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

Prerequisites Basic knowledge of General chemistry.

Contents

The Course is composed by two teaching Units.

Unit 1

 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 cyclohexanes.

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.

Haloalkanes, nucleophilic substitution, SN1, SN2; elimination reaction.

Alkenes, Alkynes Structure and isomers of C=C bond. Electrophilic and radicalic addition to C=C double bond, addition of halogenhydric acids, water, hydrogen. The C-C triple bond; reactivity of alynes. Electronic properties of cnjugated polyens;  Radicalic polymerization; the most important 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 water, alcohols, amines; hydrogenation of carbonyls; oxidation of aldehydes. Basics on enolization, keto-enol tautomery, aldol reaction; brief notes on polyesters and polyamides; 

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

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

Unit 2

 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 theuniversity 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

The exam is oral.


It consists in the discussion with the teachers of topics contained in the program of the course. Questions will be asked on general topics that the student will present; during the interview the teachers will direct the student to more specific topics. In addition, small exercises can be proposed on topics of nomenclature, stereochemistry, synthetic steps, selectivity.


The student will be assessed for his/her ability to generally know the topic being discussed and to adequately answer the further questions posed in the interlocution, with particular attention to the relative familiarity with the elementary concepts of organic chemistry.


In special cases, at the student's request, in place of the oral exam, a written test may be performed consisting of 6-10 exercises on the topics of nomenclature, stereochemistry, organic functional groups, simple reaction mechanisms, simple synthetic transformations, classes of natural compounds.

Teaching tools

Videoprojection
Molecular models

Office hours

See the website of Emilio Tagliavini

See the website of Paola Galletti