B016522 - SPECTROSCOPIC METHODS IN ORGANIC CHEMISTRY

Italian

Aim of the course is the combined and comparative use of spectroscopic techniques for the structural determination of organic molecules. Infrared spectroscopy, nuclear magnetic resonance spectroscopy (NMR, 1H and 13C NMR) and two-dimensional NMR (homonuclear and heteronuclear) and mass spectrometry are discussed, aiming to give students a basic knowledge, together with exercises for systematic analysis and interpretation of IR, NMR and MS spectra for the identification of organic compounds.

1. Hesse Meier
“Metodi spettroscopici nella chimica organica”
EdiSES

2. Robert M. Silverstein, Francis X. Webster, David J. Kiemle
“Identificazione spettrometrica di composti organici”
Casa Editrice Ambrosiana

The course objectives are to illustrate the use of spectroscopic techniques for determination of structure of organic molecules

To take the exam, the exams of the courses of Physical Chemistry and Organic Chemistry I have to be taken

Teaching lessons and exercises concerning the resolution of structures through the various spectroscopy considered.
Lessons transparences and study material provided by the teacher (present in the virtual classroom set up on the Moodle e-learning platform)
Lessons notes.
Teaching tools: light board, e-learning platform Moodle.

- Reception hours:
Every day after appointment
- Address:
Department of Chemistry "Ugo Schiff"
Via della Lastruccia 3-13, 50019 Sesto F.no, Florence
Tel. 055 4573550
e-mail: antonella.capperucci@unifi.it

There are 5 official appeals, 2 in the January-February winter session, and 3 in the summer session, June-September. In addition, there are 3 appeals, in October, November and April (November and April: during periods of teaching silence). In case of failure to pass the exam, students can register for the next first useful appeal. Passing the exams of Physical Chemistry and Organic Chemistry I is a mandatory requirement to be able to take the examination of Physical Methods in Organic Chemistry. The final exam consists of a written exam (time available 2 hours), followed by an oral exam (lasting 50 minutes). The written exam is aimed at ascertaining the learning process in the resolution of an unknown organic structure through the interpretation of the IR, NMR and MS spectra. Passing the written test allows admission to the oral examination. The final grade takes into account the evaluation of the written and oral tests.
The exam is booked through the online booking service.
During the oral examination the understanding of the relationship between the structure of an organic molecule and its spectroscopic properties is further evaluated, through the prediction of the characteristic absorptions in the spectroscopies treated in class, taking into account, for example, implications due to the effect of chirality. , of stereochemistry, of symmetry, of conjugation. In any case, the student's ability to apply the topics and concepts discussed in class to understand and predict the spectroscopic characteristics of the main functional groups is verified.

General principles of infrared spectroscopy, with particular attention to the characteristics of the various functional groups and to the nature of the substituents. The process of infrared absorption; modes of vibration and oscillation; properties of bonds and absorption. Instrumentation. Systematic examination of the spectra of the most important classes of organic compounds. Overview of quantitative analysis. Lambert-Beer Law.
General principles of nuclear magnetic resonance spectroscopy (NMR). Nuclear spin states, nuclear magnetic moment, energy absorption and its effects. Instrumentation. Definition of chemical shift. Shielding constant, local diamagnetic effects, diamagnetic anisotropy. Proton magnetic resonance. Coupling constants, chemical and magnetic equivalence. Types of proton spectra. Simplification of spectra. Decoupling methods. Effect of chirality. Overview of magnetic resonance of Carbon-13. Effect of symmetry on NMR spectra. nOe Effect. Shift reagents. Overview of two-dimensional nuclear magnetic resonance imaging. Pulse technique with Fourier transform. Rotating frame of reference. Interpreation of some homonuclear and heteronuclear 2D spectra: COSY, DQF-COSY, HETCOR, HMQC, HSQC, HMBC, TOCSY, NOESY, Definition of COLOC spectra and INADEQUATE 13C-13C.
General principles of mass spectrometry. Generation, fragmentation and detection of ions. Instrumentation. Electron impact (EI) as the main ionization method. Overview of other ionization methods: chemical ionization (CI), FAB, ESI, MALDI. Types of analyzer: quadrupole and sectors (electrostatic and magnetic). Metastable lions. The mass spectrometer as a gas chromatography detector. Types of rearrangements (retro Diels-Alder, McLafferty). Fragmentations characteristic of the most important classes of organic compounds.