. - Organic Chemistry
PROF. LUIGI LUCINI
COURSE AIMS
To develop a logical understanding of the properties and behaviour of organic macromolecules
by learning about their reaction mechanisms, their steric and electronic effects.
COURSE CONTENT
CFU
Electronic structure, chemical bonds, reactivity
Electron configuration, ionic and covalent bonds. Lewis structures. Octet rule.
Formal charge. Resonance structures. Atomic orbitals and hybridization,
molecular orbitals. Brønsted-Lowry & Lewis acids and bases.
Hydrocarbon and aromatic compounds
The IUPAC nomenclature system. Nomenclature and physical properties of
alkanes and cycloalkanes. Conformational analysis of alkanes and cycloalkanes.
Cis-trans isomerism in cycloalkanes. Halogenation.
Nomenclature and properties of alkenes. Cis-trans and E,Z isomerism.
Hydrogenation and stability of alkenes. Electrophilic addition to the double bond.
Nomenclature of alkynes. Acidity of terminal alkynes. Electrophilic addition to
the triple bond. Structure of dienes and stability of conjugated dienes.
Properties of haloalkanes. SN2 and SN1 mechanisms. E1 and E2 mechanisms.
Competition between substitution and elimination. Chirality and enantiomers. R,
S convention. Optical activity. Racemic mixtures. Compounds with two or more
stereocentres. Meso compounds.
Aromatic compounds. Benzene: structure, aromaticity and resonance energy.
Nomenclature of monosubstituted benzenes. Aromatic heterocyclic compounds of
biological interest. Overview of polycyclic aromatic hydrocarbons. Mechanism of
electrophilic aromatic substitution.
Alcohols, amines, carbonyl and carboxyl compounds
Alcohols, phenols and ethers. Nomenclature and properties of alcohols. Reactivity
of alcohols; acidity of alcohols and phenols. Nomenclature and reactivity of
ethers.
Amines. Nomenclature and basicity of aliphatic and aromatic amines. Alkylation
of ammonia.
Aldehydes and ketones. Structure of the carbonyl group and nomenclature of
aldehydes and ketones. Nucleophilic addition to a carbonyl group.
Carboxylic acids and functional derivatives. Structure and nomenclature of
carboxylic acids, alkyl halides, anhydrides, esters and amides. Acidity of aliphatic
acids and α-substituents. Nucleophilic acyl substitution. Difunctional compounds.
Reactivity of α-hydrogens to carbonyl C. Aldol condensation. Claisen
condensation.
Oxidation and reduction of organic compounds.
Exercices
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READING LIST
J. GORZYNSKI SMITH, Fondamenti di chimica organica, 2a ed., McGraw Hill, Milano, 2014.
TEACHING METHOD
Classroom lectures and practical tutorials.
ASSESSMENT METHOD
The exam will be in written and oral. Two written tests will be done:
- one will comprise 5-6 exercises on alkyl hydrocarbons and their reactions, and on conformers, having a
maximum score of 31/31 and taking 60 minutes
- the second will comprise 5-6 exercises on nucleofilic substitution, elimination, aromatic compounds and
electrophilic substitution, having a maximum score of 31/31 and taking 60 minutes
In case the score in each test is positive (18/31 as minimum), then the following oral examination will not
include the topics of the tests. However, it is possible to do the exam even when the written test was
unsuccessful, of course preparing the whole course programme.
The oral exam comprises 2-3 questions (5-6 when the tests were not positive) and will be aimed to verify
the knowledge and wide comprehension of all course topics.
Professor Luigi Lucini is available both before and after lectures in the teachers’ room in Cremona, or at the
Institute of Environmental and Agricultural Chemistry.