PHYSICAL METHODS IN ORGANIC CHEMISTRY
Learning outcomes of the course unit
Students participating in the course will:
- know the main spectroscopic techniques used by chemists for the structural characterization of organic compounds (knowledge and understanding);
- know the instruments and their operating principle for the acquisition of the different types of spectra (knowledge and understanding);
- know the physical principles of UV, IR, RAMAN, NIR, and NMR (knowledge and understanding);
- understand and be able to analyze in-depth UV, IR, MS and NMR spectra of organic molecules;
- be able to get the structures of unknown compounds starting from the analysis of 1H- and 13C NMR, and 2D NMR spectra (applying knowledge and understanding);
- be able to explain in a clear way the analytical and logical process followed to obtain the structure of an unknown compound (communication skills).
Prerequisites
It is necessary to have knowledge of organic chemistry. To access the final examination the student must have passed the Organic Chemistry I exam.
Course contents summary
The course sets out to illustrate the main spectrometric and spectroscopic techniques used nowadays in the organic chemistry field for characterization and/or structural determination of organic compounds.
The analysis techniques that will be treated during the course are the following ones: elemental analysis, UV-Vis and chiroptical spectroscopy, near- and mid-infrared spectroscopy, Raman spectroscopy, mass spectrometry, mono- and bidimensional Nuclear Magnetic Resonance spectroscopy (1H- and 13C-NMR, and 2D NMR).
Besides the physical principles and the energy transitions involved in every technique, particular attention will be devoted to the analysis of spectra and how to obtain from them information for structural determination of an unknown compound.
Recommended readings
Study guide and solution manual for exercises (at least one of the following to be chosen):
Textbooks (one of the following to be chosen):
1. R. M. SILVERSTEIN, F. WEBSTER, "Identificazione Spettroscopica di Composti Organici", Casa Editrice Ambrosiana, Milano.
2. M. HESSE, H. MEIER, B. ZEEH, “Metodi spettroscopici in Chimica Organica”, EdiSES, Napoli.
Reference books:
1. A. Randazzo, Guida Pratica alla Interpretazione di Spettri NMR, Loghìa, 2018
2.D. L. Pavia, G. M. Lampman, G. S. Kriz, J. R. Vyvyan, Introduction to Spectroscopy, Books/Cole Ed.
3. J. KEELER, Understanding NMR Spectroscopy, John Wiley & Sons Inc, 2010.
4. T. CLARIDGE, High Resolution NMR Techniques in Organic Chemistry, Elsevier, 2008.
5. E. BREITMAIER, Structure Elucidation by NMR in Organic Chemistry - A Practical Guide, Wiley, 2002.
6. J. H. SIMPSON, Organic Structure Determination Using 2-D NMR Spectroscopy - a Problem-based Approach, Academic Pr, 2008.
7. R. EKMAN, J. SILBERRING, A. WESTMAN-BRINKMAL, A. KRAJ, Mass Spectrometry: Instrumentation, Interpretation, and Applications, Wiley, 2008.
Additional teaching material for students:
Pdf files of the lesson slides; examples of exercises given in previous examination sessions.
Teaching methods
Frontal lessons will be used, in order that the students could acquire the knowledge and understanding of the spectroscopic techniques and the skills at analysis of spectra. Exercises at different difficulty levels will be performed, that consist in analysis of spectra of compounds with known or unknown structure. The exercises will be carried out with the maximum involvement of the students with the aim to favor the acquisition of analytical skills, according to the above mentioned objectives of the course.
The slides used by the teacher during the course will be published on Elly at the beginning of the course.
Assessment methods and criteria
Verification of the achievements of the course will be carried out by a written examination followed by an oral one (in case the written exam has been passed).
The written examination takes 3.5 h and consists in two exercises: in the first one the student is required to elucidate the structure of an unknown compound of medium difficulty by analyzing 1H-NMR, 13C-NMR 1H-1H COSY spectra; in the second one it is required to elucidate the structure of an unknown compound of low difficulty by a combined analysis of NMR, IR, MS and UV spectra. During the exam the student must have his own calculator and the tables of chemical shifts, IR absorptions, and mass fragments.
The written examination aims at verifying whether the student has developed the skill in applying the knowledge and understanding in the analysis of spectroscopic data, in fact he has to explain the logical process he has followed for solving exercises. The written examination will be judged sufficient whether the student will show good skills in analyzing spectra and in following correct logical processes in building the structure of the unknown molecule, even if he could not reach the correct structure.
The oral examination aims at verifying the theoretical knowledge of the techniques and instrumentations explained in the course.
The result of examinations is marked in thirtieth. A minimum of eighteen thirtieth is required as a threshold. The final mark is the average of the written and oral examination results.
