ORGANIC CHEMISTRY

Basic knowledge of organic compounds, of their three-dimensional structure and of their reaction mechanisms.

In particular, the specific training objectives of this course are:

- Understanding the chemical bond in organic compounds;

- Understanding the three-dimensional structure (stereochemical) of organic compounds;

- Understanding the relationship between structure and chemical reactivity;

- Understanding the reaction mechanisms of organic compounds;

- Understanding the kinetic and thermodynamic aspects of organic compounds;

- Know the reactivity of the main classes of organic compounds.

- Discussion of all the activities proposed with scientific method and appropriate language.

Furthermore, in reference to the so-called Dublin Descriptors, this course helps to acquire the following transversal skills:

Knowledge and understanding:
- Capacity of inductive and deductive reasoning;

- Ability to rationalize the property-structure-reactivity correlations of organic compounds.

Ability to apply knowledge:

- Ability to apply the acquired knowledge to rationally describe the chemical behavior of organic compounds, including stereochemical aspects;
- Ability to predict the chemical reactivity of organic compounds based on their molecular structure.

Autonomy of judgment:
- Critical reasoning skills;

- Ability to identify the most suitable conditions for the chemical modification of an organic structure.

Communication skills:

- Ability to describe the structure and chemical behavior of organic compounds in oral form, with properties of language and terminological rigor.

Lectures with classroom exercises.

1. Introduction to organic chemistry
The chemical bond in carbon compounds. Formulas. Structure isomerism. Resonance. Hybrid orbitals. Classification of organic compounds based on the structure and functional groups. Acids and bases.
2. Alkanes and Cycloalkanes
Structure. Nomenclature. Sources. Physical properties. Conformational isomerism. Oxidation. Ring tension in cycloalkanes.
3. Stereoisomerism
Chirality. Stereoisomers: Enantiomers and Diastereoisomers. Stereocenters. Optical activity. Polarimeter. Absolute configuration. The R-S convention. Meso compounds:the stereoisomers of tartaric acid.
4. Alkenes
Structure. Nomenclature. Isomerism: cis-trans and E-Z nomenclature. Addition reaction: halogenation; addition of hydrogen halides; addition of water; Markovnikov's rule; hydrogenation. Reaction mechanisms.
5. Alchynes
Structure. Nomenclature. Chemical properties. Acidity of terminal alkynes. Catalytic reduction.
6.Haloalkanes
Structure. Nomenclature. Nucleophilic substitutions. SN1 and SN2 mechanisms. Stereochemistry of nucleophilic substitutions. Effects of the structure of the substrate, of the nucleophile,of the leaving group and of the solvent. beta-Elimination reactions. E2 and E1 mechanisms.
7. Benzene and derivatives
Structure. Nomenclature and properties of benzene and its derivatives. Aromaticity. Resonance energy. Huckel's Rule. Electrophilic aromatic substitution reactions: halogenation; nitration; sulfonation; alkylation and acylation of Friedel and Crafts. Activating and deactivating substituent groups. Reactivity and orientation.
8. Alcohols, Ethers, Thiols and Phenols
Structure. Nomenclature. Hydrogen bond. Acidity and basicity. Reactions of alcohols and phenols.
9. Aldehydes and ketones
Structure. Nomenclature. Nucleophilic additions: addition of reagents of Grignard, of HCN, of alcohols; semiacetal and acetal formation; addition of ammonia derivatives; formation of Schiff bases. Oxidation. Keto-enol tautomerism. Aldolic condensation.
10. Carboxylic acids and derivatives
Structure. Nomenclature. Acidity constants. Esters. Acid hydrolysis, saponification. Claisen condensation. Acid chlorides. Anhydrides. Amides. Nitriles. Hydroxy acids and keto acids. Fat acids and oils. Phospholipids.
11. Amines
Structure. Nomenclature. Physical properties. Basicity.
12. Carbohydrates
Structure. Classification. Series of aldoses and ketosis. Chirality. Optical activity. Fischer projections. Cyclic structures. Anomers. Stereochemical representations. Mutarotation. Structures of the main disaccharides and polysaccharides: Sucrose, Maltose, Cellobiose, Lactose, Cellulose, Starch, Glycogen.
13. Amino acids and proteins

Natural and essential amino acids. Functions: acid and basic properties; peptide bond. Primary, secondary, tertiary and quaternary structure of proteins.

1. William H.Brown e Thomas Poon: "Introduzione alla Chimica Organica";

2. John McMurry "Fondamenti di Chimica Organica" Zanichelli Ed.