ORGANIC CHEMISTRY I
Learning outcomes of the course unit
The course is aimed at introducing the students into the vast and fascinating realm of organic chemistry, with a particular emphasis on the structure-activity relationships of the main organic compounds and on the reaction mechanism interpretation.
The examination of “General and Inorganic Chemistry” must be passed before that of “Organic Chemistry I”.
Course contents summary
Origin and development of organic chemistry as a science. The carbon atom as a focal element in organic chemistry. Functional groups of the main organic compounds. Relationships between the structure of an organic compound and its physical and chemical behaviour. Configurational and conformational isomerism. Conformational analysis of linear and cyclic alkanes. Constitutional isomerism and stereoisomerism. Chirality, enantiomers, diastereoisomers, meso compounds, geometric isomerism. Thermodynamic and kinetic control of organic reactions. Reaction kinetics, activation energy, catalysis. Reaction mechanisms. Resonance in organic compounds. Radical and ionic reactions. Nucleophilic and electrophilic species. Acidity and basicity in organic chemistry. Oxidative-reductive reactions. Monomolecular and bimolecular nucleophilic substitution reactions at saturated carbons. Monomolecular and bimolecular elimination reactions. Main solvents in organic chemistry. Organometallic reagents, Grignard reagents. Electrophilic additions to alkenes. Regioselective, stereospecific, and stereoselective organic reactions. Nucleophilic addition to carbon-oxygen double bond. Nucleophilic substitution at the carbonyl group (Acyl nucleophilic substitution). Brief description of the role of protecting groups in organic synthesis. Qualitative identification of the main functional groups. Carbon-carbon bond-forming reactions. Enols and enolates: alpha-alkylation and alpha-halogenation. Aldol additions and condensations and variants thereof. Examples of transposition reactions.
Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: alkanes, cycloalkanes, alkyl halides, alkenes, alkynes, alcohols, diols, thiols, ethers, epoxides, aldehydes, ketones, carboxylic acids, acyl halides, anhydrides, esters, thioesters, lactones, amides, lactams., imides, nitriles, 1,3-dicarbonyl compounds, alpha,beta-unsaturated compounds, amines, nitro- and nitroso-derivatives, azo-compounds.
Aromaticity. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: benzene, substituted benzenes and, in particular, phenols, aryl halides, and aromatic amines. Structure, nomenclature and reactivity of heterocyclic aromatic compounds.
Recommended books (choose one of the following):
1. W.H. Brown, C.S. Foote, B. L. Iverson, E. V. Anslyn, “Chimica Organica”, IV Edizione, EdiSES, Napoli, 2010.
2. J. G. Smith, "Chimica Organica", McGraw-Hill, Milano, 2007.
3. J. McMurry, “Chimica Organica”, VI Edizione, Piccin, Padova, 2005.
4. M. Loudon, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2010.
5. S. Ege, “Chimica Organica: Struttura e Reattività”, Idelson-Gnocchi, 2a Ed. Italiana, Napoli, 2003.
1. M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, seconda Edizione, Loghia Ed., Napoli, 2009.
2. B. Iverson, S. Iverson, “Guida alla soluzione dei problemi da Brown, Foote, Iverson – Chimica Organica”, 3° Ed., EdiSES, Napoli, 2006.
3. T.W.G. Solomons, C.B. Fryhle, R.G. Johnson, “La chimica organica attraverso gli esercizi”, Seconda Edizione, Zanichelli, Bologna, 1981.
Additional reference books:
1. J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford Edition, 2001.
2. R.T. Morrison, R.N. Boyd, “Chimica Organica”, VI Edizione, Casa Editrice Ambrosiana, 1997.
The course is carried out through oral lessons.
Assessment methods and criteria
Learning is verified by a final examination which is both written and oral.
The final examination consists of a written test and an oral colloquium (only if the written test has been passed).
The written test deals with the solution of exercises on the synthesis and reactivity of organic compounds.
The oral colloquium is intended to test and confirm the student knowledge on the matter.