LABORATORY FOR ORGANIC CHEMISTRY II
Learning outcomes of the course unit
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 mechanism of the reactions performed in the lab; understand the chemical processes that occur at every step of the experimental procedure (knowledge and understanding);
- In the lab, prepare and purify an organic compound through simple methodologies working according to the safety guidelines; choose the appropriate methodology to ascertain the identity and the purity of the synthesized compounds; correlate the structure, physical properties and reactivity of the main classes of organic compounds; 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);
- Write a laboratory notebook (communication skills);
- Evaluate the risk related to the reactants and procedures used in the lab (making judgements);
- Establish the experimental procedure to carry out an organic synthesis (learning skills).
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 contents summary
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.
IR Spectroscopy: principles and investigation of different classes of
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.
• Reduction of a ketone with sodium borohydride.
• Preparation of a Grignard reagent and synthesis of a tertiary alchol.
• Aldol condensation.
• 1,4-Addition reaction to an alfa,beta-unsaturated compound.
• Synthesis of a deuterated compound through Knoevenagel
• Protection reaction of D-mannose with acetone.
- 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
- 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.
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 be assisted by the course teacher, by the lab technicians and by senior tutors. The students will work in couples. Before the beginning of each lab the students are required to hand in the pre-lab questions available on the Elly platform, that will be evaluated.
The slides of the lessons will be uploaded every week on the Elly website. To download the slides registration on the website is required.
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;
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.
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.