Chemical Sciences

FABRIZIO VETICA

Knowledge and ability to understand
The course aims to provide the fundamentals of spectroscopic techniques illustrating their application to the structural characterization of organic molecules. It also aims to give students the experimental aspects related to the synthesis of simple organic molecules and their spectroscopic characterization. The student should demonstrate knowledge of the theoretical foundations of spectroscopic techniques.

Applying knowledge and understanding
The training course is aimed at transmitting the operational skills necessary to fully use the methodological tools to conduct simple organic reactions in the laboratory. In addition, the student must be able to solve problems concerning structural analysis by combining the contribution of the individual techniques illustrated in the course (NMR, MS, IR and UV) in order to determine the structure of organic compounds.


Making judgements
The student must be able to autonomously analyze simple spectra of unknown organic compounds and be able to predict the possible structures suggested by them and, by reasoning, to arrive at the solution. The student must know how to conduct simple organic reactions independently.

Communicatio skills
The student must be able to clearly and appropriately illustrate the approach to the structural determination of simple organic compounds, obtained through the spectroscopies studied, and to know how to expose the aims and potentials of the discipline even in interdisciplinary contexts in the face of specialists and non-interlocutors

Lifelong learning skills
The student must have as objective the comprehension in autonomy of a text, in English too, that deals with topics of general interest proper to the organic chemistry, provided they are relevant to those foreseen by the program of the course; of scientific seminars on various topics of general relevance for organic chemistry; the needs of companies and other professionals in the world of work in terms of knowledge, skills and abilities and possible areas of application.

Knowledge and ability to understand.
The course aims to provide the fundamentals of spectroscopic techniques illustrating their application to the structural characterization of organic molecules. It also aims to give students the experimental aspects related to the synthesis of simple organic molecules and their spectroscopic characterization. The student should demonstrate knowledge of the theoretical foundations of spectroscopic techniques.
Applying knowledge and understanding
The training course is aimed at transmitting the operational skills necessary to fully use the methodological tools to conduct simple organic reactions in the laboratory. In addition, the student must be able to solve problems concerning structural analysis by combining the contribution of the individual techniques illustrated in the course (NMR, MS, IR and UV) in order to determine the structure of organic compounds.
Making judgements
The student must be able to autonomously analyze simple spectra of unknown organic compounds and be able to predict the possible structures suggested by them and, by reasoning, to arrive at the solution. The student must know how to conduct simple organic reactions independently.
Communicatio skills
The student must be able to clearly and appropriately illustrate the approach to the structural determination of simple organic compounds, obtained through the spectroscopies studied, and to know how to expose the aims and potentials of the discipline even in interdisciplinary contexts in the face of specialists and non-interlocutors
Lifelong learning skills
The student must have as objective the comprehension in autonomy of a text, in English too, that deals with topics of general interest proper to the organic chemistry, provided they are relevant to those foreseen by the program of the course; of scientific seminars on various topics of general relevance for organic chemistry; the needs of companies and other professionals in the world of work in terms of knowledge, skills and abilities and possible areas of application.

No prerequisites.

NMR Spectroscopy.
Electromagnetic spectrum. Basic theoretical concepts: the resonance phenomenon. Description of a FT-NMR experiment. Apparatuses and magnets types. Deuterated solvents. Shielding and deshielding phenomena. The chemical shift and its causes : inductive effects, diamagnetic anisotropy. Line width and integral of signals. Chemically equivalent and magnetically equivalent nuclei. Homotopic, enatiotopic, and diastereotopic protons. Spin-spin couplin. First-order spin systems: AX, AMX, AB etc. AA’XX’, AA’BB’, etc systems. Protons on heteroatoms. Hydrogen bond effect on chemical shift. How to simplify a NMR spectrum: using spectrometers with different field values, deuterating, using shift reagents, decoupling, NOE effect. Sample preparationd and spectrum acquisition. 1H NMR spectra and molecular structure. 13C NMR spectroscopy. Chemical shift, coupling. Outline of NMR spectroscopy in chemical kinetics. Dynamic NMR.
IR Spectroscopy. Instruments. Sample preparation. Spectra interpretation. Group frequencies of organic functional groups.
UV-visible Spectroscopy. Electronic transitions. Instruments. Solvent effect on UV-visible spectra, empirical parameters of solvent polarity, bathochromic and ipsochromic effect. Chromophores groups. Electronic transition in ketones and aromatic compounds. Outline of UV-visible spetroscopy in chemical kinetics.
Mass spectrometry. Basic concepts of mass spectrometry. Instruments and spectra registration. Molecular Parent peak, base peak, isotopic peaks. Degree of unsaturations rule. Outline of the more common fragmentations: alpha cleavage, benzylic and allylic cleavage, cleavage of non-activated bonds. Other Ionization methods: CI, DCI, ESI, FAB. Outline of GC-MS technique and of Tandem mass
Practical approach to the NMR, IR, UV-visible and mass spectra interpretation aimed to establish the structure of simple organic compounds.
Students will also perform laboratory experiments concerning simple synthesis of organic compounds. Purification methods: Extraction (solubility and structure, pH effect on solubility, partition coefficient). Distillations (simple and fractionate distillation, azeotropes), Crystallization and filtration. Chromatography (physical principles, TLC and spot detection, column chromatography). Safety in organic chemistry lab. Each laboratory exercise will be preceded by a description in the classroom.

- "Identificazione spettroscopica di composti organici" di R. M. Silverstein e F. X. Webster Casa Editrice Ambrosiana.
- "Metodi spettroscopici nella chimica organica" di M. Hesse, H. Meier, B. Zeeh Casa Editrice EdiSES

The course consists of lectures and laboratory experiences.

Not mandatory

The final exam aims to verify the following learning skills: determination of the structure of organic compounds through the interpretation of their spectra (NMR, mass, IR, UV-vis) discussing the reasoning performed and motivating the choice of the structure, and illustration of the reactions of organic synthesis carried out in the laboratory. The exam consists of passing a written exam consisting in the analysis of a set of spectra of an unknown substance and an oral interview on the topics of the course and laboratory reports, and discussion of the structure identified in the written test. It also consists in the in-depth discussion of one of the reactions conducted in the teaching laboratory.

- Structural determination of an organic compound starting from the analysis of a set of NMR, IR, MS, UV-Vis spectra.
- Theoretical understanding and practical application of the various techniques studied.
- In-depth discussion of a laboratory experience.
- Critical discussion of techniques for purifying an organic compound.