Chemical Sciences

PAOLO LUPATTELLI

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

NMR Spectroscopy: Basic theorical concepts: Electromagnetic spectrum. Resonance phenomenon (spin orientation in a magnetic field, Larmor precession, interaction with electromagnetic waves, quantization, macroscopic magnetization, relaxation T1 and T2, NMR signal and its width). Presentation of a typical NMR experiment. Instrumentation and magnets. Deuterated solvents, Sample preparation.
Chemical shift: 1H-NMR spectrum and molecular structure. Factors affecting chemical shift: hybridization, inductive effects, diamagnetic anisotropy, substituents. Typical shift of common functional groups. Line width and area (integral). Chemical equivalence. Homotopic, enantiotopic and diastereotopic protons.
Spin-spin coupling: Physical principles. Vicinal, geminal and long-range coupling. Karplus relations. First order spin systems: AX, AMX, AB etc. AA’XX’, AA’BB’ systems etc. Magnetic equivalence. Basic concepts on higher order spin systems and typical patterns.
Chemical exchange. Theorical concepts. Protons on heteroatoms. Influence of hydrogen bonding on chemical shift and signal shape. Dynamic NMR. Theorical concepts. Slow and Fast exchange, coalescence. NMR timescale and influence of temperature. Introduction to the use of NMR spectroscopy in kinetics.
Strategies to simplify NMR spectra: use of different instrumentation, deuteration, shift reagents, decoupling, NOE effect.
13C-NMR Spectroscopy. Physical principles, recording of spectra, Chemical shift, coupling.

IR Spectroscopy. Physical principles (vibrational modes and frequencies, assignment of these modes). Instrumentation. Sample preparation. Typical absorbance of common functional groups.

UV-Vis Spectroscopy. Physical principles. Electronic transitions (transition types, wavelengths and intensity). Instrumentation. Chromophore and auxochrome groups. Color and conjugation. Electronic transitions in aromatics and carbonyl compounds. pH effect. Solvent effect. Intro

Mass spectrometry. Key concepts. Ionization methods (EI, CI, FAB, ESI, MALDI). Ion separation methods (magnetic sector, quadrupole, TOF). Recording of spectra. Interpretation of MS spectra: Molecular peak, base peak, isotope peaks. Resolution. Unsaturation rule. Introduction to main fragmentations: alfa cleavage, benzylic and allylic cleavage, McLafferty rearrangement.
Interpretation of NMR, IR, UV-Vis and MS spectra for the identification of organic compounds.

Organic Chemistry Lab. Typical syntheses of organic compounds (Reaction, workup, analysis).
- 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)
- Laboratory practices: Synthesis and purification of simple organic compounds. Safety in organic chemistry lab

- "Identificazione spettroscopica di composti organici" di R. M. Silverstein e F. X. Webster, 3° Edizione, Casa Editrice Ambrosiana, 2016.
- "Metodi spettroscopici nella chimica organica" di M. Hesse, H. Meier, B. Zeeh, 2° Edizione, Casa Editrice EdiSES, 2008

The course consists of lectures and laboratory practices

Attendance at lectures is optional. Attendance at laboratory experiences is mandatory (maximum one absence).

The exam will verify these skills: determination of the structure of an unknown organic compound via interpretation of spectra (NMR, UV, IR, MS) discussing the logic path followed and motivating the proposed structure, in-depth presentation and discussion of the organic reactions involved in the laboratory practices. The exam is divided into two parts: a written exercise (analysis of a set of spectra of an unknown compound to identify its structure) and an oral discussion on the analysis performed in the written exercise, on the course topics and a detailed discussion of one laboratory practice