Universidad de Jaén

- Theoretical Module : Dissertations about the four instrumental methods (UV, IR, NMR and MS) used routinely by organic chemists for structure elucidation .

Section 1. Introduction to spectroscopy and spectrometry.

Chapter 1. Introduction to spectroscopy. (1.5 hours): Introduction to structural determination. The electromagnetic spectrum. Interaction of matter with electromagnetic radiation: General characteristics. The absorption spectra and emission. Spectrometers and resolution.

Section 2. Absorption spectroscopic techniques.

Chapter 2. Ultraviolet and visible spectroscopy. (2.5 hours): Specific features of ultraviolet spectroscopy (UV) and visible (V). Electronic excitation. Selection rules. Energy absorption: Types of electronic transitions. Chromophores and auxocromos. Instrumentation. Description of a visible-ultraviolet spectrum: component parts and terminology. Conjugated compounds, aromatic.

Item 3. Infrared Spectroscopy (IR). (4 hours): Basics: Vibration of diatomic molecules. Normal modes of vibration of polyatomic molecules. Interaction of matter with infrared radiation. Instrumentation and sample preparation. Infrared absorption spectra, characteristic frequencies. Factors affecting the characteristic frequency of a group. IR spectrum regions and types of bonds, analysis of IR spectrum.


Section 3. Nuclear Magnetic Resonance Spectrometry.

Chapter 4. Basics of Nuclear Magnetic Resonance (NMR). (5 hours): Introduction to NMR: The nuclear spin, spin states and magnetic field. Instrumentation. Chemical shift and factors that modify it. Chemical equivalence. The intensity of the signals. Spin-spin coupling. Chirality and NMR. Dynamic Effects in NMR.

Chapter 5. Advancing Nuclear Magnetic Resonance (NMR). (3 hours): NMR Approach to the "pulses" and the Fourier transform. The relaxation: T1 and T2. NOE effect. ¹³C spectroscopy: chemical shift and intensity, determination of multiplicity. 2D NMR spectroscopy: homonuclear and heteronuclear, types of experiments, how to extract information.

Section 4. Mass spectrometry.
   
Chapter 6. Mass spectrometry (MS). Fundamentals and Applications. (3,5 h): Background: discrimination of charged fragments based on their relationship "charge / mass". The mass spectrometer: overview, ionization chamber, acceleration system, analyzer, detector and recorder. Ionization Techniques: CI, FAB, APCI, ESI, MALDI. Processes occurring inside a mass spectrometer: the fragmentations. The mass spectrum: general description, component parts and terminology. The nitrogen rule. Determination of the molecular formula: exact mass and isotope ratio. Common fragmentations. How to analyze a mass spectrum.


Section 5. Systematic Structural determination of unknown substances.

Chapter 7: Systematic Structural determination of unknown substances. (0,5 h) Combined use of various spectroscopic, spectrometric techniques to solve the structure of a substance.

Practice Module: Experimental multistep synthesis of an organic compound, including the use of separative and spectroscopic techniques for structure elucidation

Seminars Module: There are three separate sections:
-    Resolution of the proposal exercises about the theory, with practical examples for the structure elucidation of organic compounds
-     Software and web resources of utility in this subject.
-    Advanced experimental techniques in organic synthesis

The course is divided in two parts, one dealing with theory of the major instrumental methods used routinely by organic chemists: ultra-violet/visible (UV-VIS), infra-red (IR), nuclear magnetic resonance spectroscopy (NMR), and mass spectroscopy (MS). A concise introduction to the Physics background of each of them, describing how the molecules as well as their fragments interact with electromagnetic radiation will be provided .This information is applied to the determination of chemical structures. The course also includes a simple description of the instrumentation and emphasizes modern methodology throughout, such as the Fourier-transform approach to data analysis.

Each chapter is related with a set of problems to be solved in the seminar lectures to test the understanding of organic spectroscopy.

The second part is related with some practical experiments that the students will carry out in the lab. In these experiments a multistep synthesis of an organic compound is developed. Different experimental and spectroscopic techniques will be used for the setup, separation and structural elucidation of each compound involved in the synthetic pathway.

Students with special educational needs should contact the Student Attention Service (Servicio de Atención y Ayudas al Estudiante) in order to receive the appropriate academic support

Three different aspects will be taken into account for the final mark:

- A final examen to evaluate the degree of knowledge of theoretical-practical concepts. With resolution of practical cases and exercises similar to those done in seminars. (70 %)

- Experimental sessions: evaluation of Report and the going on working in the lab. (15 %)

- Seminars and ongoing work: evaluation of the proposal exercises and practical cases, which will be done individually by each student. (15 %)

TO OVERCOME THE SUBJECT THE LABORATORY PRACTICE MUST BE ATTENDED OBLIGATORY, AND THE CALIFICATION OF THE EXAM SHALL OVERCOME THE 45 %