COURSE: ORGANIC CHEMISTRY-II

SUBJECT: Organic Chemistry

MODULE: Chemistry
STUDIES: Degree in Chemsitry

Page 1 of 7

GENERAL FEATURES*
Type: ☐ Basic Training, ☑ Mandatory, ☐ Elective
☐ Final degree project, ☐ External practices
Duration: Semestral Semester/s: 7 and 8
Number of ECTS credits: 6
Languages/s: Spanish, Catalan, English

DESCRIPTION

BRIEF DESCRIPTION AND JUSTIFICATION (the meaning of the subject in relation to the
studies. Between 100 and 200 words.)

The subject of Organic Chemistry-II is designed to broaden and deepen the student's
knowledge in organic chemistry particularly based on six areas: Stereochemistry, Physical
Chemistry Organic, Organometallic Chemistry (Block I), Organic Synthesis (Block II), Current
Reactions and Synthetic Methodology and Heterocyclic Chemistry (Block III). This aims to
train students with a multidisciplinary base for applications ranging from materials science,
through biochemistry and natural products to the pharmaceutical medicinal chemistry

COMPETENCIES (of the subject according to the competencies pre-assigned in the

subject.)

 Be able to understand and apply knowledge of organic chemistry (structure, reactivity,

stereochemistry, ...) in the practice of Chemical and Biomolecular Sciences (E2.1,
MECES-1)
 Be able to identify, formulate and solve typical problems of Organic Chemistry (reaction
mechanisms, prediction of reaction products, synthetic problems, etc.) (E7.2, MECES-
2)
 Be able to design and planning synthetic routes for organic molecules in accordance
with the requirements established for them (E5, E8.1, E10)
 Be able to assess the impact of organic chemistry in sustainable development of
society (T5)

PREREQUISITES* (modules, subjects, courses or knowledge needed to monitor the course.

It can be noted courses which must have been completed.)

The competencies of the subjects of:

Organic Chemistry, Inorganic Chemistry, Physics, Biochemistry.

PREREQUISITES: The prerequisite courses taught, especially those acquired in Organic

Chemistry.

* These features should not be modified without the approval of organs responsible for the
high-level academic structures (subject, module and/or study plan).
 COURSE: ORGANIC CHEMISTRY-II
SUBJECT: Organic Chemistry
MODULE: Chemistry
STUDIES: Degree in Chemsitry

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CONTENTS (according to sections which constitute the list of contents of the course to the
second level detail.)

Part I: Structure and Reactivity

1. Structure of Organic Molecules

1.1. Atoms and molecules. Bonds and angles. Hybridization

1.2. Constitution, configuration and conformation
1.3. Isomerism. Historical background. Optical properties. Biological importance of
enantiomeric. Diastereomers
1.4. Preparation of homochiral substances. Resolution. Analysis of enantiomeric mixtures.
Racemization
1.5. Reactivity and stereoisomerism. Topicity and prochirality
1.6. Asymmetric synthesis. Stereoselectivity and is stereospecificity. Chiral pool. Chiral
Induction. Asymmetric catalysis
1.7. Conformers. Baeyer’s Theory. Atropoisomers

2. Reactivity in Organic Chemistry

2.1 Reacciones Polares.

2.1.1 Electróphiles and nucleophiles. Umpolung.
2.1.2 Organometallic chemistry
2.1.2.1 Organometallic Compounds
2.1.2.2 Organometallic bonding. 18-electron rule
2.1.2.3 Reactivity of the organometallic compounds

2.2 Pericyclic reactions

2.2.1 Pericyclic reactions. Woodward-Hofman rules
2.2.2 Cycloadditions: Diels-Alder and 2+2
2.2.3 Sigmatropic rearrangements

2.3 Radical reactions

2.3.1 Radical mecanisms
2.3.2 Radical reactions with tin compounds

Part II: Síntesis de moléculas orgánicas

3. Organic Synthesis

3.1 Organic Synthesis: Art and Science

3.2 Selectivity in synthesis. Protecting groups
3.3 Disconnections of carbonyl compounds

* These features should not be modified without the approval of organs responsible for the
high-level academic structures (subject, module and/or study plan).
 COURSE: ORGANIC CHEMISTRY-II
SUBJECT: Organic Chemistry
MODULE: Chemistry
STUDIES: Degree in Chemsitry

Page 3 of 7

3.4 Functional group transformations: C-Het bond formation

3.4.1 Steglish reaction
3.4.2 Mitsunobu reaction
3.4.3 Lawesson reagent
3.5 Functional group transformations: Redox Reactions
3.5.1 Oxidations with S compounds
3.5.2 Reductions with B and Al compounds. CBS Reduction
3.5.3 Hydrogenation with Rh complexes

Part III: Synthetic Transformations

4. C-C bond formation: alkylation and acylation

4.1 Enamines
4.2 Mannich reaction
4.3 Silyl enol ethers. Mukayama reaction
4.4 Vilsmeier-Haack acylation
4.5 Additions of organomagnesium, organolithium. 1,3-dithianes
4.6 Gilman reagents. Conjugated additions
4.7 Neguishi, Kumada, Suzuki, Stille reactions

5. Formation of olefins and alkynes

5.1 Reacción de Wittig Wittig reaction

5.2 Julia and Peterson reactions
5.3 Heck reaction
5.4 Metathesis reactions: RCM, ROMP, ADMET
5.5 McMurry reaction
5.6 Corey-Fuchs reaction
5.7 Sonogashira reaction

6. Química Heterocíclica

6.1. Synthetic strategies. Intramolecular and intermolecular constructions

6.2. 3-membered heterocycles
6.3. 4-membered heterocycles
6.4. 5-membered heterocycles
6.5. 6-membered heterocycles

* These features should not be modified without the approval of organs responsible for the
high-level academic structures (subject, module and/or study plan).
 COURSE: ORGANIC CHEMISTRY-II
SUBJECT: Organic Chemistry
MODULE: Chemistry
STUDIES: Degree in Chemsitry

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METODOLOGY

TRAINING ACTIVITIES * (complete the table relating activities and workload to ECTS
credits and competencies.)

Training activities ECTS Competencies

Credits
Concept Sessions 1.1
E2.1, E7. 2, E10, T5
Sessions solving exercises, problems and cases 0.18 E2.1, E7.2
Practical / laboratory work 1.1 E5, E8.1, E10, E11,
T5
Personal study activities of students 2, 4 E2.1, E7.2, E10 T5

Evaluation activities (tests, monitoring controls ...) 0, 18 E2.1, E7.2, E10

TOTAL 5

EXPLANATION OF THE METHODOLOGY (justifying the teaching methods used related to

competencies and course contents. Between 100 and 200 words)

Theoretical Sessions: concepts exposition based on presentations or explanations (possibly

including demonstrations) by the teacher.

Sessions for solving exercises, problems and cases: Resolution of exercises, approach /
problem solving and presentation / discussion of cases by the teacher with the active
participation of students.

Practical work / laboratory: Period of laboratory activities or similar (computer practice,

projects, workshops, etc…) by the student under the direct supervision of the teacher.

Personal study activities: student personal work is required to acquire the skills of each
subject and assimilate the knowledge outlined in the theoretical sessions and in the solving
exercises sessions, using when necessary the recommended support.

Evaluation activities (exams, monitoring controls) oral and/or written tests made during the
course or after it.

* These features should not be modified without the approval of organs responsible for the
high-level academic structures (subject, module and/or study plan).
 COURSE: ORGANIC CHEMISTRY-II
SUBJECT: Organic Chemistry
MODULE: Chemistry
STUDIES: Degree in Chemsitry

Page 5 of 7

EVALUATION

METHODS OF EVALUATION * (Complete the table relating assessment methods,

competencies and the weight in the rating of the course)

Methods of evaluation % Competencies

Final exam 40 E2.1, E7.2, E10
Follow-up activities 20 E2.1, E7.2
Homework and presentations 10 E2.1, E10, T5
Experimental work or fieldwork 25 E5, E8.1
Participation 5 E8.1, T5

LEARNING OUTCOMES (Explanation of the achievements of students that allow

competency assessment, relating to competencies and assessment methods.)

1. Demonstrate understanding and ability to apply knowledge of organic chemistry

(structure, reactivity, stereochemistry, ...) in the practice of Chemical and Biomolecular
Sciences (E2.1, MECES-1)
2. Identify, formulate and solve problems typical of Organic Chemistry (reaction
mechanisms, prediction of reaction products, synthetic problems, etc.) ( (E7.2,
MECES-2)
3. Designing and planning synthetic routes to organic molecules according to the
requirements for them (E10, E5, E8.1)
4. Assess the impact of organic chemistry in sustainable development of society (T5)

EVALUATION (Explanation of the evaluation method of the subject.)

Experimental work Note Experimental Laboratory (L)

Papers and presentations Average rating of a bibliographic work
presentation and the preparation of
synthetic route map (T)

* These features should not be modified without the approval of organs responsible for the
high-level academic structures (subject, module and/or study plan).
 COURSE: ORGANIC CHEMISTRY-II
SUBJECT: Organic Chemistry
MODULE: Chemistry
STUDIES: Degree in Chemsitry

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Exams and follow-up activities

Follow-up control I Exam during class time (CI)

Follow-up control II Exam during class time (CII)
Examination Final exam (F)

The final rating is the best among:

(L + 0.25 • 0.10 • 0.10 • T + CI + CII + 0.4 0.10 • • F) + Participation (0-0, 0 5) (all marks must
be higher than 4) and (F).

EVALUACION OF THE COMPETENCIES (Define calculation expressions for each

competency in terms of the corresponding evaluation activities)

For the evaluation of the E2.1 competency will be used the mark of the reviews as indicator.
For the evaluation of competency E5, is used the mark of the experimental work as indicator.
For the evaluation of the competency E7.2 will be used the mark of the reviews as indicator.
For evaluation of the competency E8.1 will be used the mark of the experimental work as
indicator. For the assessment of competency E10 will be used the mark of the reviews as
indicator. For the assessment of competency T5 will be used the mark of the reviews and
participation as indicator.

BIBLIOGRAPHY (recommended and student accessible.)

BASIC BIBLIOGRAPHY:
 M.B. Smith, J. March, March’s Advanced Organic Chemistry. Reactions,
Mechanisms, and Structure, John Wiley & Sons, 5th ed., New York, 2001. ISBN:
0471585890
 E.L. Eliel, S.H. Wilen, M.P. Doyle, Basic Organic Stereochemistry, Wiley-
Interscience, John Wiley & Sons, New York, 2001. ISBN: 047137499
 Ch. Elschenbroich, A. Salzer, Organometallics. Wiley-VCH, 1989.ISBN: 0895738686
 J.A. Joule, K. Mills, Heterocyclic Chemistry, 4th Ed., Blackwell Science Inc., 2000,
ISBN: 0632054530
 W. Reusch (whreusch@pilot.msu.edu), Virtual Textbook of Organic Chemistry,
http://www.cem.msu.edu/~reusch/VirtualText/intro1.htm, (22-01-2013).
 J. Clayden, N. Greeves, S. Warren, Organic Chemistry (2nd edition), Oxford University
Press, Oxford, 2012.

* These features should not be modified without the approval of organs responsible for the
high-level academic structures (subject, module and/or study plan).
 COURSE: ORGANIC CHEMISTRY-II
SUBJECT: Organic Chemistry
MODULE: Chemistry
STUDIES: Degree in Chemsitry

Page 7 of 7

BIBLIOGRAPHY or SUPPLEMENTARY MATERIAL

 R.K. Mackie, D.M. Smith, R.A. Aitken, Guidebook to Organic Synthesis, 3rd. Ed.,
Pearson PTP, 2000. ISBN: 0582290937
 J. McMurry, Organic Chemistry (5th edition), Brooks/Cole Publishing Company,
Pacific Grove, California, 2000. ISBN: 0534373674
 A.R. Katritzky, A.F. Pozharskii, Handbook of Heterocyclic Chemistry, Pergamon
Press; 2nd edition, 2000, ISBN: 0080429890
 S. Seyhan. Química Orgánica. Tomos 1 y 2. Ed. Reverté, 1997.
 R. T. Morrison, R. N. Boyd, Organic Chemistry (6th edition), Prentice Hall International
Inc, New Jersey, 1992
 E. Fernández, F. Fariña, Nomenclatura de la Química Orgánica (Secciones A, B, C,
D, E, F y H), CSIC-RSEQ, Madrid, 1987
 J. I. Borrell, J. Teixidó, J. L. Falcó, Síntesis Orgánica, Ed. Síntesis, Madrid, 1999.
 G. Procter, Asymmetric Synthesis, Oxford University Press, Oxford 1996.
 M. B. Smith. Organic Synthesis, 2nd Ed., Mc Graw-Hill, New York, 2001.
 G.O. Spessard, G.L. Miessler, Organometallic Chemistry, Prentice Hall, 1996.
 F. Diederich and P.J. Stang (Editors), Metal-catalysed Cross-coupling Reactions,
Wiley-VCH, 1998.
 D. Sanchez-García, J. Teixidó, J.I. Borrell, L. Ros, Metales de Transición en Síntesis
Orgánica, Ed. Síntesis, Madrid, 2013.

DOCUMENT RECORD
PREVIOUS CHANGES (Indicate date/s, the most recent first)
26 de July de 2011, Dr. David Sánchez García

LAST REVISION (Indicate date/s and author/s.)

6 de May de 2015, Dr. David Sánchez García

* These features should not be modified without the approval of organs responsible for the
high-level academic structures (subject, module and/or study plan).