Unit PHYSICAL METHODS IN ORGANIC CHEMISTRY
- Course
- Industrial pharmacy
- Study-unit Code
- A001806
- Location
- PERUGIA
- Curriculum
- In all curricula
- Teacher
- Claudio Santi
- Teachers
-
- Claudio Santi
- Luana Bagnoli
- Hours
- 78 ore - Claudio Santi
- 12 ore - Luana Bagnoli
- CFU
- 8
- Course Regulation
- Coorte 2023
- Offered
- 2024/25
- Learning activities
- Base
- Area
- Discipline chimiche
- Academic discipline
- CHIM/06
- Type of study-unit
- Obbligatorio (Required)
- Type of learning activities
- Attività formativa monodisciplinare
- Language of instruction
- English
- Contents
- The course aims to provide students with basic and applied knowledge of the most commonly used spectroscopic methods in Organic Chemistry. In particular, topics related to: - electromagnetic spectrum - IR spectroscopy - mass spectroscopy - 1H NMR and 13C NMR spectroscopies - hints of spectroscopy , 31P, 19F and 77Se - Overhauser effect - 2D-NMR spectroscopy. The course includes a practical component of the application of spectroscopic techniques to the elucidation of organic structures through the combined interpretation of spectra. 1 CFU will be devoted to the use of physical methods for the sustainability of organic synthesis processes.
- Reference texts
- Handouts and exercises distributed by the lecturer via the UNISTUDIUM platform
Silverstein, Webster, Kiemle "Spectrometric Identification of Organic Compounds" Second Edition, Ambrosiana - Educational objectives
- This course is the first teaching of spectroscopic analysis of organic molecules.
The main objective is to provide students with the basics to deal with the study of the structure of organic molecules as well as the composition such as the quantitative composition of mixtures of organic compounds using spectroscopic techniques normally used in research institutes, chemical/pharmaceutical industries and analytical laboratories.
The main knowledge acquired will be
-Basic knowledge of spectroscopic techniques
-Basic knowledge on Ultraviolet-visible spectroscopy
-Basic knowledge on Infrared spectroscopy
-Basic knowledge of mass spectrometric techniques
-Basic and advanced knowledge on Nuclear Magnetic Resonance Spectroscopy
The main skills (understood as the ability to apply the knowledge acquired) will be:
-use the results obtained from ultraviolet-visible spectroscopy for the quantitative determination of a compound or mixture of chromophore compounds.
-correlate molecular structure to the ability to absorb UV-Vis radiation
-Use the results obtained by Infrared Spectroscopy to detect the presence of one or more functional groups.
-Use the results obtained from infrared spectroscopy to detect the presence of one or more functional groups
-Use the results obtained from mass spectrometry techniques to calculate the brute formula of an organic compound and/or to detect the presence of heteroatoms such as Br Cl I P N S Se
-interpreting the fragmentation of a mass spectrum to derive structural information
-interpretation of Nuclear Magnetic Resonance spectra of the proton of carbon and other heteronuclei to determine the structure of an organic compound.
-interpretation of bidimenctional correlation spectra to assign the structure of complex molecular systems and to determine the spatial geometry of a structure.
-Use the results of UV, IR, MS and NMR spectroscopies in a combined manner to assign molecular structures unambiguously. - Prerequisites
- In order to understand and be able to apply the topics described in the teaching, it is necessary to have successfully passed the Organic Chemistry 1 examination and to have at least attended the Physical Chemistry course. It is important that the student is familiar with the use of the IUPAC nomenclature of organic compounds as well as atomic and subatomic physics with particular reference to the theory of spectroscopic techniques.
Some topics covered in the module require adequate knowledge of the concepts of atomic structure, reactivity of functional groups in organic structures and stereochemistry. Knowledge of these topics is an indispensable prerequisite for the student wishing to follow the course successfully. - Teaching methods
- The course is organised as follows
-Frontal lectures that will cover all the topics of the course.
-Practical exercises on reading spectra and determining molecular structures (at least 30 hours)
During the exercises, problem solving techniques will be applied and group work will be stimulated - Other information
- Exercises will be provided during the course, at the end of the course and before the summer session. Before the other examination sections, the teacher and the entire teaching staff will be available for clarification and explanation.
During the course, 4 hours of supplementary teaching will be used for practical demonstrations to the NMR instrument
Supports for students with disabilities please visit http://www.unipg.it/disabilita-e-dsa g the presentation. - Learning verification modality
- The exam consists in a written test and an oral test:
The written test focus on the elucidation of an organic structure on the basis of experimental data obtained from mass spectrometry, elemental analysis, infrared spectroscopy and proton, carbon and, if necessary, heteronuclear Nuclear Magnetic Resonance spectroscopy mono and two-dimensional. The written test will also include the resolution of an issue relating to the stereochemistry of the molecule. (isomeric ratio, enantiomeric excess, determining the geometry of stereocenters). The written exam has a duration of no more than 120 minutes and is designed to test the student's ability to correctly interpret the experimental results of the spectroscopic techniques studied in the course gaining to the unambiguous determination of the structure of an organic molecule.
The oral exam consist in a discussion lasting about 30 minutes aimed at ascertaining the level of knowledge and understanding reached by the student on the contents theoretical, technical and practical mentioned in the program (UV, IR, NMR, mass spectrometry and Advanced NMR techniques). The oral exam will also evaluate the communication skills of the student, the ability to use language scientifically relevant and capacity in organizing a presentation
- Extended program
- Introduction to spectroscopic methods. The electromagnetic spectrum.
IR spectroscopy:
General techniques, instrumentation and solvents. Theory. Molecular vibrations. Types of vibrations. Active and inactive vibrations. Aliphatic hydrocarbons, olefins and aromatics. Ethers and alcohols. Carbonyl compounds. Amines. Years.
Mass spectroscopy:
Theory and instrumentation. Representations of the mass spectra. Factors governing the fragmentation. Principal modes of fragmentation. Rearrangements. Molecular ions. Fragmentation associated with the main groups (aldehydes, ketones, esters, alcohols, ethers, halides, alkyl aromatics most important heterocyclic compounds). Applications of the mass to a biological problem.
Summary substantial problems in identifying substances and structures on the basis of the corresponding spectroscopic data.
Modern techniques of mass spectroscopy
NMR spectroscopy.
Generalities. Instrumentation. Magnetic properties of nuclei. Theoretical aspects. Relaxation processes. The chemical shift. The spin-spin interactions. Chemical exchange. Variable temperature spectra. Shielding mechanisms. Anisotropy. Ring currents. Correlation tables and their use. Aliphatic hydrocarbons, olefins, and aromatics. Alcohols and other hydroxylated compounds. Amines and amides. Aldehydes, ketones, carboxylic acids. Coupling constants. Systems A2, AB and AX. A3 systems, AB2, ABC, AX2, ABX, AMX. Systems AB3, A2B2, a2x2. Stereochemistry. Karplus rule. Applications of NMR spectroscopy to the solution of stereochemical problems. Double resonance. Special techniques. Problems and exercises. 13C spectroscopy, decoupling techniques and DEPT experiments and APT. Introduction to spectroscopy, 31P, 19F.
Overhauser Effect: chmico physical principles in structural analysis and interpretation.
2D-NMR spectroscopy: Experiments NOSY TOCSY COSY HETCOR
Physical Methods for sustainability: on-line analysis (NIR, IR, NMR). Alternative energy sources (Microwaves, Ultrasounds, mechanochemistry). - Obiettivi Agenda 2030 per lo sviluppo sostenibile
- This teaching contributes to the realization of the UN objectives of the 2030 Agenda for Sustainable Development