ADVANCED ORGANIC CHEMISTRY
The prerequisites are the course contents of Organic Chemistry 1 and 2.
The main objectives of the course are:
a)Provide an overview of the methods utilised to investigate reaction mechanisms
b)Investigate the stereochemistry of organic molecules and of their reactions.
c)Illustrate pericyclic reactions (cycloaddition, electrocyclic and sigmatropic rearrangements reactions) both from a mechanistic point of view, through the study of the frontier orbital symmetry, and from an application point of view.
Programm
The course is divided into 3 modules:
a) Investigation of mechanisms in Organic Chemistry (intermediates, isotopic labelling, stereochemical evidences, isotopic effects, kinetic evidences). Structure-reactivity correlations (10 hours).
b) Chirality. Stereogenic elements. Topism. Prochirality and prostereogenicity. Definition and determination of absolute and relative configuration. Racemates and resolution methods. Stereospecific and stereoselective reactions. Diastereoselective and enantioselective reactions (20 hours)
c) Pericyclic reactions: Correlation Diagrams and Frontier Orbital Theory. Cycloadditions [4 + 2] and [2+2] photochemical and thermal. Diels–Alder reaction: regioselectivity and stereoselectivity. Cycloaddiction reactions, 1.3-dipole, mechanism, regiochemistry, stereochemistry and synthetic examples. Electrocyclic thermal and photochemical reactions. Sigmatropic rearrangements [1, j] general information, sigmatropic rearrangements [3.3]: Cope rearrangement, Claisen condensation, and modified Claisen condensation. (20 hours)
Frontal lectures.
J.Clayden, N.Greeves, S.Warren, P.Wothers Organic Chemistry, Oxford University Press
F.A.Carey, R.J.Sundberg, Advanced Organic Chemistry, Part A and B, Plenum Press.
E.L.Eliel, S.H. Wilen, Stereochemistry of Organic Compounds, Wiley Interscience
Final exam: written resolution of exercises and oral discussion of theoretical aspects