ORGANIC CHEMISTRY I
Learning outcomes of the course unit
Aim of the Course
The course is aimed at introducing the students into the vast realm of organic chemistry, with a particular emphasis on the structure-activity relationship of the main organic compounds.
The examination of “General and Inorganic Chemistry” must be passed before that of “Organic Chemistry I.
Course contents summary
General Aspects. Origin and development of organic chemistry as a science. Functional groups of the main organic compounds. The carbon atom as a focal element in organic chemistry. Relationships between the structure of an organic compound and its physical and chemical behaviour. Elemental organic analysis. 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 substitutions 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. 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. Synthesis of enols and enolates. Alpha-alkylation and alpha-halogenation of enols and enolates. Aldol additions and condensations and variants thereof. Examples of transposition reactions.
Aliphatic domain. 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.
Aromatic domain. 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.
Recommended tests (choose one of the following):
1. S. Ege, “Chimica Organica: Struttura e Reattività”, Idelson-Gnocchi, 2a Ed. Italiana, Napoli, 2003.
2. G.H. Schmid, “Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1997.
3. W.H. Brown, C.S. Foote, “Chimica Organica”, EdiSES, 2a Ed., Napoli, 1998.
4. J. McMurry, “Chimica Organica”. 1a Edizione Italiana, Zanichelli, Bologna, 1995.
5. H.D. Baker, R. Engel, “Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1995.
Tests for exercizes:
1. T.W.G. Solomons, J.E. Fernandez, “La Chimica Organica Attraverso gli Esercizi”, Zanichelli, Bologna, 1981.
2. S. Cacchi, F. Nicotra, “Esercizi di Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1998.
1. R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a Edizione Italiana, Piccin Editore, Padova, 1997.
2. J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford Edition, 2001.
3. R.T. Morrison, R.N. Boyd, “Chimica Organica”, VI Edizione, Casa Editrice Ambrosiana, 1997.
The course is carried out through oral lessons.
The final examination consists of one written exam and an oral colloquium (only if the written exam has been passed). The written exam deals with the execution of exercises on the synthesis and reactivity of organic compounds, The oral colloquium is intented to test and confirm the student knowledge on the matter.