In this subject spectrometric methods are described and used

for the elucidation of organic compound structures. For this purpose, both the experiments described in Organic Chemistry II and some more advanced ones are used.

It is convenient to have passed the Organic Chemistry I and Organic Chemistry II courses.

The following skills will be worked on:



MO3CM11: Ability to explain orally and in writing in an understandable way, phenomena and processes related to Chemistry and related subjects, in Basque and/or Spanish and English



MO3CM13: Capability to design and carry out synthesis processes and other experiments, as well as to use appropriate instrumental techniques for different types of chemical problems



MO3CM16: Evaluate, interpret, synthesize, and transmit chemical data and information



MO3CM17: Knowing how to use the tools for the structural determination of organic molecules, properly interpreting the results

1. Nuclear Magnetic Resonance of 1H, 13C and other nuclei. Chemical shift. Coupling. Nuclear magnetic resonance of carbon-13 and other nuclei. Support techniques in the interpretation of NMR spectra. Two-dimensional NMR experiments.



2. Mass spectrometry Spectrum recording. The Nitrogen Rule Resolution. Determination of molecular formulas. Main fragmentation reactions.



3. Infrared spectrophotometry Association between functional groups and absorption bands in the IR spectrum.



4. UV-Vis Spectrophotometry Electronic transitions of interest. Chromophores and auxochromes. Conjugation.



5. Structural elucidation of complex molecules using all the techniques studied.

The methodologies used are the following ones:



• MAGISTRAL

The basis of spectroscopic methods, the data these methods provide us, and the use of these data to determine structure will be the subjaect of these lessons. The teacher will use the most appropriate methods to send information to the students.



• CLASSROOM PRACTICES

The number of GA hours is very high in this subject. Student training is essential to exploit the information that spectroscopic techniques can provide us, and to be able to establish relationships of said data with the structural characteristics of the molecule. The most effective procedure to achieve this is to solve exercises based on reality. With this purpose in mind:



1. Advance exercises will be proposed to solve at home and discuss in class.



2. Group-work exercises to solve in classroom. The questions generated by the group will be clarified with everyone with the teacher's support.



3. Class exercises to be solved individually so that the students are aware of seeing their personal progress.



In practice, in all areas and especially in the determination of organic structures, practice is essential to achieve results, so theory and work during the day will be essential for the acquisition of skills.



SEMINARS



The seminar hours will be used so that:



1. Students prepare in advance a specific topic (such as infrared vibration bands, analysis of tree diagrams of multiples of 1H EMN ...) on which they will solve individually exercises and problems in the classroom time.



2. At the end of the semester the students will carry out in pairs the elucidation and assignment of the signals of a complex molecule using the data provided by the teacher. The strategy followed for determining the molecular structure will be explained and discussed with the classmates during the seminar hours.

• Final Assessment System
• Tools and qualification percentages:
  • Written test to be taken (%): 70
  • Individual works (%): 20
  • Team projects (problem solving, project design)) (%): 10

ORDINARY CALL



CONTINUOUS ASSESSMENT



The final grade will be calculated taking into account the following sections:



1. Written exam: it will consist of theoretical or theoretical-practical questions and solving exercises. It will comprise 70% of the grade. Minimum mark: 4



2. Individual work: it will include the delivery of exercises and completion of questionnaires throughout the course. It will comprise 20% of the grade. Minimum mark: 4



3. Teamwork: will include the delivery and presentation of work and/or exercises carried out in groups. It will comprise 10% of the grade. Minimum mark: 4



In any case, students will have the right to not to follow continuous assessment process.

To do this, students must submit in writing to the teachers responsible for the subject

waiving continuous evaluation, for which they will have a period of 9 weeks.



In the case of continuous assessment, students may waive the call in a

term that, at least, will be up to one month before the end date of the teaching period

of the corresponding subject. This resignation must be presented in writing to the teaching staff

responsible for the subject.





FINAL EVALUATION



Written exam that will consist of questions related to theory and a practical part of solving exercises. It will comprise 100% of the grade. Minimum mark: 5



In the case of final evaluation, the non-presentation to the test set on the official date

Exams will automatically waive the corresponding call.



**********************************************************************************************



IN CASE OF NON FACE-TO-FACE EVALUATION:



The evaluation will be carried out maintaining the means of evaluation specified in the guide and their corresponding percentages. However, in these circumstances the exam will assess the skills acquired in the course using some of the computer tools provided by the eGela platform.



The exam, which will last approximately 180 minutes, will consist of:

1. Online questionnaire through the egela platform (30%)

2. Structural determination problem that must be solved and uploaded to the platform in a fixed time (70%)



The responses to the questionnaire and the problem solving strategy may be required to be argued through a personal interview via BlackBoard Collaborate with the teachers of the subject.



On the other hand, the student must notify the teacher at least one week in advance of their intention to sit for the exam, so that it can be properly prepared.

Written exam that will consist of questions related to theory and a practical part of solving exercises. It will comprise 100% of the grade. Minimum mark: 5



***********************************************************************************************



IN CASE OF NON FACE-TO-FACE EVALUATION:



The evaluation will be carried out maintaining the means of evaluation specified in the guide and their corresponding percentages. However, in these circumstances the exam will assess the skills acquired in the course using some of the computer tools provided by the eGela platform.



The exam, which will last approximately 180 minutes, will consist of:

1. Online questionnaire through the egela platform (30%)

2. Structural determination problem that must be solved and uploaded to the platform in a fixed time (70%)



The responses to the questionnaire and the problem solving strategy may be required to be argued through a personal interview via BlackBoard Collaborate with the teachers of the subject.



On the other hand, the student must notify the teacher at least one week in advance of their intention to sit for the exam, so that it can be properly prepared.

PC computer, internet access and scanner (or smartphone or computer's webcam to take photographs...) will be necessary in case of online classes andor exam.

The printer is not essential but it is useful in order to examine the spectral data.

Basic bibliography

HESSE, M.; MEYER, V; ZEEH, B. ¿Métodos espectroscópicos en Química Orgánica¿, 2ª ed. revisada, Síntesis, Madrid, 2005.

PRETSCH, E.; BÜHLMANN, P.; AFFOLTER, C.; HERRERA, A.; MARTÍNEZ, R. ¿Determinación estructural de compuestos orgánicos. Tablas¿, Masson, Barcelona, 2005

In-depth bibliography

SILVERSTEIN, R. M.; WEBSTER, F.X.; KIEMLE, D. ¿Spectrometric identification of organic compunds¿, 7ª ed., Wiley & Sons, Nueva York, 2005
WILLIAMS, D. W.; FLEMING, I. ¿Spectroscopic Methods in Organic Chemistry¿, 6ª ed., McGraw-Hill, Londres, 2007.
FIELD, L.D.; STERNHELL; S., KALMAN, J. R., "Organic Structures from Spectra", 3ª Edición. Wiley, New York, 2002.
P. Young, ¿Practical Spectroscopy: The Rapid Interpretation of Spectra Data¿, 1st Edition, Brooks/Cole, 2000.

Journals

Organic Syntheses: http://www.orgsyn.org/
The Journal of Organic Chemistry: http://pubs.acs.org/journal/joceah
Organic Letters: http://pubs.acs.org/journal/orlef7
European Journal of Organic Chemistry: http://www3.interscience.wiley.com/journal/27380/home
Tetrahedron: http://www.sciencedirect.com/science/journal/00404020
Organic and Biomolecular Chemistry: http://www.rsc.org/Publishing/Journals/Ob/Index.asp
The Journal of Chemical Education: http://jchemed.chem.wisc.edu/

Web addresses

http://www.chem.ucla.edu/~webspectra/index.html
http://www.dq.fct.unl.pt/qoa/jas/ir.html
http://www.cem.msu.edu/~reusch/VirtualText/Spectrpy/spectro.htm
http://www.cis.rit.edu/htbooks/nmr/inside.htm
http://www.ch.ic.ac.uk/local/organic/nmr.html
http://www.intermnet.ua.es/inteRMNet/
http://www.univ-lille1.fr/lcom/RMN2Dhttp://www.nd.edu/~smithgrp/structure/workbook.html/index1.htm#resum2D_us/index_us.htm
http://www.uam.es/departamentos/ciencias/qorg/docencia_red/qo/l21/rmn.html
http://www.mestrec.com