. 2.5 Crystallization. 2.6 Distillation. 2.7 Chromatography.
3. Stereochemistry (6 hours). 3.1 Conformations. 3.2 Types of stereoisomers, chirality, R/S notations. 3.3 Compounds with two stereogenic carbons. 3.4 Polarimetry. 3.5 Enantiomeric mixtures. 3.6 Equivalent stereogenic centres. 3.7 Chemical and biological properties of enantiomers. 3.8 Classical resolution through diastereomeric salts. 3.9 E/Z isomety in alkenes.
4. Reactions of C=C double bonds (5 hours). 4.1 Thermodynamic and kinetic aspects of reactions. 4.2 Alkene hydrogenation. 4.3 Electrophilic addition to C=C double bond, Markovnikov rule. 4.4 Benzene and aromaticity. 4.5 Heteroaromatic compounds and their basic properties. 4.6 Electrophilic substitution on benzene. 4.7 Keto-enol tautomerism in carbonyl compounds, phenols and heteroaromatic compounds.
5. Reactions of C=O double bonds (7 hours). 5.1 Nucleophilic additions to carbonyl compounds. 5.2 Acyl nucleophilic substitution. 5.3 Other carboxylic derivatives. 5.4 Acyl nucleophilic substitution in biology. 5.5 Reactions of carbon nucleophiles at the α positions of carbonyl.
6. Redox reactions of the main organic compounds (chemical and biological) (6 hours). 6.1 Determination of oxidation number. 6.2 Oxidation and reduction of oxygenated organic compounds. 6.3 Alkene oxidations. 6.4 Quinones. 6.5 Redox reaction at N or S.
7. Aminoacids and peptides (2 hours)
8. Carbohydrates (4 hours). 9.1 Structure and stereochemistry of main monosaccharides. 9.2 Mutarotation. 9.3 Glicosides. 9.4 Monosaccharide oxidations and reductions. 9.5 Polysaccharides.
9. Lipides (1 hours). 10.1 Triglycerides - soaps - waxes. 10.2 Phospholipides.
10. Nucleic acids (1 hours)
11. Radical reactions (2 hours)
12. Exercises (five 2 hour sessions)(optional; extra-CFU): exercises on programme subjects.
13. Laboratory: seven 4 hour sessions.

RECOMMENDED READING/BIBLIOGRAPHY

1. Slides of lessons (published on aula web)
2. Exercises and solutions (published on aula web)
3. W. H. Brown, "Introduzione alla Chimica Organica", EdiSES
4. J. McMurry "Fondamenti di Chimica Organica", Zanichelli
5. B. Botta "Chimica Organica Essenziale", EDI-Ermes.
6. J.G. Smith "Fondamenti di Chimica Organica", McGraw Hill
7. L.G. Wade "Fondamenti di Chimica Organica", Piccin
8. D. Klein, "Fondamenti di Chimica Organica", Pearson
9. P. Y. Bruice, «Elementi di Chimica Organica», EdiSES