ORGANIC CHEMISTRY SUPERIOR

Teachers: 
Credits: 
6
Site: 
PARMA
Year of erogation: 
2020/2021
Unit Coordinator: 
Disciplinary Sector: 
Organic Chemistry
Semester: 
First semester
Language of instruction: 

Italian language

Learning outcomes of the course unit

Knowledge and understanding

At the end of the course the student is expected to:
- have the necessary knowledge to understand stereoselective, stereospecific and asymmetric induction processes
- know the principles of separative techniques and related applications
- know the most suitable methods for determining the enantiomeric composition of a chiral compound
- know the principles of spectroscopy and related applications, in particular:
∙ know the main chiro-optical techniques
∙ be familiar with the principles of 1H NMR variable temperature spectroscopy
- know the methods of structural characterization of organic compounds and materials
- know the correlations between structure and properties of molecules and materials
- know the techniques for organic compound and material synthesis
- know the catalysis, economic efficiency and sustainable technologies
- have knowledge of environmental issues.

Applying knowledge and understanding

At the end of the course the student is expected to:
- know how to apply and predict the relationship between structure and properties of even complex systems;
- know how to discuss different types of organic reactions treated in the course, with attention to the stereochemical course
- be able to discuss and propose different approaches for the functionalization of solid materials, both surfaces and nanomaterials.
- know how to apply the main parameters to evaluate the environmental sustainability of a reaction, based on the knowledge of the basic principles of 'green chemistry'
- apply the necessary knowledge to understand and to predict stereoselective, stereospecific and asymmetric induction processes.

Making judgments

At the end of the course the student is expected to:
- critically evaluate his/her knowledge and skills
- demonstrate independent judgment skills in evaluating and quantifying the experimental results;
- critically evaluate the quality parameters of alternative analytical techniques according to the nature of the experimental problem;
- make judgments that include reflections on important scientific and ethical issues.

Communication skills

At the end of the course the student is expected to be able to:
- communicate in written and verbal form on chemical problems covered by the course using a correct and appropriate language
- support a contradictory on the basis of a judgment developed autonomously on issues inherent to his/her studies;

Learning skills

At the end of the course the student is expected to:
- possess personal skills in logical reasoning and in the critical approach to new problems;
- be able to independently study solutions to complex problems also interdisciplinary, finding the information useful to formulate answers

Course contents summary

Organic stereochemistry: review of the molecular chirality concepts due to center, axis, plane of chirality, elicity as well atropoisomerism. Chirooptical methods: polarimetry; circular dicroism (CD). Study of dynamic phenomena by NMR spectroscopy. Determination of the enantiomeric composition by chromatographic and NMR methods. Stereoselective and stereospecific reactions. 1,2-Concerted rearrangements involving C, O and N atoms. Diastereo- and enantioselective syntheses. Aldolic condensations. Pericyclic reactions. Epoxidation reactions. Sharpless and Jacobsen-Katsuki enantioselective epoxidation. Chirality amplification. Origin of chirality in nature. Chirality and biological effects. Additional organic reactions (e.g. click chemistry). Heterogeneous and supported catalysts. Functionalisation of solid surfaces and nanomaterials.
The twelve principles of the Green Chemistry. Sustainable development and eco-compatibility of chemical processes: heterogeneous catalysis and new reaction media. Introduction to the stucture-reactivity relationship (Hammett equation).

Course contents

Role of the stereochoemistry in nature; chirality and biological effects. Organic stereochemistry: review of the molecular chirality concepts due to center, axis, plane of chirality, helicity. Atropoisomerism and biphenyls. Study of dynamic phenomena by NMR spectroscopy. Time scale in NMR, IR and UV spectroscopies. Conformational analysis by NMR: thermodynamic and kinetic aspects Chirooptical methods: polarimetry; circular dichroism (CD) and its application in configurational and conformational studies (octant rule).
Determination of the enantiomeric composition by chromatographic and NMR methods. Conglomerates. Resolution of racemates, with examples of large scale applications.
Stereoselective and stereospecific reactions. 1,2-Concerted rearrangements involving C, O and N atoms, including stereochemical outcome. Diastereo- and enantioselective syntheses. Stereochemical outcome in aldolic condensations under thermodynamic or kinetic control. Pericyclic reactions: Diels-Alder reactions and sigmatropic reactions.
Epoxidation reactions (with electrophilic or nucleophilic oxidants). Enantioselective epoxidation using Sharpless as well as Jacobsen-Katsuki chiral catalysts. Chirality amplification. Origin of chirality in nature. Additional organic reactions (e.g. click chemistry). Heterogeneous catalysts for organic synthesis. Supported catalysts. Functionalisation of solid supports with (chiral) metal complexes and biomolecules for enantioselective processes. Functionalization of flat surfaces and of nanomaterials.
The twelve principles of the Green Chemistry. Sustainable development and eco-compatibility of chemical processes: heterogeneous catalysis and new reaction media (water, supercritical fluids, ionic liquids). Examples of environmental friendly industrial processes and comparison with traditional ones.
Introduction to the structure-reactivity relationship: Hammett equation, rho and sigma parameters.

Recommended readings

- F. A. Carey, R. A. Sundberg “Advanced Organic Chemistry” Springer;
- E.L. Eliel, S.H. Wilen “Stereochemistry of Organic Compounds” J.Wiley & Sons;
- R.A. Sheldon,I.Arends, U. Hanefeld- “Green Chemistry and Catalysis”, Wiley-VCH; - D.E. De Vos , I.F.J. Vankelecom, P.A. Jacobs - “Chiral Catalyst Immobilization and Recycling”, Wiley-VCH
- - E. V. Anslyn, D. A. Dougherty, "Modern Physical Organic Chemistry", University Science Book, Sausalito, California

• Literature references on various topics will be given to allow deeper study.

Teaching methods

The teaching activity will be carried out through lectures with the aid of slides. The lessons, possibly carried out in person, will also be usable remotely in the ways that the teacher deems most effective. Selected papers from the literature will be discussed and some exercises will be performed.
The slides used during the lessons are available to students on the Elly platform and will be loaded on a monthlyweekly basis. The subscription to the online course is required to download the files containing the slides. In addition, references of original papers are furnished to permit a deeper study.
Both in the case of frontal and remote lessons there will be spaces for interaction with students

Assessment methods and criteria

The oral exam will take place face to face or remotely if the health emergency continues.
At the end of the course the student is expected to be able to:
The assessment of learning will take place through an oral examination. The oral examination consists of a discussion of the topics dealt with during the course.
In particular, the acquisition of a correct stereochemical language will be verified, as well as the understanding the reaction mechanisms leading to stereoselective and enantioselective processes. Knowledge of concerted reactions and of various approaches to functionalise solid (nano) materials will be checked. Green chemistry approaches to synthesis will be discussed.
The oral test is evaluated on a scale of 0-30. The oral test shall be communicated immediately upon completion of the test.
Please note that online registration on the application is compulsory.

Other informations

The teacher is available to the student for any clarifications or
explanations of the topics covered during the course.