Learning objectives
Knowledge and understanding
The aim of the course is to provide the students: a) the basic theoretical knowledge for the structural determination of simple organic compounds by using several spectroscopic techniques and b) the theoretical and practical aspects of the synthetic methodologies learnt during the course of organic chemistry II.
Applying knowledge and understanding
The student will be able to realize autonomously the preparation and purification of an organic compound by applying common and simple synthetic methodologies and to identify its structure through the interpretation of the corresponding MS, UV, IR and NMR (1H and 13C) spectra.
Prerequisites
- - -
Course unit content
Survey of the common instrumental techniques for the characterization of organic compounds, in particular: UV-Vis, IR and NMR spectroscopy, mass spectrometry and instrumental chromatographic techniques in organic chemistry. Determination of the structure of simple organic molecules using 1H and 13C NMR, IR, UV and MS data. Synthesis and characterization of organic substances (laboratory experiences).
Full programme
The safety in the organic chemistry lab.
IR Spectroscopy: principles and investigation of different classes of organic molecules.
NMR Spectroscopy: review of the main concepts studied in the previous laboratory course, 13C spectroscopy, advanced aspects of spin-spin coupling; dynamic NMR.
Mass Spectrometry: principles and features of the main ionization techniques. Use of the fragmentation processes occurring in the electron impact mass spectrometry for the determination of the molecular structure.
Determination of organic molecular structures from 1H-NMR, IR, UV-vis and MS data.
Primary and secondary bibliographic chemistry resources. Databases and software used for bibliographic researches for the synthesis of organic compounds.
Laboratory Experiences
• Reduction of a ketone with sodium borohydride and purification of the product by high vacuum distillation.
• Aldol condensation and characterisation of the product by gas-chromatography/mass spectrometry.
• 1,4-Addition reaction to an alfa,beta-unsaturated compound.
• Synthesis of a deuterated compound through Knoevenagel condensation.
• Protection reaction of D-mannose with acetone.
• Protection reaction of an amino acid with CBz protecting group
• Synthesis of a dipetide.
Bibliography
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.
G. M. Lampman, D. L. Pavia, G. S. Kriz, J. R. Vyvyan, "Spectroscopy", 4th ed (international edition), Brooks/Cole - CENGAGE learning, 2010.
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), prima edizione 1999.
J. R. Mohrig et al. "Techniques in Organic Chemistry", 2nd ed., W.H. Freeman and Company, NY, 2006.
K. L. Williamson, K. M. Masters, "Organic Experiments: macroscale and microscale", 6th ed (international edition), Brooks/Cole - CENGAGE learning, 2011.
Teaching methods
Classroom activities: basic theoretical aspects of IR and NMR spectroscopy and mass spectrometry (electron impact); exercises for the interpretation of 1H and 13C NMR, IR, UV and MS spectra for the determination of the structure of simple organic molecules.
Laboratory activities: seven lab experiences of synthesis and characterization of organic substances.
Assessment methods and criteria
The final examination will include a written part in which the students have to determine the structure of a unknown organic compounds using NMR (1H and 13C), UV-vis, IR and MS data.
In the following oral part, the student will be enquired on the theoretical topics discussed during the first part of the course.
Editing of a personal lab booknote is also requested.
Other information
The format of the class will be lectures of one or two hours each spread over two mornings per week.
The laboratory training will be articulated in 7 experiences of four hours each held weekly.
