Guías Docentes Electrónicas
1. General information
Course:
AMPLIFIED ORGANIC CHEMISTRY
Code:
57323
Type:
CORE COURSE
ECTS credits:
6
Degree:
409 - CHEMISTRY
Academic year:
2022-23
Center:
1 - FACULTY OF SCIENCE AND CHEMICAL TECHNOLOGY
Group(s):
20  23 
Year:
3
Duration:
C2
Main language:
Spanish
Second language:
Use of additional languages:
Some bibliography in English
English Friendly:
Y
Web site:
Bilingual:
N
Lecturer: ANGEL DIAZ ORTIZ - Group(s): 20  23 
Building/Office
Department
Phone number
Email
Office hours
S. Alberto Magno, 2ª planta
QUÍMICA INORG., ORG., Y BIOQ.
3461
angel.diaz@uclm.es
Monday, 10-12 am; Tuesday, 10-12 am; Thursday, 11-13 h.

Lecturer: ENRIQUE DIEZ BARRA - Group(s): 20  23 
Building/Office
Department
Phone number
Email
Office hours
San Alberto Magno
QUÍMICA INORG., ORG., Y BIOQ.
3435
enrique.diez@uclm.es

Lecturer: MARÍA VICTORIA GÓMEZ ALMAGRO - Group(s): 20  23 
Building/Office
Department
Phone number
Email
Office hours
IRICA
QUÍMICA INORG., ORG., Y BIOQ.
6732
MariaVictoria.Gomez@uclm.es

Lecturer: MARIA ANTONIA HERRERO CHAMORRO - Group(s): 20  23 
Building/Office
Department
Phone number
Email
Office hours
Irica
QUÍMICA INORG., ORG., Y BIOQ.
6657
mariaantonia.herrero@uclm.es

Lecturer: SONIA MERINO GUIJARRO - Group(s): 20  23 
Building/Office
Department
Phone number
Email
Office hours
San Alberto Magno, 1ª planta
QUÍMICA INORG., ORG., Y BIOQ.
3495
sonia.merino@uclm.es

Lecturer: JULIAN RODRIGUEZ LOPEZ - Group(s): 20  23 
Building/Office
Department
Phone number
Email
Office hours
San Alberto Magno, 1ª planta
QUÍMICA INORG., ORG., Y BIOQ.
3462
julian.rodriguez@uclm.es

Lecturer: ANA SANCHEZ-MIGALLON BERMEJO - Group(s): 20  23 
Building/Office
Department
Phone number
Email
Office hours
Edificio San Alberto Magno
QUÍMICA INORG., ORG., Y BIOQ.
3407
ana.smigallon@uclm.es

Lecturer: JUAN TEJEDA SOJO - Group(s): 20  23 
Building/Office
Department
Phone number
Email
Office hours
S. Alberto Magno
QUÍMICA INORG., ORG., Y BIOQ.
3460
juan.tejeda@uclm.es

2. Pre-Requisites

It is recommended to have taken and passed the modules/subjects Organic Chemistry I (Química Orgánica I) and Organic Chemistry II (Química Orgánica II).

3. Justification in the curriculum, relation to other subjects and to the profession

The subject Organic Chemistry is part of the module Fundamentals of Chemistry (Fundamentos de Química) of the Chemistry Degree. The objectives of this subject are to explain concepts and basic knowledge of Organic Chemistry; to show evidence that supports those said concepts; to use them to solve chemical problems; and to prove that this subject evolves quickly and plays an important role in modern technological developments of different fields, such as biology and materials science, being a crucial part of everyday life aspects.

The natural and organic products are studied in the course ‘Ampliación de Química Orgánica’. The chemical reactions that all the living beings experiment implicate the primary metabolites of the four compounds that are essential to life: carbohydrates, lipids, proteins and nucleic acids. Nevertheless, there are other compounds that are not vital, but they usually contribute to the survival, known as secondary metabolites.

The course aims to study the reactivity of these compounds as well as to apply the previously acquired knowledge and concepts to the two main problems caused by the chemistry of natural products: the structural determination and their synthesis methods. Additionally, there will be included the isolation of natural products from an experimental point of view.


4. Degree competences achieved in this course
Course competences
Code Description
CB02 Apply their knowledge to their job or vocation in a professional manner and show that they have the competences to construct and justify arguments and solve problems within their subject area.
E01 Understand and use chemical terminology, nomenclature, conventions and units
E03 Handle chemicals safely and with respect to the environment
E06 Know the structural properties of chemical compounds, including stereochemistry, as well as the main structural research techniques
E16 Plan, design and develop projects and experiments
G01 Know the principles and theories of Chemistry, as well as the methodologies and applications characteristic of analytical chemistry, physical chemistry, inorganic chemistry and organic chemistry, understanding the physical and mathematical bases that require
G02 Be able to gather and interpret data, information and relevant results, obtain conclusions and issue reasoned reports on scientific, technological or other problems that require the use of chemical tools
G03 Know how to apply the theoretical-practical knowledge acquired in the different professional contexts of Chemistry
G04 Know how to communicate, orally and in writing, the knowledge, procedures and results of chemistry, both specialized and non-specialized
T03 Proper oral and written communication
T11 Ability to obtain bibliographic information, including Internet resources
5. Objectives or Learning Outcomes
Course learning outcomes
Description
Encourage and promote in the student all those values ¿¿and attitudes inherent to scientific activity.
Know the main aspects of the terminology and nomenclature in Organic Chemistry
Recognize the main reactive intermediates and the influence of stereoelectronic effects on their stability and reactivity
Know how to apply the knowledge of Organic Chemistry to the solution of synthetic and structural problems
Know the main preparation methods and the reactivity of the main organic functional groups and relate it to its structure
Know the basic principles of Organic Chemistry.
To ensure that the student is able to search and select information in the field of Organic Chemistry and that he / she is capable of processing and presenting it adequately both orally and in writing, developing his / her synthesis capacity, being critical and objective
To develop in the student the capacity of initiative to pose and solve concrete problems of Organic Chemistry, as well as to interpret the obtained results
Develop your ability to work as a team.
Acquire the necessary practical training to apply it in your professional life. Know the main methods of isolation, purification and characterization of organic compounds
Acquire the ability to handle chemical reagents and organic compounds safely.
Acquire an awareness of environmental protection developing the idea that Organic Chemistry should be used to improve the quality of life.
Learn to work autonomously in a laboratory and know how to interpret the experimental results obtained.
Know the stereochemistry of organic compounds and the stereoselectivity of the main reactions.
Know the structure of the main organic functional groups
Know the structure and function of organic natural products.
Know the utility of the spectroscopic techniques in Organic Chemistry
Additional outcomes
Not established.
6. Units / Contents
  • Unit 1: AMINO ACIDS, PEPTIDES AND PROTEINS: Classification. Stereochemistry. Acid-base behavior. Isoelectric point. Analysis of amino acids. Synthesis methods. Enantioselective synthesis. Peptides. Determination of peptide structure: amino acid analysis. Sequence analysis. Analysis of terminal groups: N-terminal and C-terminal. Selective hydrolysis of peptides. Peptide synthesis strategy. Protection of the amino group. Protection of the carboxyl group. Activation and coupling. Peptide bonds formation. Peptides synthesis in solid phase. Merrifield method. Secondary structure of peptides and proteins. Tertiary structure. Coenzymes. Quaternary structure of proteins. Hemoglobin.
  • Unit 2: CARBOHYDRATES AND NUCLEIC ACIDS: Introduction. Classification. Fischer projections. D-L notation system. Aldoses and ketoses. Rosanoff classification. Cyclic forms: Furanoses, pyranoses. Mutarotation. Anomeric effect. Glycosides. Disaccharides. Polysaccharides. Cell surface glycoproteins. Reactivity of monosaccharides. Reaction with phenylhydrazine. Reduction. Oxidation. Reactions of epimerization, isomerization and retroaldol degradation. Reaction with acid. Formation of thioacetals. Reaction with carbonyl compounds. Chain extension. Aldose degradation reactions. Nucleic acids: nucleosides, nucleotides, nucleic acids.
  • Unit 3: METABOLITES DERIVED FROM ACETATE: Acetylcoenzyme A. Fatty acids, fats and waxes. Biosynthesis of fatty acids. Phospholipids. Prostaglandins. Thromboxanes. Leukotrienes. Terpenes. Isoprene rule and classification of terpenes. Biosynthesis of terpenes. Mevalonic acid route. Linear, monocyclic and bicyclic terpenes. Steroids: structure. Biosynthesis of cholesterol. Carotenoids: structure. Chemistry of vision.
  • Unit 4: OTHER SECONDARY METABOLITES: Polyphenols. Shikimic acid route. Galotanines. Hydroxycinnamic acids. Coumarins. Polyketides route. Naphthoquinones. Anthraquinones. Tetracyclines. Flavonoids. Isoflavonoids. Alkaloids. Alkaloids derived from ornithine and lysine. Alkaloids with pyrrolidine and piperidine structure. Alkaloids with pyrrolizidine and quinolizidine structure. Alkaloids with pyridine structure. Alkaloids derived from phenylalanine and tyrosine. Alkaloids derived from tryptophan: indole alkaloids. Alkaloids derived from purines.
7. Activities, Units/Modules and Methodology
Training Activity Methodology Related Competences ECTS Hours As Com Description
Class Attendance (theory) [ON-SITE] Lectures E01 E06 G01 0.64 16 N N
Class Attendance (practical) [ON-SITE] Practical or hands-on activities E01 E03 E06 E16 G01 T11 1.24 31 Y Y Laboratory activity to acquire the practical skills and competences included in the subject.
Workshops or seminars [ON-SITE] Problem solving and exercises CB02 E01 E06 G02 G03 G04 0.32 8 Y N
Group tutoring sessions [ON-SITE] Combination of methods CB02 E01 E06 G02 G03 G04 0.04 1 Y N
Study and Exam Preparation [OFF-SITE] Self-study G02 T11 2.8 70 N N
Other off-site activity [OFF-SITE] Problem solving and exercises G02 T11 0.8 20 N N
Progress test [ON-SITE] Combination of methods CB02 E16 G02 G03 G04 T03 0.08 2 Y N
Final test [ON-SITE] Combination of methods CB02 E16 G02 G03 G04 T03 0.08 2 Y Y Learning activity in which the student must demonstrate the level of achievement of the competences included in the subject.
Total: 6 150
Total credits of in-class work: 2.4 Total class time hours: 60
Total credits of out of class work: 3.6 Total hours of out of class work: 90

As: Assessable training activity
Com: Training activity of compulsory overcoming (It will be essential to overcome both continuous and non-continuous assessment).

8. Evaluation criteria and Grading System
Evaluation System Continuous assessment Non-continuous evaluation * Description
Assessment of problem solving and/or case studies 15.00% 0.00% It will be positively evaluated the resolution of problems/exercises as well as in class participation. In addition, the student may increase their final grade by completing the exercises handed over by the professor.
Progress Tests 60.00% 0.00% There will be two 2-hours mid-terms to evaluate the learning of the student.
Laboratory sessions 25.00% 25.00% The practical credits will be marked together during the diary lab work where there will be taken into account several aspects, such as dexterity, order, capacity for initiative¿ Additionally, there will be two exercises related to the practices in the final exam.
Final test 0.00% 75.00% There will be a final exam of the module. Nonetheless, the students that have passed the mid-terms would be able to avoid taking this final test.
Total: 100.00% 100.00%  
According to art. 6 of the UCLM Student Evaluation Regulations, it must be provided to students who cannot regularly attend face-to-face training activities the passing of the subject, having the right (art. 13.2) to be globally graded, in 2 annual calls per subject , an ordinary and an extraordinary one (evaluating 100% of the competences).

Evaluation criteria for the final exam:
  • Continuous assessment:
    It is recommended to come to class, however it is not compulsory.
    Attendance to practices is compulsory and, besides, in order to pass the subject it is an essential requirement to obtain at least 40% of the mark of the practical work.
    THE SUBJECT WOULD ONLY BE PASSED JUST WITH THE MID-TERM IF THE MARK OBTAIN IN IT IS AT LEAST A 4. Otherwise, the student will have to take a final exam of the whole subject (it will count as the 60% of the final grade).
    In order to pass the subject, the weighted mark of the evaluable activities must be at least 5.
  • Non-continuous evaluation:
    In order to pass the course, at least 40% of the grade must be obtained in each of the two evaluable activities of the modality, laboratory practicals and final exam.
    The weighted grade of the evaluable activities must be at least 5.

Specifications for the resit/retake exam:
In order to pass the course, students must obtain at least 40% of the grade in each of the two evaluable activities of the modality, laboratory practicals and final exam.
The weighted grade of the evaluable activities must be at least 5.
Specifications for the second resit / retake exam:
In order to pass the course, students must obtain at least 40% of the grade in each of the two evaluable activities of the modality, laboratory practicals and final exam.
The weighted grade of the evaluable activities must be at least 5.
9. Assignments, course calendar and important dates
Not related to the syllabus/contents
Hours hours
Class Attendance (practical) [PRESENCIAL][Practical or hands-on activities] 31
Study and Exam Preparation [AUTÓNOMA][Self-study] 70
Other off-site activity [AUTÓNOMA][Problem solving and exercises] 20
Progress test [PRESENCIAL][Combination of methods] 2
Final test [PRESENCIAL][Combination of methods] 2

Unit 1 (de 4): AMINO ACIDS, PEPTIDES AND PROTEINS: Classification. Stereochemistry. Acid-base behavior. Isoelectric point. Analysis of amino acids. Synthesis methods. Enantioselective synthesis. Peptides. Determination of peptide structure: amino acid analysis. Sequence analysis. Analysis of terminal groups: N-terminal and C-terminal. Selective hydrolysis of peptides. Peptide synthesis strategy. Protection of the amino group. Protection of the carboxyl group. Activation and coupling. Peptide bonds formation. Peptides synthesis in solid phase. Merrifield method. Secondary structure of peptides and proteins. Tertiary structure. Coenzymes. Quaternary structure of proteins. Hemoglobin.
Activities Hours
Class Attendance (theory) [PRESENCIAL][Lectures] 5
Workshops or seminars [PRESENCIAL][Problem solving and exercises] 2

Unit 2 (de 4): CARBOHYDRATES AND NUCLEIC ACIDS: Introduction. Classification. Fischer projections. D-L notation system. Aldoses and ketoses. Rosanoff classification. Cyclic forms: Furanoses, pyranoses. Mutarotation. Anomeric effect. Glycosides. Disaccharides. Polysaccharides. Cell surface glycoproteins. Reactivity of monosaccharides. Reaction with phenylhydrazine. Reduction. Oxidation. Reactions of epimerization, isomerization and retroaldol degradation. Reaction with acid. Formation of thioacetals. Reaction with carbonyl compounds. Chain extension. Aldose degradation reactions. Nucleic acids: nucleosides, nucleotides, nucleic acids.
Activities Hours
Class Attendance (theory) [PRESENCIAL][Lectures] 6
Workshops or seminars [PRESENCIAL][Problem solving and exercises] 2
Group tutoring sessions [PRESENCIAL][Combination of methods] 1

Unit 3 (de 4): METABOLITES DERIVED FROM ACETATE: Acetylcoenzyme A. Fatty acids, fats and waxes. Biosynthesis of fatty acids. Phospholipids. Prostaglandins. Thromboxanes. Leukotrienes. Terpenes. Isoprene rule and classification of terpenes. Biosynthesis of terpenes. Mevalonic acid route. Linear, monocyclic and bicyclic terpenes. Steroids: structure. Biosynthesis of cholesterol. Carotenoids: structure. Chemistry of vision.
Activities Hours
Class Attendance (theory) [PRESENCIAL][Lectures] 3
Workshops or seminars [PRESENCIAL][Problem solving and exercises] 2

Unit 4 (de 4): OTHER SECONDARY METABOLITES: Polyphenols. Shikimic acid route. Galotanines. Hydroxycinnamic acids. Coumarins. Polyketides route. Naphthoquinones. Anthraquinones. Tetracyclines. Flavonoids. Isoflavonoids. Alkaloids. Alkaloids derived from ornithine and lysine. Alkaloids with pyrrolidine and piperidine structure. Alkaloids with pyrrolizidine and quinolizidine structure. Alkaloids with pyridine structure. Alkaloids derived from phenylalanine and tyrosine. Alkaloids derived from tryptophan: indole alkaloids. Alkaloids derived from purines.
Activities Hours
Class Attendance (theory) [PRESENCIAL][Lectures] 2
Workshops or seminars [PRESENCIAL][Problem solving and exercises] 2

Global activity
Activities hours
10. Bibliography and Sources
Author(s) Title Book/Journal Citv Publishing house ISBN Year Description Link Catálogo biblioteca
Carey, F. A. Química Orgánica, 6ª Ed. McGraw-Hill 970-10-5610-8 2006 It can be found in the UCLM General Library Ficha de la biblioteca
Claramunt Vallespí, R,; Farrán Morales, Á.; López García, C.; Pérez Torralba, M.; Santa María Gutierrez, D. Química Bioorgánica y Productos Naturales UNED Editorial 978-84-362-6624-5 2013 It can be found in the UCLM General Library Ficha de la biblioteca
García Calvo-Flores, F.; Dobado, J. A. Problemas resueltos en Química Orgánica, 1ª Ed. Thomson 978-84-9732-458-8 2008 It can be found in the UCLM General Library  
Gil Ruiz, P. Productos Naturales, 1ª Ed. Univ. Pública de Navarra 84-95075-91-1 2002 It can be found in the UCLM General Library Ficha de la biblioteca
Herbert, R. B. The Biosynthesis of Secondary Metabolites Chapman and Hall 0-412-27720-4 1989 It can be found in the UCLM General Library Ficha de la biblioteca
Levy, D. E.; Fügedi, P. The Organic Chemistry of Sugars, 1ª Ed. CRC Press 978-0824753559 2005  
Mann, J. Secondary Metabolism Oxford Chemistry Series 0-19-855529-6 1987 It can be found in the UCLM General Library Ficha de la biblioteca
Mann, J.; Davidson, S.; Hobbs, J.; Banthorpe, D.; Harborne, J. Natural Products Prentice Hall 978-0582060098 1994  
Marco, J. A. Química de los Productos Naturales, 1ª Ed. Sintesis 84-9756-403-0 2006 It can be found in the UCLM General Library Ficha de la biblioteca
McMurry, J. Organic Chemistry: with Biological Applications, 2ª Ed. Brooks/Cole 9780495391449 2011 It can be found in the UCLM General Library Ficha de la biblioteca
McMurry, J.; Begley, T. P. The Organic Chemistry of Biological Pathways, 1ª Ed. Robert & Company Publishers 0-9747077-1-6 2005 It can be found in the UCLM General Library Ficha de la biblioteca
Meislich, H.; Meislich, E. K.; Sharefkin, J. 3000 Solved Problems in Organic Chemistry, 1ª Ed. McGraw Hill 0-07-056424-8 1994 It can be found in the UCLM General Library Ficha de la biblioteca
Vollhardt, K. P. C.; Schore, N. E. Química Orgánica: Estructura y Función, 5ª Ed. Omega 978-84-282-1431-5 2007 It can be found in the UCLM General Library Ficha de la biblioteca
Wade, L. G. Jr. Química Orgánica, 5ª Ed. Pearson Educación 0-13-110310-5 2004 It can be found in the UCLM General Library Ficha de la biblioteca



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