Unit PHYSICAL METHODS IN ORGANIC CHEMISTRY
- Course
- Chemistry and technology of drugs
- Study-unit Code
- A001806
- Location
- PERUGIA
- Curriculum
- In all curricula
- Teacher
- Claudio Santi
- Teachers
-
- Claudio Santi
- Luana Bagnoli
- Hours
- 72 ore - Claudio Santi
- 12 ore - Luana Bagnoli
- CFU
- 9
- Course Regulation
- Coorte 2021
- Offered
- 2023/24
- 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
- Introduction to spectroscopic methods. The electromagnetic spectrum.
IR spectroscopy. Mass spectroscopy. 1H NMR spectroscopy. 13C NMR Spectroscopy Introduction to spectroscopy, 31P, 19F.
Overhauser Effect: 2D-NMR spectroscopy. Combined spectral data interpretation for structure elucidation. 1CFU will be dedicated to the application of the physical methods to the sustainability of the organic processes. - Reference texts
- Notes and exercises distributed free of charge by the teacher
Silverstein, Webster, Kiemle "Spectrometric Identification of Organic Compounds" Second Edition, Ambrosiana - Educational objectives
- Expected outcomes:
It is the first course of Sporetoscopic Analysis for Organic Molecules.
The main target is to provide students with the basic knowledge the structure elucidation of organic molecules as well as the quantitative composition of organic mixtures using the spectroscopic techniques commonly used in research institutes, chemical / pharmaceutical industries and laboratories for analysis.
The main acquisitions will be
- Basic knowledge of spectroscopic techniques
- fundamental notions on ultraviolet-visible spectroscopy
- fundamental notions on Infrared spectroscopy
- Essential Knowledge on Mass Spectrometry Techniques
- Basic and advanced concepts on Nuclear Magnetic Resonance Spectroscopy
The main skills (understood as the ability to apply acquired knowledge) will be:
-Use the results obtained by ultraviolet-visible spectroscopy for the quantitative determination of a compound or a mixture of compounds bearing a chromophore
-correlate the molecular structure to UV-Vis absorption.
-Use the results obtained by Infrared Spectroscopy to detect the presence of one or more functional groups.
-Use the results obtained by mass spectrometry techniques to calculate the molecular forula of an organic compound and / or to identify the presence of heteroatoms such as Br Cl I P N S Se
-Use the analysis of mass fragmentation to obtain structural information
-interpretation of Nuclear Magnetic Resonance techniques of the carbon proton and other heteronucleus to determine the structure of an organic compound.
-interpretation of bidimensional 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 spectroscopy in combination to assign molecular structures in a unique way. - Prerequisites
- In order to fully understand and apply the topics approached in this Course students must have successfully defended the exams of Physical Chemistry and Organic Chemistry-1 .It is important that the student will be skilled in the use of the IUPAC nomenclature for organic compounds as well as have the fundamental concepts of atomic and subatomic physic with particular regards to the theory of the spectroscopy .
The topics covered in the module will require an adequate knowledge of the concepts of atomic structure , reactivity of functional groups in organic compounds and their stereochemistry . The knowledge of all these matters is a prerequisite for the student who wants to successfully follow the Course - Teaching methods
- The course is organized as follows:
- Frontal lessons that will cover all the subjects of the Course.
- exercises on spectral data interpretation and structures elucidations reading and molecular structure determination.
- examples of problem solving
-two practical section at the instruments - 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 - Learning verification modality
- The exam consist 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
Supports for students with disabilities please visit http://www.unipg.it/disabilita-e-dsa g the 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