ADVANCED ORGANIC CHEMISTRY
The prerequisites are the course contents of Organic Chemistry 1 and 2.
The final examination consists in a written text concerning both theoretical questions and the resolution of applicative exercises.
The main objectives of the course are:
a) Investigate the stereochemistry of organic molecules and of their reactions.
b) 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.
c) Provide an overview of the methods utilised to investigate reaction mechanisms
The course is divided into 3 modules:
a) 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 (18 hours)
b) 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)
c) Investigation of mechanisms in Organic Chemistry (intermediates, isotopic labelling, stereochemical evidences, isotopic effects, kinetic evidences). Structure-reactivity correlations (10 hours).
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.
Some additional didactic material will be furnished by the teacher
Lectures