Advanced organic synthesis. Reaction mechanisms.

- Acquisition of a complete and integrated training of modern strategies in organic synthesis and in the study of reaction mechanisms.
- Simultaneous and complementary learning of the most common reactions and their reaction mechanisms that provide the student with an integral and current vision of these fundamental areas of Organic Chemistry.
- Overview of the experimental methods most commonly used to elucidate the mechanisms of organic reactions.

- Retrosynthetic analysis applied to complex molecules.
- Synthesis of 1,2-,1,3-,1,4- and 1,5-diffunctionalized compounds.
- Formation of carbon-carbon multiple bonds.
- Transition metal-mediated carbon-carbon bond formation.
- Asymmetric synthesis.
- Pericyclic reactions: cycloadditions, sigmatropic transpositions.
- Basic aspects in the experimental determination of the mechanism of a reaction.
- Stereochemistry and reaction mechanisms.
- Chemical kinetics and reaction mechanisms.
- Isotopic effects.
- Linear free energy relationships.
- Catalysis.

BASIC BIBLIOGRAPHY
• E. V. Anslyn, D. A. Dougherty, Modern Physical Organic Chemistry, University Science: Sausalito, CA,2006.
• M. Gómez Gallego, M. A. Sierra, Organic Reaction Mechanisms, Springer-Verlag, 2004.
• R. Bruckner, Organic Mechanisms: Reactions, Stereochemistry and Synthesis. Springer 2010.
• R. E. Gawley, J. Aubé, Principles of Asymmetric Synthesis, 2nd Ed., Elsevier: Oxford, 2012.
• Asymmetric Synthesis, The Essentials, M. Christmann and S. Bräse, Eds. Wiley-VCH: Weinheim, 2007.
• W. Carruthers, I. Coldham, Modern Methods of Organic Synthesis, 4th Ed., Cambridge University Press: Cambridge, 2004.
• J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2nd Ed., Oxford University Press: Oxford, 2012.
• S. G. Warren, P. Wyatt, Organic Synthesis: The Disconnection Approach, 2nd. Ed., Wiley, 2009.
• P. Wyatt, S. Warren, Organic Synthesis: Strategy and Control, Wiley, 2007.

COMPLEMENTARY BIBLIOGRAPHY.
• Enantioselective Organocatalysis: Reactions and Experimental Procedures, P. I. Dalko, Ed., Wiley-VCH: Weinheim, 2007.
• Stereoselective Organocatalysis: Bond Formation Methodologies and Activation Modes, R. Rios Torres, Ed., John Wiley and Sons: New Jersey, 2013.
• Organic Synthesis Workbook, J. A. Gewert, J. Görlitzer, S. Götze, J. Looft, P. Menningen, T. Nöbel, H. Schirock, C. Wulff, Wiley-VCH: Weinheim, 2000.
• Organic Synthesis Workbook II, C. Bittner, A. S. Busemann, U. Griesbach, F. Haunert, W.-R. Krahnert, A. Modi, J. Olschimke, P. L. Steck, Wiley-VCH: Weinheim, 2001.
• R. B. Grossman, The Art of Writing Reasonable Organic Reaction Mechanisms, 2nd Ed. Springer 2003.

Basic and general
- CB6 - Possess and understand knowledge that provides a basis or opportunity to be original in the development and/or application of ideas, often in a research context.
- CB7 - Apply the knowledge acquired and their ability to solve problems in new or unfamiliar environments within broader (or multidisciplinary) contexts related to their area of ​​study.
- CB9 - Communicate conclusions and the knowledge and ultimate reasons that sustain them to specialized and non-specialized audiences in a clear and unambiguous way.
- CB10 - Students should have developed the learning skills necessary to undertake future studies in a way that will be largely self-directed or autonomous.
- CG5 - Students should be well prepared to pursue future doctoral studies in multidisciplinary tasks.
- CG6 - Ability to develop a work in technology companies related to Organic Chemistry
- CG8 - Ability to apply the scientific method and the principles of Organic Chemistry to formulate and solve complex problems.

Cross competences
- CT4 - Apply the concepts, principles, theories or models related to Organic Chemistry to new or little known environments, within multidisciplinary contexts.
- CT6 - Demonstrate learning capacity and autonomous work for the development of their professional life.

Specific competences
- CE1 -To know the most relevant methods and strategies of modern organic synthesis, including stereoselective processes and catalytic processes and be able to design routes for the synthesis of complex organic molecules.
- CE4 - Know and understand the reaction mechanisms commonly accepted in Organic Chemistry and the most common methods available for their determination.

MD1. Theoretical face-to-face classes. Lectures (use of blackboard, computer), complemented with virtual teaching tools.
MD2. Individual or small group tutorials.
MD3. Resolution of practical exercises (problems, test questions, interpretation and processing of information, evaluation of scientific publications, etc.).
MD4. Seminars, problem classes and/or lectures by experts.
MD9. Use of specialized computer programs and internet.
MD10. On-line teaching support (virtual campus).

The class attendance is mandatory.

The evaluation of this subject will be done through continuous evaluation and a final exam.

The final exam will deal with the totality of the contents of the subject and will have a weight of 75%.
The continuous evaluation will have a weight of 25% in the grade of the course, and will consist of four components: a) resolution of problems and practical cases (10%), b) written works and reports (5%), c) oral presentation (papers, reports, problems and cases) (5%) and d) attendance and participation (5%).

CLASSROOM WORK
Theoretical face-to-face classes (expository): 45 h
Interactive seminar classes (elaboration, presentation and discussion of seminars): 22 h
Scheduled tutorials: 3 h
Evaluation and/or exam: 5 h
Total hours of classroom work: 75 h

NON-CLASSROOM WORK
Bibliographic searches and use of databases: 25 h
Test preparation and study: 125 h

TOTAL: 225 h

It is recommended to pay special attention to the mechanism, the synthetic utility and the stereochemistry of the studied reactions. It is also important to review the subjects of other courses on organic chemistry.
It is recommended a continuous follow-up of the course material, to perform weekly exercises and problems proposed, as well as to participate in the preparation and presentation of a topic related to the content of the subject among those proposed by the teacher.