Learning objectives
The course is aimed at developing knowledge and concepts rooted in the “Propedeutic Organic Chemistry” course, with a particular emphasis on the structure-activity relationship of the main organic compounds.
Prerequisites
To access the final examination, it is necessary to having successfully passed the following examinations: General and Inorganic Chemistry, Propedeutic Organic Chenistry module.
Course unit content
General Aspects.
Recall and in-depth study of the contents acquired in the previous “Propedeutic Organic Chemistry” course. 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, imines and enamines. Alpha-alkylation and alpha-halogenation of enols and enolates. Aldol additions and condensations and variants thereof. Claisen condensations and related reactions. Michael and Mannich addition reactions. Examples of transposition reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: 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.
Full programme
General Aspects.
Recall and in-depth study of the contents acquired in the previous “Propedeutic Organic Chemistry” course. 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, imines and enamines. Alpha-alkylation and alpha-halogenation of enols and enolates. Aldol additions and condensations and variants thereof. Claisen condensations and related reactions. Michael and Mannich addition reactions. Examples of transposition reactions.
Aliphatic domain. Structure, nomenclature, natural occurrence, physical properties, reactivity, and synthesis of the following compound classes: 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.
Bibliography
Recommended texts (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. Autori vari, “Chimica Organica” (a cura di B. Botta), Edi.Ermes, Milano, 2011.
3. J. McMurry, “Chimica Organica”, VIII Edizione, Piccin, Padova, 2012.
4. M. Loudon, “Chimica Organica”, V Edizione, EdiSES, Napoli, 2010.
5. J. G. Smith, "Chimica Organica", McGraw-Hill, Milano, 2007.
6. G.H. Schmid, “Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1997.
Recommended exercize books (choose one of the following):
1. M. V. D’Auria, O. Taglialatela Scafati, A. Zampella, “Guida Ragionata allo Svolgimento di Esercizi di Chimica Organica”, seconda Edizione, Loghia Ed., Napoli, 2011.
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, 2010.
4. S. Cacchi, F. Nicotra, “Esercizi di Chimica Organica”, Casa Editrice Ambrosiana, Milano, 1998.
Other bibliography:
1. J. Clayden, N. Greeves, S. Warren, P. Wothers, “Organic Chemistry”, Oxford Edition, 2001.
2. R. Norman, J.M. Coxon, “Principi di Sintesi Organica”, 2a Edizione Italiana, Piccin Editore, Padova, 1997.
3. R.T. Morrison, R.N. Boyd, “Chimica Organica”, VI Edizione, Casa Editrice Ambrosiana, 1997.
Other teaching material:
Examples of examination exercises of previous years.
Teaching methods
The course is carried out through frontal oral lessons comprising exercises.
Assessment methods and criteria
The final examination consists of a 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 intended to test and confirm the student knowledge on the matter.
Other information
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