CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Learning outcomes of the course unit
At the end of the course the student should:
- know the IUPAC nomenclature of aromatic heterocyclic compounds and to apply the IUPAC rules;
- know the structural formula of the main aromatic heterocycles;
- know the synthesis of the aromatic heterocycles explained in the course;
- know the reactivity of the heterocycles tackled during the course and, for every class of compounds, have understood the regioselectivity of the different reactions;
- be able to analyze the chemical behavior of the heterocycles in the presence of given reactants;
- know the acid-base behavior and the tautomeric equilibria (when present) of the heterocycles tackled during the course, and be able to order different heterocycles in reactivity and basicity scales;
- be able to apply the knowledges in analysis and solving simple synthesis and retrosynthesis exercises.
It is necessary to have knowledge of organic chemistry. To access the final examination the student must have passed the Organic Chemistry I exam.
Course contents summary
After the classification and nomenclature of heterocyclic compounds, the course will mainly describe aromatic heterocycles, in particular five- and six-membered monocyclic and benzo-fused systems, dealing with their synthesis, physical-chemical properties, tautomerism, and reactivity.
Textbooks and reference books:
1. D. SICA, F. ZOLLO, Chimica dei composti eterociclici farmacologicamente attivi, Ed. Piccin. 2008.
2. J.A. JOULE, K. MILLS, Heterocylic Chemistry, 5th Edition, Wiley-Blackwell Edition.
3. T. GILCHRIST, Heterocyclic Chemistry, Ed. Longman, 1997.
4. D. T. DAVIES, Aromatic Heterocyclic Chemistry, OUP Ed., Oxford Chemistry Primers, 1992.
Additional teaching material for students:
Pdf files of the lesson slides.
The main part of the course will be dedicated to the explanation of the topics at the blackboard in order to give the students the knowledge about the nomenclature, preparation and reactivity of the main heterocyclic compounds. Some hours will be devoted to exercises that will be carried out with the maximum involvement of the students, with the aim to favor the acquisition of skills and competences at the retrosynthetic analysis and reactivity of heterocyclic compounds.
Assessment methods and criteria
Verification of the learning will be carried out by a written examination. The written examination aims at verifying whether the student has acquired the knowledge and developed the skill in applying this knowledge and understanding in the analysis and resolution of exercises. The examination is 90 minutes long and will contain 10 exercises concerning the nomenclature, propriety, reactivity and synthesis of heterocycles. Every exercise will have the value of 3/30. The exam will be pass with a mark of 18/30.