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.
This will enable the student to acquire the ability to understand the relationship between structure and physical and chemical properties of the principal classes of organic compounds.
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
Knowledge of the contents of the General and Inorganic Chemistry course and of the Organic Chemistry and Laboratory I course.
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 gaschromatography/
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.
