ADVANCED ORGANIC CHEMISTRY
- Overview
- Assessment methods
- Learning objectives
- Contents
- Full programme
- Bibliography
- Teaching methods
The prerequisites are the course contents of Organic Chemistry 1 and 2.
The exam consists of a 2-3 hour written test with open questions on the three main topics covered and application-type exercises related to static stereochemistry and pericyclic reactions
The course, which is adressed to students of all chemical fields, proposes, through the discussion of different topics, specific to organic chemistry and strongly interdisciplinary, to make students understand:
a) The great importance of the shape of the molecules and of the spatial arrangement of the atoms on their physical and biological properties (static organic stereochemistry)
b) Engineering challenges in the construction of molecules with special dynamic properties related to the presence of mechanical and non-chemical bonds (molecular machines and topological stereoisomers)
c) The rules imposed by the electronic structure of reactive molecules in some transformations, such as pericyclic reactions, of great theoretical and applicative relevance (cycloadditions, electrocyclic reactions, sigmatropic transpositions)
The student is expected to learn new tools that allow him to surprisingly predict certain properties, reactivity and obedience to external stimuli of simple and complex organic molecules.
The course is divided into 3 modules:
a) Stereochemistry: Symmetry operations. 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) Topological Stereoisomers and Molecular Machines: Topological stereoisomers: theoretical approaches and experimental problems in the synthesis of catenans, Moebius strips and trefoil knots
Molecular machines: theoretical principles and applicable examples (10 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. Ene reactions (20 hours)
The course is divided into 3 modules:
a) Stereochemistry: Symmetry operations. 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) Topological Stereoisomers and Molecular Machines: Topological stereoisomers: theoretical approaches and experimental problems in the synthesis of catenans, Moebius strips and trefoil knots
Molecular machines: theoretical principles and applicable examples (10 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)
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.
Copy of part of the slides used during the lessons
The course includes 48 hours of lectures consisting in theoretical lessons and application exercises. The lessons will be conducted with the support of slides.