Identifying Data 2020/21
Subject (*) Advanced Organic Chemistry Code 610G01030
Study programme
Grao en Química
Descriptors Cycle Period Year Type Credits
Graduate 1st four-month period
 Fourth Obligatory 6
Language
Spanish
English
Teaching method Face-to-face
Prerequisites
Department Química
Coordinador
Jimenez Gonzalez, Carlos
 E-mail
carlos.jimenez@udc.es
Lecturers
Jimenez Gonzalez, Carlos
Sarandeses Da Costa, Luis Alberto
 E-mail
carlos.jimenez@udc.es
luis.sarandeses@udc.es
Web
General description Esta materia pretende afondar no coñecemento do alumno sobre as estratexias sintéticas mis modernas na química orgánica da actualidade, con énfase nos aspectos estereoquímicos de reaccións orgánicas. Por iso, discutiranse novos conceptos no estudo estereoquímico dos compostos orgánicos e as súas reaccións, os aspectos fundamentais da análise retrosintética e as estratexias xerais de síntese orgánica. Particularmente veránse os principais tipos de reaccións orgánicas na formación do enlace carbono-carbono e do enalce carbono-heteroátomo. Verase tamén algunhas técnicas avanzadas no laboratorio de Química Orgánica.
Contingency plan 1. Modificacións nos contidos
No haberá cambios

2. Metodoloxías
*Metodoloxías docentes que se manteñen
Todas
*Metodoloxías docentes que se modifican
• As actividades de “sesión maxistral e solución de problemas” manterán o mesmo formato e contidos coa única diferencia de que serán impartidas utilizado Teams ou a plataforma que a UDC poña a disposición da comunidade docente.
• O único cambio abranguera as sesión presenciais da metodoloxía “prácticas de laboratorio” que, no caso de que non poidan ser impartidas de forma presencial serán substituídas por actividades on line dedicadas á obtención e caracterización de compostos organometálicos. O resto das actividades relacionadas con esta metodoloxía poderán ser impartidas de forma sincrónica ou asincrónica utilizando as plataformas de teleformación Moodle e Teams ou outras que a UDC poña a disposición da comunidade.

3. Mecanismos de atención personalizada ao alumnado
– Correo electrónico: permanente.
– Moodle: Diariamente. Segundo a necesidade do alumando.
– Teams: Sesións maxistrais, seminarios, titorías (2-6 h/semán).

4. Modificacións na avaliación
Non haberá modificación nin na metodoloxía nin nos porcentaxes asignados a cada una das metodoloxías.

*Observacións de avaliación:
Manterase a avaliación tal y como figura en la guía docente. A única diferencia será na canle utilizada para as probas que pasará a ser Teams ou Moodle ou unha combinación das mesmas
5. Modificacións da bibliografía ou webgrafía
Non hai modificacións da bibliografía.

Study programme competencies
Code Study programme competences
A1 Ability to use chemistry terminology, nomenclature, conventions and units
A4 Knowledge of main types of chemical reaction and characteristics of each
A6 Knowledge of chemical elements and their compounds, synthesis, structure, properties and reactivity
A9 Knowledge of structural characteristics of chemical and stereochemical compounds, and basic methods of structural analysis and research
A10 Knowledge of chemical kinetics, catalysis and reaction mechanisms
A14 Ability to demonstrate knowledge and understanding of concepts, principles and theories in chemistry
A15 Ability to recognise and analyse new problems and develop solution strategies
A17 Ability to work safely in a chemistry laboratory (handling of materials, disposal of waste)
A19 Ability to follow standard procedures and handle scientific equipment
A20 Ability to interpret data resulting from laboratory observation and measurement
A21 Understanding of qualitative and quantitative aspects of chemical problems
A26 Ability to follow standard laboratory procedures in relation to analysis and synthesis of organic and inorganic systems
B2 Effective problem solving
B3 Application of logical, critical, creative thinking
B4 Working independently on own initiative
C1 Ability to express oneself accurately in the official languages of Galicia (oral and in written)

Learning aims
Learning outcomes Study programme competences
Further knowledge of the most important principles of stereochemistry and conformational analysis of organic compounds A1
A9
 B2
 C1
Be able to predict and explain the stereochemistry evolution of chemical reactions A1
A9
Possess knowledge of the main features, the main explanatory theories and mechanisms of the main reactions of C-C bond and C-heteroatom bond formation A1
A4
A10
A14
A15
A21
 B2
 C1
Possess knowledge of the interconversion methods of the main functional groups A1
A4
A6
A14
 B2
B3
Possess knowledge of the main objectives in organic synthesis, the main strategies of synthesis and the retrosynthetic analysis A1
A4
A14
 B2
Possess knowledge of some advanced techniques in the research laboratory of Organic Chemistry A17
A19
A20
A26
 B2
B3
B4

Contents
Topic Sub-topic
Chapter 1. Stereochemistry and conformational analysis Static and dynamic stereochemistry. Stereoselective and stereospecific chemical reactions (chemo-, regio- and stereoselective/specific reactions).
Conformational analysis: conformational effects on reactivity.
Chapter 2. Pericyclic reactions Introduction: characteristics of pericyclic reactions and theoretical approaches. Electrocyclic, Cycloaddition reactions and sigmatropic rearrangements.
Chapter 3. Free-Radical reactions Generation and stability of free radicals. Main free-radical reactions.
Chapter 4. Generation of carbon-carbon bond by enols and enolates. Alkylation, acylation and conjugate addition of enols and enolates
Chapter 5. Generation of carbon-carbon bond by organometallic compounds Organometallic reagents to make carbon-carbon bonds. Reactions involving transition metal complexes.
Chapter 6. Generation of carbon- heteroatom bonds Generation of carbon and oxygen, nitrogen, halide and sulfur bonds.
Chapter 7. Functional group interconversion reactions. Main Functional group interconversion reactions Functional group interconversions through reduction and oxidation reactions.
Chapter 8. Protective groups in organic synthesis The role of protective groups in organic synthesis. The concept of orthogonal sets. Hydroxyl, diols, aldehyde and ketone carbonyl, carboxylic acid and amine protecting groups.
Chapter 9. Retrosyntetic analysis. Synthetic analysis and planning. Retrosyntetic analysis methodology. Types of transformations: disconnections, connections, functional group interconversion, addition and removing functional groups. Economic issues in retrosyntetic analysis. Illustrative synthesis. s

Planning
Methodologies / tests Competencies Ordinary class hours Student’s personal work hours Total hours
Introductory activities A14 1 0 1
Guest lecture / keynote speech A1 A4 A6 A9 A10 A14 25 62.5 87.5
Problem solving A15 A21 B2 B3 B4 C1 9 18 27
Laboratory practice A17 A19 A20 A26 10 15 25
Mixed objective/subjective test A1 A4 A6 A9 A10 A14 B2 B3 C1 4 4 8
 
Personalized attention 1.5 0 1.5
 
(*)The information in the planning table is for guidance only and does not take into account the heterogeneity of the students.

Methodologies
Methodologies Description
Introductory activities An introduction to the subject will be presented to the students where the tasks to be performed along the course and the methodologies, assessment methods and the most relevant literature will be explained. It will be held the first day.
Guest lecture / keynote speech It is planned to carry out 25 sessions of lectures in one group where the theoretical contents of the subject together with relevant illustrative examples will be presented. It will consist mainly of Power Point presentations. Students will have copies of all the presentations via the Moodle application, so that students can prepare them before classes. Interactive student participation will be encouraged at all times.
Problem solving It is planned to carry out 9 problem seminar sessions in small groups where students will solve the problems elaborated by the teacher. Students will have in advance notice of such problems through the Moodle application. These seminars will also be used to solve any doubts that arise during the theoretical classes
Laboratory practice It is planned to carry out three experimental working sessions in which students will have to perform the experiments scheduled. The students will have the procedure and information about such experiments in advance through the Moodle application, so that they can prepare them before the start of the experiment at the laboratory. The student will have to demonstrate the know-how of the experiment before entering the laboratory. They have to elaborate a laboratory notebook which has to be given to the teacher at the end of the experimental work.
Mixed objective/subjective test A final exam have to be done by the student on the dates established by the Faculty Board. Additionally, there is no mandatory midterm exam which will be eliminatory, so that students who pass this test does not need to be tested by that part at the final exam.The aim of these exams will be evaluate the knowledge and skills acquired by students.

Personalized attention
Methodologies
Problem solving
Laboratory practice
Description
This activity will mainly focus on resolving the doubts that may arise when students are trying to solve individually the problems. It will take place in the timetable of tutorials available to the teacher.
In addition, this personalized attention will take place in interviews that the student has to perform before carrying out the experiments scheduled practices
Part-time students or students with special academic permission (according to the rules of the UDC): The same evaluation criteria listed above are applied, but it´s not mandatory to attend classroom lectures. It is compulsory to attend laboratory practical sessions. It will be tried to fit the dates to the student's availability.

Assessment
Methodologies Competencies Description Qualification
Problem solving A15 A21 B2 B3 B4 C1 Student attendance at these seminar classes will be evaluated and their active participation will be assessed by questioning both in the classroom and through email. They will also be evaluated in the resolution of the problems at the seminars. 15
Laboratory practice A17 A19 A20 A26 Firstly, students will be evaluated through a personal interview before they start each experiment. Then the student work at the laboratory will be evaluated from the point of view of organization, management skills to handle all chemicals, equipment and apparatus with care. Finally, the laboratory notebook that student will submit at the end of the experiments will be also evaluated. The attendance and pass these experimental classes are a necessary condition to pass this subject. Attendance at these experimental classes avoids to be considered as not presented. 15
Mixed objective/subjective test A1 A4 A6 A9 A10 A14 B2 B3 C1 Students will have to solve similar problems in the written exams to those done at the seminar classes. There are two exams: the first one or non compulsory partial exam will take place in about half of semester and the final exam to be held on a fixed date on the calendar established by the Faculty Board. The partial exam is not compulsory and is eliminatory, so that students who pass it, they do not have to be evaluated from this part at the final exam. 70
 
Assessment comments
Students must attend all experimental laboratory classes in order to pass this subject.
They must reach at less a 45% for each evaluation items (including both partial exams if the student does not take the global final exam) and they must reach equal to or greater than 5 points average rating. An essential requirement to
pass the subject is to pass the experimental laboratory clases.

A student shall be considered “not presented” when he is not attend the experimental
laboratory classes and he is not present at the final exam.
Students will keep the rates from experimental
laboratory classes and from the seminars at the second opportunity in
July. This new exam will be held on dates determined by the Faculty Board and
the qualification will replace the one obtained in January.

Students at the second opportunity may only be eligible for honors if
the maximum number of them for this subject, according to the academic regulations, has not been covered in full at the first opportunity. In the following academic courses, students will have to perform all activities that are scheduled for that course.
The student who has not passed the laboratory practices will have to perform a test in the laboratory where he will perform the repetition of a part that will be indicated by the teacher. He must pass this test as an essential condition to pass the matter in that second opportunity.

Part-time students or students with special academic permission (according to the rules of the UDC): The same evaluation criteria listed above are applied, but it´s not mandatory to attend classroom lectures. It is compulsory to attend laboratory practical sessions. It will be tried to fit the dates to the student's availability.

Sources of information
Basic Carda, M., Marco, J.A., Murga, J., Falomir, E. (2010). Análisis retrosintético y síntesis orgánica. Castellón de la Plana, Universitat Jaume I
Quiroga Feijóo, M. L (2007). Estereoquímica: conceptos y aplicaciones en química orgánica. Madrid, Síntesis
Harwood, L. M.; Moody, C. J.; Percy, J. M. (1999). Experimental Organic Chemistry. Standard and microscale 2º Ed.. Oxford: Blackwell Science
Clayden, J.; Greeves, N.; Warren, S.; Wothers, P., (2012). Organic Chemistry. Oxford, University Press
McMurry, J. (2000). Química Orgánica. México. Thomsom
Ege, S. (1997). Química Orgánica: Estructura y reactividad. Barcelona. Reverté

Complementary Carey, F. A.; Sundberg, R. J. (2007). Advanced Organic Chemistry 5º Edición. New York: Springer
Smith, M. B.; March, J (2007). March’s Advanced Organic Chemistry 6º Ed.. New York: Wiley
Norman, R. O. C.; Coxon, J. M. (1993 (2001 imp.)). Principles of Organic Synthesis. Cheltenham (RU): Nelson Thornes
Carda, M., Rodríguez, S., González, F., Murga, J., Falomir, E., Castillo, E. (1996). Síntesis Orgánica. Resolución de problemas por el método de la desconexión. Castellón de la Plana: Universitat Jaume I
Eliel, E. L., Wilen, S.H. (1994). Stereochemistry of organic compounds. New York : John Wiley & Sons


Recommendations
Subjects that it is recommended to have taken before
Organic Chemistry 1/610G01026
Organic Chemistry 2/610G01027
Intermediate Organic Chemistry/610G01028
Experimental Organic Chemistry/610G01029
Chemistry Laboratory 2/610G01032

Subjects that are recommended to be taken simultaneously

Subjects that continue the syllabus
Medicinal Chemistry/610G01040
Final Dissertation/610G01043

Other comments


(*)The teaching guide is the document in which the URV publishes the information about all its courses. It is a public document and cannot be modified. Only in exceptional cases can it be revised by the competent agent or duly revised so that it is in line with current legislation.