Ateneo - UPO

Module Advanced Organic Chemistry
The course covers stereoselective syntheses, the use of chiral pool, chiral auxiliaries other than chiral catalysts (organic or metal complexes) for asymmetric synthesis.
Then, various types of pericyclic and cycloaddition reactions, including click reactions will be examined. Aromatic and saturated heterocyclic chemistry, radicalic and rearrangement reactions will be also considered. Finally, non-conventional synthetic approaches such as sonochemistry, mechanochemistry, microwave and flow chemistry will be analyzed.
Module Laboratory
The laboratory course aims to provide the student with an advanced picture of synthetic organic chemistry as well as adequate skills to tackle more complex problems.

Module Advanced Organic Chemistry
J. Clayden, N. Greeves, S. Warren, Organic Chemistry , 2nd Edition, Oxford University Press 2012 (ISBN 978-0-19-927029-3). F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part B: Reaction and Synthesis, Springer (ISBN 978-0-387-71481-3).
Slides and other material given by the teacher.
Module laboratory
Carey, Sundberg, "Advanced Organic Chemistry: Reactions and Synthesis” Springer. J. Leonard, B. Lygo, G. Procter «Advanced Practical Organic Chemistry», 3rd ed. (2013), Taylor & Francis-CRC.

Module Advanced Organic Chemistry
The course is designed to increase the organic chemistry knowledge by studying important class of organic reactions and synthetic strategies not explained on other organic chemistry courses. The students will obtain the principles of modern synthetic strategies: pericyclic reactions, asymmetric synthesis, heterocyclic chemistry using also non-conventional and greener approaches.

Module Laboratory
The course aims to provide the student with knowledge associated with asymmetric synthesis, with the design and synthesis evaluation of complex organic molecules.
The students will put into practice some of the modern organic reactions: pericyclic reactions, asymmetric synthesis and heterocyclic chemistry also using unconventional and "greener" synthesis methods.

Module Advanced Organic Chemistry
Contents of the Organic Chemistry courses of the Batchelor Degree.
Module laboratory
• Fundamentals of organic chemistry, stereochemistry and structure and reactivity of organic and organometallic compounds.
• Basic experimental techniques of the organic chemistry laboratory.
• Characterization of organic compounds by 1H NMR and 13C NMR.
• Fundamentals of chromatography.
• Ability to search chemical databases (eg SciFinder) for properties, methods of preparation and characterization of organic compounds.
• Experience in writing a scientific report.

Module Advanced Organic Chemistry
The course is based on classroom lectures and exercises. During the lessons, the literature references for various topics will be given to enable further investigation and encourage the student to read the primary literature.
The concepts of the course will be discussed in the classroom and applied directly during exercises in the classroom.
Module laboratory
The course includes a certain number of multistep synthesis (generally conducted in groups of two students) of polyfunctionalized organic molecules, their purification and characterization with 1H and 13C NMR spectroscopy and mass spectrometry. The teacher will provide a laboratory manual which shows the outline of the experimental work to be performed for that specific reaction.

Module Advance Organic Chemistry
The teacher is available to the student for any clarification or explanation of the topics covered during the course.
Ongoing learning will be assessed through classroom exercises and collegial discussions.
Module laboratory
The learning is checked at the beginning of each laboratory session: a student is called to the blackboard and asked to explain in detail the reaction of the previous day, highlighting the key steps, the mechanism and the results obtained. The discussion is collective: the other students are required to participate to the discussion.

Module Advanced Organic Chemistry
The exam consists of a presentation of a research carried out by the student on a particular chosen subject specifying also the experimental part, followed by an oral examination consisting of 2-3 questions on the entire program of the course. The evaluation will take place based on the efficacy of the presentation and by testing the level of the learning objectives previously described. The passing grade is achieved by demonstrating that the student has understood the subject and is able to use the basic concepts of the topics covered during the course through the exercises. The ability to correctly write formulas and reaction mechanisms in the written exam and on the blackboard is also essential in order to pass the exam.
Module laboratory
At the end of the course, the students shall bring the lab notebook to the teacher, correctly compiled for every experience carried out. The final report of each working group is sent to the teacher for evaluation at least two weeks before the oral exam of the first member of the group interested in taking the test.
The examination will feature at least three open questions concerning the reactions performed in the lab, as to evaluate the students' communication skills, and both her/his theoretical and practical knowledge.
The final grade will be formulated in a collegial way starting from the weighted average of the grades of the theoretical and laboratory course, considering the ability of the student to have assimilated the concepts of the two modules and to be able to apply the theoretical knowledge acquired.

Module Advanced Organic Chemistry
Pro-chiral centres and stereoselectivity in additions to alkenes and carbonyls: Felkin-Ahn model and chelate effect. Chiral pool and chiral auxiliary; enantiomeric excess. Asymmetric catalysis in hydrogenation, epoxidation and dihydroxylation reactions. CBS reagent and BINAP. Asymmetric synthesis of C-C bonds. Asymmetric aldolic reactions. Enzymes as catalysts. Stereoselectivity in cyclic molecules.
Pericyclic reactions: 1,3-dipolar cycloadditions; click chemistry; sigmatropic rearrangements, electrocyclic reactions.
Heterocyclic compounds and their derivatives (main heterocyclic compounds with one and with two heteroatoms, pyrrole, furan, thiophene, diazoles, pyridine, diazines, triazines, indole). Functionalization of pyridines; synthesis of aza-heterocycles via cycloaddition and sigmatropic rearrangements; synthesis and chemistry of azoles and other heterocycles with two or more heteroatoms.
Rearrangement reactions: vicinal group participation; Payne, pinacol, and Favorskii rearrangement: migration to heteroatoms: Baeyer-Villiger and Beckmann rearrangement; fragmentations and ring expansions; migrations to carbenes and nitrenes. Radicalic reactions: analysis of examples and applications.
Non-conventional synthetic approaches such as sonochemistry, mechanochemistry, microwave and flow chemistry. Examples of synthetic and industrial applications.
Module laboratory
The following reactions will be carried out in the laboratory, followed by the purification and characterization of the products:
1) Asymmetric aldol condensation
2) Determination of enantiomeric excess by derivatization with Mosher's acid (NMR)
3) Azide-alkyne click reaction
4) Bayer Villiger and Beckmann rearrangements from cyclododecanone
5) Synthesis of a bifunctional chelator (multistep synthesis)
6) Diels-Alder reaction followed by Curtius rearrangement.

Module Advanced Organic Chemistry
Objective 1: Knowledge and understanding.
Knowledge of the principles of stereoselective and stereospecific synthesis.
Knowledge of the frontier orbital theory and its use to explain reactivity, stereospecificity and regioselectivity of periciclic reactions.
Knowledge of the properties of heterocyclic systems.
Objective 2: Applying knowledge and understanding.
Ability to design a stereoselective and stereospecific synthesis.
Ability to explain specific reaction mechanisms.
Ability to apply the frontier orbital theory to explain reactivity, stereospecificity and regioselectivity of periciclic reactions.
Ability to compare the properties of heterocyclic systems and to propose synthesis and functionalization strategies.
Ability to carry out bibliographic and structural searches on organic molecules and reactions.
Ability to find a stereoselective synthesis for a chiral molecule.
Ability to explain the course and the stereochemistry of a reaction based on its mechanism.
Ability to discuss the possible reaction pathway according to the structure of the reagents and the reaction conditions.
Objective 3: Making judgements.
Ability to evaluate from the structure of a compound which predictions can be made about its molecular properties.
Ability to interpret and rationalize organic reactions in terms of reaction mechanism and to address the study of the subject through critical and non-mnemonic learning.
Objective 4: Communication skills.
Ability to prepare and give a presentation clear and functional on an advanced scientific paper or subject.
Ability to connect and compare different topics.
Ability to clearly organize and explain the answer by acquiring the appropriate terminology.
Objective 5: Learning skills
Ability to use teaching material for a critical and rational study.
Ability to update and expand knowledge of the discipline through the consultation of more advanced teaching texts and scientific publications on the subject.
Module laboratory
1. Knowledge and comprehension skills: the understanding of the basic reactions of synthetic organic chemistry is the main goal of this course. Moreover, both the theoretical, and the practical knowledge of how to operate in an organic lab, are required.
2. Ability to apply one's own comprehension and knowledge:
the student will have to demonstrate her/his knowledge of the basic reactions of synthetic organic chemistry, and in addition, to be able to apply the the acquired knowledge to lab operativity.
The student shall also be able to apply the above theoretical learnings to everyday laboratory practice. Hence, it is expected that he/she will be able to operate autonomously in the organic laboratory. Finally, the ability to fill in the lab notebook is requested.
3. Communication skills: the student will have to carry out the bibliographic search autonomously, demonstrating a correct exposition of the bibliographic search, demonstrating to possess an adequate scientific language.
4. Judgement ability: the pupil shall know how to discriminate among apparently equal synthetic pathways, thus showing a deep comprehension of the investigated reaction.
5. Learning abilities: they will be evaluated as the to face autonomously the study case (i.e., the bibliographic search).