00148 - CHIMICA ORGANICA

Learning outcomes

After learning, the student will have a basic knowlegde of structure, properties and reactivity of the main classes of organic compounds and of some natural organic products. The student will be able to: write and understand the structure of organic molecules; forecast the products and mechanism of simple organic reactions.

Course contents

Electronic structure and hybridation of the carbon atom. Covalent bonds in organic molecules.

Functional groups, nomenclature and representation of organic compounds.

Structure and conformations of alkanes. Ring strain and conformations of cycloalkanes.

Stereochemistry of organic molecules: chirality, enantiomery and diasteroisomery.

Elementary reaction mechanisms. Acids and based. Electropiles, nucleophiles and radicals. 

Main classes of organic compounds and their reactions:

Alkanes, origin, physical properties; combustion. Radicalic halogenations of alkanes;

Haloalkanes, nucleophilic substitution, SN1, SN2, stereochemistry of SN; elimination reaction E1 and E2. Brief survey on organometallic compounds;

Alkenes, Alkynes Structure and isomers of C=C bond. Electrophilic and radicalic addition to C=C double bond, addition of alogenhydric acids, water, alcohols, hydrogen. Radicalic polymerization, principal alkenylic polymers; 

Alcohols, ethers Acidity of alcohols; alkylation of alkoxides; oxidation of alcohols; nucleophilic substitution on alcohols and ethers;

Carbonyl componuds, nucleophilic addition to carbonyls, addition of organimetallic compounds, hydrides, water, alcohols, amines; hydrogenation of carbonyls; oxidation of aldehydes. Basics on enolization, keto-enol tautomery, aldol reaction;

Acylic compounds, carboxylic acids, acyl halides, anhydrides, esters, amides; acidity of carboxylic acids. Nucleophilic acylic substitution, formation and hydrolysis of esters;

Amines, basicity of amines; alkylation of amines, reductive amination of carbonyl compounds;

Aromatic compounds, concept of aromaticity; aromatic electrophilic substitution, halogenations, nitration, sulfonation, Friedel-Crafts reactions. Other aromatics;

Natural products, sugars, structure, stereochemistry, nomenclature; di- and polysaccarides: lipids, fatty acids and triglicerids, surfactants and detergents, siccative oils; aminoacids, structure and stereochemistry, proteinogenic aminoacids; peptidic bond, polypeptides and proteins.

Exercises about all topics above mentioned.

Readings/Bibliography

All the university Organic Chemistry texbooks are, generally, suitable.

Some possible suggestions:

W. H . Brown, C. S. Foote, et al. “Chimica Organica”, EDISES, Napoli

J. McMurry “Fondamenti di Chimica Organica”, Zanichelli, Bologna

P. J. Brice “Chimica Organica”, EDISES, Napoli,

P. Vollahrdt “Chimica Organica”, Zanichelli, Bologna

Teaching methods

Lectures and discussion
Exercises

Assessment methods

Oral exam
Written exam on request

Teaching tools

Videoprojection
Molecular models

Office hours

See the website of Emilio Tagliavini

See the website of Paola Galletti