ADVANCED ORGANIC SYNTHESIS LABORATORY

This course spans multiple degree programs and aims to enhance knowledge and skills in organic chemistry through intensive hands-on laboratory work. For Chemistry majors, it offers a highly innovative opportunity to learn concepts such as sustainability, chirality, molecular characterization, chemical reactivity, selectivity, and retrosynthesis through a unique, intensive, and highly effective approach based on teamwork and problem-solving. It is also particularly well-suited for students in other scientific degree programs where chemistry—and organic chemistry in particular—is a foundational subject.

The expected learning outcomes can be subdivided into the following specific areas:

1. Knowledge and understanding
i) Knowing laboratory instrumentation, its assembly, and its functions;
ii) Knowing how to monitor the progress of reactions using TLC and NMR techniques;
iii) Knowing techniques for the isolation and purification of organic products, such as distillation, crystallization, and chromatography.

2. Applying knowledge and understanding
i) Understanding and having learned the basics of the instrumental techniques available in the laboratory, such as electron ionization mass spectrometry (GC-MS), IR, and NMR;
ii) Knowing how to correlate information obtained from different analytical techniques (for example: identification of functional groups via IR, fragment analysis via mass spectrometry, assignment of isomers via NMR);
iii) Relating the spectroscopic properties of molecules to their chemical nature (for example: acidity of hydrogen atoms and chemical shift in NMR, presence of IR absorptions and molecular symmetry).

3. Making judgements
i) The ability to identify, based on collected information, the chemical course of a reaction and to determine its isolated yield and product purity.

4. Communication skills
i) Knowing how to communicate constructively with the instructor while maintaining a high level of attention and chemical understanding, using correct terminology and nomenclature in a concise manner and with appropriate confidence in presentation.
ii) Knowing how to maintain a laboratory notebook that ensures the reproducibility of the operations performed.

5. Learning skills
i) Knowing how to integrate the information provided by the instructors through constructive dialogue with other students of various levels of preparation.
ii) Having problem-solving and teamwork skills to solve synthetic and structural problems in organic chemistry.

To fully understand and appreciate this course, students should have already met the learning objectives of the core Organic Chemistry courses, as familiarity with the reactivity of functional groups is required. Additionally, a minimum passing grade in the Organic Chemistry course is required, in accordance with the guidelines set out in the annual call for applications for the course

The course, structured as an organic synthesis laboratory challenge, covers the multi-step synthesis of complex molecules, focusing on the installation of appropriate functional groups, stereochemistry, and molecular symmetry. The specific nature of the reactions changes from year to year, as students must not know them in advance to allow for direct, hands-on learning while performing the experiments. The integration of manual laboratory skills with knowledge of organic chemistry reactivity and structural characterization is fundamental.

As an example, the multi-step synthesis from the previous edition is presented below:
D-mannitol → di-O-isopropylidene-D-mannitol → (E)-1,2-bis((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethene

Spectroscopic Methods in Organic Chemistry
Manfred Hasse, Herbert Meier, Bernd Zeeh, E. Rossi

Spectrometric Identification of Organic Compounds
Robert M. Silverstein, Francis X. Webster, David J. Kiemle

The student will record the results of the experiments, the characterizations, and the answers to the questions in the laboratory notebook. The material present in the laboratory notebook will be evaluated by the instructors for the definition of the standings of the challenge and for the final assignement of the grade

written

The instructor is responsible for ensuring the authenticity and originality of all examinations and coursework. In cases of suspected academic misconduct, an additional on-site assessment may be required during the exams, which may differ from the standard format.

Grade 18-22 basic knowledge of the content of the course, sufficient ability to connect the topics discussed, sufficient laboratory activities and reports.
Grade 23-26 fair knowledge of the content of the course, good ability to connect the topics discussed, good laboratory activities with detailed and correct reports.
Grade 27-28 very good knowledge of the content of the course, excellent ability to connect the topics discussed, excellent laboratory activities with detailed and error-free reports.
Grade 29-30 excellent knowledge of the content of the course, excellent ability to connect the topics discussed, excellent laboratory activities and reports.
Grade 30 cum laude as for grade 29-30 plus deep understanding of stereochemical features of the lab activities performed and how this affects characterization spectra

The course is delivered through a series of short videos to be watched prior to the laboratory session as preparation. This is followed by three full days of experimental activities—covering organic synthesis, purification, and characterization—conducted in the teaching laboratory

The teacher is available for discussion with the students on the topics of the course, Please, get in contact by email: alesca@unive.it
Accessibility, Disability and Inclusion
Accommodation and support services for students with disabilities and students with specific learning impairments:
Ca’ Foscari abides by Italian Law (Law 17/1999; Law 170/2010) regarding support
services and accommodation available to students with disabilities. This includes students with mobility, visual, hearing and other disabilities (Law
17/1999), and specific learning impairments (Law 170/2010). In the case of disability or impairment that requires accommodations (i.e., alternate
testing, readers, note takers or interpreters) please contact the Disability and Accessibility Offices in Student Services: disabilita@unive.it

This subject deals with topics related to the macro-area "Natural capital and environmental quality" and contributes to the achievement of one or more goals of U. N. Agenda for Sustainable Development