Download Professor Marina Gatti

.- Organic Chemistry
PROFESSOR MARINA GATTI
COURSE AIMS
Students will gain a logical understanding of the properties and behaviour of
organic molecules through the study of their reaction mechanisms, steric and
electronic effects, resonance etc. and learn to use this knowledge to predict the
products of chemical reactions and the properties of organic molecules.
COURSE CONTENT
Electronic structure and chemical bond. Electron configuration of the atom.
Ionic and covalent bonds. Lewis structures. Octet rule. Formal charge. Resonance
structures. Atomic orbitals. sp3, sp2, sp hybridization. σ and π molecular orbitals.
Structure of methane, ethene and ethyne.
Acids and bases. Brønsted-Lowry acids and bases. Measure of acid and base
strength. The pKa scale. Lewis acids and bases.
Alkanes and cycloalkanes. IUPAC nomenclature system: Nomenclature and
physical properties of alkanes and cycloalkanes. Conformational analysis of
alkanes and cycloalkanes. Cis-trans isomerism in cycloalkanes. Halogenation of
methane: mechanism of radical substitution. Thermodynamic and kinetic aspects of
chemical reactions. Reaction profile: transition state and activation energy.
Reactivity of halogens with respect to radical substitution: comparison between
chlorination and bromination.
Alkenes, alkynes and dienes. Nomenclature and properties of alkenes. Cis-trans
isomerism. E, Z nomenclatures. Heat of hydrogenation and stability of alkenes.
Mechanism and examples of electrophilic addition on the double bond. Stability
and transposition of carbocations. Nomenclature of alkynes. Acidity of terminal
alkynes. Electrophilic addition on the triple bond. Structure of dienes and stability
of conjugated dienes.
Aromatic compounds. Benzene: aromaticity and resonance energy. Nomenclature
of monosubstituted benzenes. Aromatic heterocyclic compounds of biological
interest: pyrrole, furan, thiophene, indole, imidazole, pyridine, pyrimidine, purine..
Overview of polycyclic aromatic hydrocarbons. Mechanism of electrophilic
aromatic substitution. Monosubstituted benzenes: effect of substituents on
substitution rate and orientation.
Stereochemistry. Molecular chirality and enantiomers. R,S convention. Optical
activity. Racemic mixtures. Compounds with two or more stereocentres.
Diastereoisomers. Meso compounds.
Alkyl nucleophilic substitution and elimination reactions. Properties of
haloalkanes. SN2 and SN1 mechanisms: factors influencing the reaction kinetics. E1
and E2 mechanisms. Competition between substitution and elimination.
Alcohols, phenols and ethers. Nomenclature and acid-base properties of alcohols.
Reactivity of alcohols connected with breaking of the R-OH bond: reactions with
halogen-hydride acids and dehydration to alkenes. Reactivity of alcohols connected
with breaking of the RO-H bond: oxidation of primary and secondary alcohols,
nucleophilic behaviour. Comparison of reactivity and acidity of alcohols and
phenols. Quinones and biological oxidation-reductions. Nomenclature and
reactivity of ethers and epoxides.
Amines. Nomenclature and basicity of aliphatic and aromatic amines. Alkylation
of ammonia. Notes on the reaction of aliphatic amines with nitrous acid.
Aldehydes and ketones. Structure of the carbonyl group and nomenclature of
aldehydes and ketones. Nucleophilic addition to a carbonyl group: mechanism in
neutral or basic environment and in acid catalysis. Reduction to alcohols with
hydrides and Grignard reagents. Addition of water and alcohols.
Carboxylic acids and functional derivatives. Structure and nomenclature of
carboxylic acids, acyl halides, anhydrides, esters and amides. Acidity of aliphatic
acids and effect of substituents in α. Nucleophilic acyl substitution: general
mechanism. Reactivity of carboxylic acids and functional derivatives. Reactions of
acyl chlorides, anhydrides, esters, carboxylic acids and amides. Amides of
nicotinic acid and biological oxidation-reductions. Hydrolysis of esters and amides.
Preparation of acyl halides.
Bifunctional compounds. Nomenclature of bifunctional organic compounds with
particular reference to di- and tri-carboxylic acids, hydroxy acids and keto acids.
Reactivity of hydrogens in α to carbonyl C. Acidity of hydrogens in α.
Enolization of aldehydes, ketones and esters. Aldol condensation. Dehydration of
aldols. Claisen condensation.
Fats and oils. Nomenclature and physical characteristics of saturated and
unsaturated fatty acids. Soaps and detergents. Waxes and phospholipids.
Carbohydrates. classification and chirality of monosaccharides. D/L
configuration notation: D-series aldoses and ketoses. Cyclic structure of
monosaccharides: pyranose and furanose forms. Haworth projections and
conformational formulas. Mutarotation. Formation and hydrolysis of glycosides.
Notes on disaccharides and polysaccharides.
Natural -amino acids. Classification, nomenclature and configuration. Acidbase characteristics and titration of an amino acid. Isoelectric point. Peptides.
Nucleic acids. Composition of nucleic acids. Structure of nucleosides and
nucleotides.
READING LIST
W.H. BROWN-C.S. FOOTE-B.L. IVERSON-E.V. ANSLYN, Chimica Organica, 4a ed., EdiSES s.r.l., 2010.
K.P.C. VOLLHARDT-N.E. SCHORE, Chimica Organica, 3a ed., Zanichelli, 2005.
TEACHING METHOD
The course comprises 6 credits for classroom lectures and 1 credit for practical tutorials.
The course includes 12 hours of teaching assistant support.
On-line study materials (http: //blackboard. unicatt. it).
ASSESSMENT METHOD
Final oral examination.
NOTES
Attendance at the tutorial sessions is mandatory.
Professor Marina Gatti will receive students at the times posted.