COURSE OBJECTIVE:
Introducing students to the basic principles of simple and more accessible synthesis in the laboratory and industry. Synthesis planning and retrosynthesis of target organic molecules. Critical thinking when choosing the most suitable synthetic routes for conducting organic syntheses in the laboratory.
COURSE IMPLEMENTATION PROGRAM:
WEEK 1
Introduction. Organic synthesis planning: synthetic plan, strategy and control. Retrosynthesis.
WEEK 2
Chemoselectivity. Regioselectivity: controlled aldol reactions.
WEEK 3
Stereoselectivity: stereoselective aldol reactions. An alternative strategy for enone synthesis.
WEEK 4
Creating a new C-C bond that leads to an increase in molecular structure. Ortho-strategy for aromatic compounds. Controlled Michael additions.
WEEK 5
Specific enol equivalents. Enolati. Allyl anions. Homoenolates. Acyl-anion equivalents.
WEEK 6
C-C double bond. Synthesis of double bonds of defined stereochemistry.
WEEK 7
Vinyl anionic equivalents. Electrophilic attack on alkenes.
WEEK 8
Vinyl cations. Palladium catalyzed reactions. Allyl alcohols.
WEEK 9
Stereochemistry. Stereochemistry control and relative stereochemistry control. Resolution
WEEK 10
Asymmetric synthesis with natural products as starting reactants. Asymmetric catalysis: formation of C-O and C-N bonds.
WEEK 11
Asymmetric catalysis: formation of C-H and C-C bonds. Asymmetric substrate-based strategy.
WEEK 12
Enzymes: biological methods in asymmetric synthesis. Asymmetric synthesis strategy.
WEEK 13
Functional group strategy. Pyridine functionalization. Oxidation of aromatic compounds.
WEEK 14
Functionalization of pericyclic reactions: synthesis of nitrogen heterocycles by cycloadditions and sigmatropic rearrangements
WEEK 15
Synthesis and chemistry of azoles and other heterocycles with two or more heteroatoms.
DEVELOPING GENERAL AND SPECIFIC COMPETENCIES OF STUDENTS
Planning the synthesis and retrosynthesis of target organic molecules, critical thinking when selecting the most suitable synthetic pathways for conducting organic synthesis in the laboratory.
STUDENT'S OBLIGATIONS:
Students are required to attend lectures.
Students are required to do all the lab exercises.
Students are required to submit a Work Assignment.
Students are required to access knowledge tests and colloquia (related to laboratory exercises).
CONDITIOND FOR OBTAINING SIGNATURES:
80% attendance at lectures.
Completed laboratory exercises, prepared and submitted papers, passed colloquium in laboratory
exercises.
Committed Work Task.
TEACHING METHODS:
Lectures (ex cathedra).
Laboratory exercises (practical work in groups under the supervision of an assistant).
Consultations by arrangement with students.
MANNER OF EXAMINATION OF KNOWLEDGE AND EXAMINATION:
Laboratory exercises colloquia.
2 compulsory partial exam during the semester (60% of points on each of the tests bring exemption from the oral exam).
Work assignment.
Written exam (requires 55% points to pass).
Oral exam.
METHOD OF MONITORING THE QUALITY AND PERFORMANCE OF COURSES:
Student survey
METHODOLOGICAL PREREQUISITES:
Passed exams from the course of the 1st academic year and the courses Organic Chemistry I and Organic Chemistry II.
COURSE LEARNING OUTCOMES:
1. Define and recognize the most important principles and principles of simple and multistage organic synthesis.
2. Understand and analyze retrosynthetic analysis of target organic molecules.
3. Plan and identify possible synthetic pathways for the synthesis of target molecules.
4. Integrate the acquired knowledge to identify and select the most suitable synthetic pathway for the synthesis of the target molecule with respect to the available starting chemicals.
5. Think critically and identify possible problems when selecting a particular synthetic route given the existing laboratory conditions for the synthesis of target molecules.
6. Synthesize selected target molecules.
LEARNING OUTCOMES AT PROGRAM LEVEL:
1. Interpret chemical information and data.
2. Present study-related materials (orally and in writing) to a professional audience.
3. Search for information available on the Internet.
4. Apply standard laboratory procedures and instrumentation for preparative or analytical purposes, for organic and inorganic systems.
5. Demonstrate the ability to engage in interdisciplinary teamwork.
6. Assess the risks associated with the use of certain chemicals or laboratory procedures.
TEACHING UNITS WITH ASSOCIATED LEARNING OUTCOMES AND EVALUATION CRITERIA
1. Organic synthesis planning: synthetic plan, strategy and retrosynthesis
Learning outcomes
- define the basic principles and importance of organic synthesis planning
- recognize the concepts of synthetic plan and strategy of organic synthesis
- define and interpret the concept of retrosynthesis
- abolish the concept of synthons and their importance in planning organic synthesis
Evaluation criteria
- understand the importance of planning organic synthesis in the synthesis of new target molecules
- apply and present the strategy and synthetic plan in planning the synthesis of the target molecule
- apply retrosynthesis in planning the synthesis of the target molecule
- use adequate synthons when proposing synthetic pathways of the target molecule
2. Chemoselectivity; regioselectivity; stereoselectivity
Learning outcomes
- recognize chemoselectivity and its role in planning organic synthesis
- recognize regioselectivity and its role in planning organic synthesis
- recognize stereoselectivity and its role in planning organic synthesis
- present and interpret the individual role of these selectivities in the synthesis of target molecules
Evaluation criteria
- understand the concepts of chemoselectivity, regioselectivity and stereoselectivity
- notice the difference between the stated selectivities
- understand the role of these selectivities and their application in the synthesis of target molecules
- apply the stated selectivities in the synthesis of target molecules
3. Creation of new C-C and C = C bonds leading to increased molecular structure
Learning outcomes
- analyze the basic ways of synthesis of C-C bonds
- analyze the basic ways of synthesis of C = C bonds
- identify the most suitable synthetic pathways with respect to the desired increase in molecular structure
- recognize the difference between individual synthetic methods on the example of the synthesis of some target molecules
Evaluation criteria
- know the usual ways of synthesis of C-C bonds
- know the usual ways of synthesis of C = C bonds
- be able to critically choose the most suitable way of synthesis of C-C bonds or C = C bonds with regard to the desired increase in molecular structure
- apply the mentioned synthetic methods in the synthesis of target molecules
4. Asymmetric synthesis and catalysis in the formation of C-C, C-H, C-N and C-O bonds
Learning outcomes
- analyze the concept of asymmetric synthesis and asymmetric catalysis
- recognize the ways of asymmetric synthesis of C-C and C-H bonds
- identify ways of asymmetric synthesis of C-N and C-O bonds (C-heteroatom bonds)
- present and interpret the most suitable synthetic pathways for the formation of appropriate connections
Evaluation criteria
- understand asymmetric synthesis and catalysis and their application in organic synthesis planning
- know the ways of asymmetric synthesis of C-C and C-H bonds
- know the ways of asymmetric synthesis of C-N and C-O bonds
- apply the mentioned methods of asymmetric synthesis in planning the synthesis of target molecules
5. Functional group strategy, synthesis of azoles and heterocycles with two or more heteroatoms
Learning outcomes
- interpret the most important functional groups for planning organic synthesis
- recognize the role of functional groups in organic synthesis
- analyze the methods of synthesis of azoles and nitrogen heterocycles
- analyze the methods of synthesis of heterocycles with two or more heteroatoms
Evaluation criteria
- know the most important functional groups, especially for the synthesis of heterocycles
- understand the ways of synthesis of azoles and nitrogen heterocycles
- understand the ways of synthesis of heterocycles with two or more heteroatoms
- apply the mentioned methods of heterocycle synthesis in planning the synthesis of target molecules
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P. Wyatt, S. Warren, ORGANIC SYNTHESIS: STRATEGY AND CONTROL, John Willey and Sons, New York, 2007.
T. W. G. Solomons, ORGANIC CHEMISTRY, 8th Ed, John Willey and Sons, New York, 2004.,
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F. Serratosa, J. Xicart, ORGANIC CHEMISTRY IN ACTION, 2nd Ed, Elsevier, Amsterdam, 1996.
S. H. Pine, ORGANSKA KEMIJA (prijevod I. Bregovec, V. Rapić), Školska knjiga, Zagreb, 1994.,
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