LEARNING OUTCOMES

The course of Physical Methods in Organic Chemistry aims to provide students with the fundamental knowledge of modern spectroscopic techniques, commonly used in the study of organic molecules in research and control laboratories. The course also aims to provide the ability to identify the most suitable techniques for solving real problems, and to understand UV, IR, MS and NMR spectra of organic molecules. At the end of the course the student will acquire the skills to analyze in depth NMR, IR and MS and UV / Vis spectra, to derive from their combined analysis the structure of unknown compounds, to predict the spectroscopic properties of new compounds, to find spectroscopic data of known molecules through the use of search engines

AIMS AND LEARNING OUTCOMES

At the end of the course the student will acquire:

1. Knowledge and understanding

The student knows and understands the fundamentals, the theoretical principles and the applications of the different spectroscopic techniques: IR, 1H-NMR, 13C-NMR, MS and UV-Vis.

2. Ability to apply knowledge and understanding

The student is able to interpret IR, NMR, MS and UV-Vis spectra of simple pure organic compounds, and is able to choose the spectroscopic technique or the combination of several techniques suitable for different structural investigations. The student is able to apply the known instrumental techniques to new problems that may arise in areas of research or work.

3. Autonomy of judgment

The student is able to integrate the knowledge acquired during the course with those of the chemical-physical strand that characterizes the Degree Course in CTF (study of equilibria, reaction speed, reaction mechanisms, study of intermediates, selectivity, stereochemistry ). The student will be able to acquire from databases and interpret multispectral data useful for the solution of typical problems in research and production areas such as synthesis laboratories, quality control of active principles, laboratories for the analysis of products of natural origin, of complex mixtures of metabolites. These skills are typically stimulated and developed during the performance of spectral interpretation exercises, during lessons and exercises.

4. Communication skills

The student will be able to communicate what he has learned clearly and rigorously. The student is stimulated to interpersonal communication typically during classroom exercises.

5. Learning skills

The student will have developed autonomous learning skills related to spectroscopic techniques through the consultation of databases, bibliographic material and scientific literature available online.

PREREQUISITES

It is essential for the student to ensure that he or she has assimilated the contents of the Organic Chemistry teachings, since only by adequately knowing the fundamental aspects of the subject does it make sense to devote oneself to the study of the more advanced topics found in this teaching

TEACHING METHODS

The course is carried out through lectures, single and group exercises, peer review activities, classroom discussions, solving real problems.

Due to COVID-19 emergency, lectures and exams may take place on TEAMS platform

SYLLABUS/CONTENT

INTRODUCTION: electromagnetic spectrum and electromagnetic radiation, characterization of electromagnetic radiation, electromagnetic radiation and interactions with matter, spectroscopic techniques. Use of databases for the retrieval of spectroscopic data of organic molecules.

INFRARED SPECTROSCOPY: fundamental principles, frequency of infrared absorption and chemical structure. Systematic part: hydrocarbons (alkanes, alkenes, alkynes, aromatics), alcohols, ethers, halides, carbonyl compounds, amines. Combined examples. Instrumentation and recording of spectra, IR spectrophotometer and Fourier transform IR spectrophotometer (FT-IR). Evolution and applications of IR spectroscopy.

NUCLEAR MAGNETIC RESONANCE, NMR (Nuclear Magnetic Resonance): general principles, properties of nuclei, magnetic field and electromagnetic radiation (radiofrequency).

Proton nuclear magnetic resonance (1H-NMR). Reference samples and solvents. Electronic screen and chemical shifts: screen constants in complex molecules. Chemical displacement and magnetic field. Spin-spin coupling and coupling constants. Identification of spin systems. Proton on heteroatoms. Exchange speed. Coupling of protons with other nuclei. Chemical equivalence (symmetry operations) and magnetic. Complex spin systems. Effects due to the presence of a stereogenic element. Coupling between geminal and vicinal protons in rigid systems: correlations of Karplus. Long distance coupling. Decoupling. Overhauser Nuclear Effect (NOE).

Nuclear magnetic resonance of carbon-13: general principles, relative and absolute sensitivity of an NMR experiment, chemical shifts, proton-carbon coupling, decoupled spectra, examples of simple aromatic and non-aromatic compounds, 13C-NMR spectra registered with APT and DEPT.

Two-dimensional magnetic resonance spectroscopy (2D). COrrelation SpectroscopY COSY, HSQC; HMBC, NOESY and TOCSY.

MASS SPECTROMETRY: General principles and instrumentation. Sources (EI, CI, FAB, ESI), analyzers (magnetic, quadrupole), detectors. Analysis of a mass spectrum: molecular ion, fragment ions, general classification of fragmentation reactions. Systematic part: fragmentation reactions of the main classes of organic compounds with exercises.

UV-VIS SPECTROSCOPY: General considerations. Theory and principles of ultraviolet spectroscopy. Lambert-Beer relationship. Electronic transitions. UV instrumentation and solvents. Characteristic absorption of organic compounds.

RECOMMENDED READING/BIBLIOGRAPHY

1) M. HESSE, H. MEIER, R. ZEEH "METODI SPETTROSCOPICI IN CHIMICA ORGANICA" (EdiSES)

2) C. CHIAPPE, F. D' ANDREA "TECNICHE SPETTROSCOPICHE E IDENTIFICAZIONE DI COMPOSTI ORGANICI" (Edizioni ETS)