ORGANIC CHEMISTRY

CHIM/06 - 6 CFU - 1° Semester

Teaching Staff

ROSARIA SALETTI


Learning Objectives

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


Course Structure

Lectures with classroom exercises.



Detailed Course Content

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.



Textbook Information

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

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




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