Learning objectives
At the end of the course the student is expected to:
- Know the principles of NMR and IR spectroscopy and of mass spectrometry; know the mechanisms of the reactions performed in the lab; understand the chemical processes that occur at every step of the experimental procedure; know the principles and the analysis procedures for the characterization of the organic compounds; know the appropriate methodologies to handle chemicals and chemical waste in safety conditions (knowledge and understanding);
- In the lab, prepare and purify an organic compound through simple methodologies working according to the safety guidelines; choose the appropriate method for the purification and analysis of a mixture; choose the appropriate chemical-physical methodology to ascertain the identity and the purity of the synthesized compounds and to obtain molecular properties; handle chemicals in safety conditions, including the correct waste disposal; correlate the structure, physical properties and reactivity of the main classes of organic compounds; collect scientific data through lab measurements, elaborate and interpret the collected data; predict the chemical shift and multiplicity of the 1H and 13C NMR signals of an organic compound; identify an organic molecule from spectroscopic data (applying knowledge and understanding);
- Collect and critically evaluate and present the experimental results obtained from activities in collaboration; design and perform an experiment; collect and evaluate literature data also from chemical database; handle chemicals in safety conditions, classify waste and dispose waste correctly; evaluate the environmental effects of chemical processes and evaluate the safety of workplaces (making judgements);
- Write a laboratory notebook; communicate with an appropriate chemical terminology both in written and oral form within professional activities; collaborate with other people also to apply appropriate safety procedures (communication skills);
- Work according to targets, in group or autonomously; adapt to work in different environments; interpret data from scientific literature, especially in applied fields (learning skills).
Prerequisites
Knowledge of the concepts explained in the General Chemistry and in the Organic Chemistry I and Organic Chemistry Lab I courses. Moreover, the student is required to attend the Organic Chemistry II course that take place in the same semester.
Course unit content
The course will provide the students the theoretical knowledge and the practical ability to perform an organic reaction in the lab and to determine the molecular structure of a simple compound from spectroscopic data.
Full programme
IR Spectroscopy: principles and investigation of different classes of organic molecules.
Mass Spectrometry: principles, main ionization techniques, main fragmentation mechanisms in electronic ionization MS.
1H and 13CNMR Spectroscopy: the spin concept, the vectorial model, continuous wave and FT-NMR, chemical and magnetic equivalence, chemical shift, spin-spin coupling, interpretation of the spectra of organic molecules.
Identification of unknown organic molecules from NMR, IR, and MS data.
Laboratory Experiences:
• Reduction of a ketone with sodium borohydride.
• Preparation of a Grignard reagent and synthesis of a tertiary alchol.
• Aldol condensation.
• Synthesis of a deuterated compound through Knoevenagel
condensation.
• Protection reaction of D-mannose with acetone.
• Lab exam consisting in an organic reaction to be performed autonomously.
Bibliography
Teaching materials:
the spectroscopy handouts will be available on the Elly platform before the beginning of the course. The workshop forms of the lab experiences will be uploaded on Elly as well and the students are requested to print them and bring them to class when indicated by the teacher.
Texts for consultation and further study:
Spectroscopy:
- M. Hesse, H. Meier, B. Zeeh, “Metodi spettroscopici in chimica Organica”, 2^ edizione, EdiSES, 2010.
- R. M. Silverstein, F. X. Webster, D. J. Kiemle, “Identificazione spettrometrica di composti organici, 2^ edizione, Casa Editrice Ambrosiana (MI), 2006.
- D. L. Pavia, G. M. Lampman et al. “Introduction to Spectroscopy”, 4th international edition, Brooks/Cole 2011.
-A. Randazzo, “Guida pratica alla interpretazione di spettri NMR”, Loghia, 2018
Laboratory:
- M. D'Ischia: "La Chimica Organica in Laboratorio." Piccin (Padova), 2002.
- R. M. Roberts, J. C. Gilbert, S. F. Martin: "Chimica Organica Sperimentale". Zanichelli Editore (BO), 1999.
- J. R. Mohrig et al. "Techniques in Organic Chemistry", 2nd ed., W.H. Freeman and Company (NY), 2006.
Teaching methods
The educational activities include lessons, classroom exercises and laboratory experiences.
The lessons will deal, with a traditional approach, with the theoretical concepts of IR and NMR spectroscopies and of mass spectrometry and, in active-learning modality, with the explanation of the lab experiences. Attendance to the latter lessons is mandatory.
The classroom exercises will be devoted to the identification of organic molecules starting from spectroscopical data.
In the lab, the students will perform the synthesis of organic molecules and will be assisted by the course teacher, by the lab technicians and by senior tutors. The students will work in couples if allowed by the anti-covid regulations, otherwise individually. Before the beginning of each lab the students are required to hand in the pre-lab questions available on the Elly platform. At the end of the course the students will have to write and hand in a report of the lab experiences.
Assessment methods and criteria
The evaluation is made up of three parts:
1) evaluation of the laboratory activities, which includes the pre-lab questions, the lab notebook (that must be handed in at the end on the course) and the execution of the last lab experience where the students are required to perform autonomously an organic reaction;
2) a 2-hours written exam, during which the student will identify an unknown compound starting from spectroscopic data;
3) an oral exam, in which the student must demonstrate to be able to:
- critically discuss one of the lab experiences, highlighting the correlation between the experimental procedure and the molecular processes;
- demonstrate the knowledge and understanding of the theory of the spectroscopy techniques;
- correlate the molecular structure of an organic compound with its 1H and 13C NMR spectrum.
Each part will be marked 0-30.The final mark will be obtained by the weighted average of the marks of the three parts (the oral and written exams will make up the 40% each of the final mark, the lab activity the 20%). The “lode” will be accorded in case the student obtains the maximum in each part together with the appropriate use of the scientific language.
Other information
In the lab, students are required to wear a lab-coat, goggles, and shoes. Moreover, to attend the lab experiences, students must have passed the safety course.
The teacher is available for additional explanations every day. It is advisable to request an appointment by email.
2030 agenda goals for sustainable development
