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Syllabus 2018-19 - 10312016 - Synthesis and Structural Determination of Organic Compounds Lab (Laboratorio de síntesis y determinación estructural de compuestos orgánicos)

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  • Level 1: Tutorial support sessions, materials and exams in this language
  • Level 2: Tutorial support sessions, materials, exams and seminars in this language
  • Level 3: Tutorial support sessions, materials, exams, seminars and regular lectures in this language
DEGREE: Grado en Químicas
FACULTY: FACULTY OF EXPERIMENTAL SCIENCES

ACADEMIC YEAR: 2018-19
SYLLABUS
1. COURSE BASIC INFORMATION
NAME: Synthesis and Structural Determination of Organic Compounds Lab
CODE: 10312016 ACADEMIC YEAR: 2018-19
LANGUAGE: English LEVEL: 1
ECTS CREDITS: 6.0 YEAR: 3 SEMESTER: SC
 
2. LECTURER BASIC INFORMATION
NAME: COBO DOMINGO, JUSTO
DEPARTMENT: U128 - QUÍMICA INORGÁNICA Y ORGÁNICA
FIELD OF STUDY: 765 - QUÍMICA ORGÁNICA
OFFICE NO.: B3 - 467 E-MAIL: jcobo@ujaen.es P: 953212695
WEBSITE: -
LANGUAGE: English LEVEL: 1
 
NAME: MELGUIZO GUIJARRO, MANUEL
DEPARTMENT: U128 - QUÍMICA INORGÁNICA Y ORGÁNICA
FIELD OF STUDY: 765 - QUÍMICA ORGÁNICA
OFFICE NO.: B3 - 451 E-MAIL: mmelgui@ujaen.es P: 953212742
WEBSITE: -
LANGUAGE: English LEVEL: 2
 
NAME: SALIDO RUIZ, SOFÍA
DEPARTMENT: U128 - QUÍMICA INORGÁNICA Y ORGÁNICA
FIELD OF STUDY: 765 - QUÍMICA ORGÁNICA
OFFICE NO.: B3 - 465 E-MAIL: ssalido@ujaen.es P: 953212746
WEBSITE: : http://www4.ujaen.es/~ssalido/
LANGUAGE: English LEVEL: 1
 
3. CONTENT DESCRIPTION

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

Chapter 1. Introduction to spectroscopy, the case of UV-VIS spectroscopy  (3 hours): Introduction to structural determination. The electromagnetic spectrum. Interaction of matter with electromagnetic radiation: General characteristics, the  Electronic excitation and  Selection rules in UV-VIS spectroscopy. The absorption spectra and emission, t ypes of electronic transitions; c hromophores and auxocromos.  Spectrometers and resolution. Relation structure and UV absorption, the conjugation and its effect in the spectrum


Chapter 2. 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.

Chapter 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.

Chapter 4. Advancing Nuclear Magnetic Resonance (NMR). (4 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. Chirality and NMR. Dynamic Effects in NMR. 2D NMR spectroscopy: homonuclear and heteronuclear, types of experiments, how to extract information.

Chapter 5. 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.


Chapter 6: 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 (20 h): Experimental multistep synthesis of an organic compound, including the use of a
dvanced experimental techniques in organic synthesis, along with separative and spectroscopic techniques for structure elucidation.


Seminars Module (18 h): 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.

4. COURSE DESCRIPTION AND TEACHING METHODOLOGY

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

5. ASSESSMENT METHODOLOGY

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%

6. BOOKLIST
MAIN BOOKLIST:
  • Experimental organic chemistry. Edition: -. Author: Palleros, Daniel R.. Publisher: New York [etc.]: John Wiley & Sons, cop. 2000  (Library)
ADDITIONAL BOOKLIST:
  • Introduction to organic spectroscopy. Edition: 1st published, repr. Author: Harwood, Laurence M.. Publisher: Oxford [etc.]: Oxford University Press, 2005.
    • Notes: Textbook for theoretical introduction to get the basic knowledge in organic spectroscopy
     (Library)
  • Introduction to spectroscopy: a guide for students of organic chemistry. Edition: 3rd ed. Author: Pavia, Donald L.. Publisher: Fort Worth [etc.]: Harcourt College Publishers, cop. 2001.
    • Notes: Main Textbook to follow this matter both in theoretical and seminar parts, with practical exercises with solutions
     (Library)
  • Spectrometric identification of organic compounds. Edition: 7th ed. Author: Silverstein, Robert M.. Publisher: New York [etc.]: John Wiley and Sons, cop. 2005.
    • Notes: Textbook for theoretical module
     (Library)
  • Organic structures from spectra. Edition: 4th ed.. Author: Field, L. D.. Publisher: Chichester : J. Wiley & Sons, cop.2008..
    • Notes: Practical textbook for seminar parts, with proposal exercises combining UV, IR, MS and NMR in the elucidation of an organic structure
     (Library)
  • Advanced practical organic chemistry. Edition: 2nd ed., repr. Author: Leonard, J.. Publisher: Cheltenham: Stanley Thornes, 1998.
    • Notes: Useful textbook that covers both the main and advanced techniques in an organic laboratory
     (Library)
  • Organic structural spectroscopy. Edition: 2nd ed. Author: Lambert, J. B. et al.. Publisher: Essex: Pearson Education Limited, 2014.
    • Notes: Textbook which deals both with theoretical and seminar parts, with practical exercises with solutions
     (Library)
  • Challenges in molecular structure determination. Edition: -. Author: Reichenbächer, Manfred. Publisher: Heidelberg [etc.] : Springer, cop. 2012.
    • Notes: Textbook for both theoretical and seminar parts, with practical exercises with solutions
     (Library)