Ateneo - UPO

The laboratory of Advanced Organic Chemistry aims to provide the student with an advanced picture of synthetic organic chemistry as well as adequate skills to tackle more complex problems.

J. Leonard, B. Lygo, G. Procter «Advanced Practical Organic Chemistry», 3rd ed. (2013), Taylor & Francis-CRC.
Alfonso et al. "Comprehensive Organic Chemistry Experiments for the Laboratory Classroom" (2016) Royal Society of Chemistry,
Carey, Sundberg, "Advanced Organic Chemistry: Reactions and Synthesis” Springer.

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.
The main skills to be acquired will be: predicting the properties and reactivity of organic compounds, knowing how to compare and evaluate different synthetic routes in order to know how to choose the most appropriate one, knowing how to safely perform laboratory operations for the preparation and purification of organic compounds , knowing how to interpret NMR and mass spectra, knowing how to draw up a concise and accurate report of the experiment performed.

• 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.

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. During the individual experiences, the teacher and the tutor will propose to the individual groups and collectively a comment and a discussion on the meaning of the operations carried out. The student will also have to draw up a laboratory notebook individually and write the laboratory reports commenting on both the theoretical and practical parts.

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.
Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/servicesstudents-physical-or-learning-disabilities
Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects.

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.
In addition, each of them has to perform a bibliographic search upon a historically significant reaction of organic chemistry.

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

How to fill in the laboratory notebook.
How to browse the on-line scientific literature, and how to carry out the study case (literature search).

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).