LABORATORY FOR ORGANIC CHEMISTRY II
Learning outcomes of the course unit
The course has several aims such as :
1. practice the student ability in the laboratory; 2. practice some of the organic reactions encountered in the theoretic course of organic chemistry;
3. practice the use of IR, NMR, UV-Vis and Mass spectroscopies;
4. acquiring the ability to identify the structure of an organic compound via combined UV. IR, NMR and mass spectra.
5. acquiring the most important chromatographic techniques for purification and characterization of organic compounds.
Course contents summary
Instrumental techniques for the characterisation of the organic compounds.
NMR Spectroscopy: review of the main concepts studied in the previous laboratory course.
IR Spectroscopy: principles and application to the investigation of the different classes of the organic molecules.
Mass Spectrometry: principles and features of the main techniques. Use of the fragmentation processes occurring in the electron impact mass spectrometry for the determination of the molecular structure.
Instrumental chromatographic techniques in organic chemistry.
Exercises aimed at the determination of organic molecular structures from 1H-NMR, IR, UV and MS data.
Laboratory experiences (9-10).
• Reduction of a keton 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.
• Protection reaction of an amino acid.
• Synthesis of a Grignard reagent and reaction with an ester.
• Protection reaction of D-mannose with acetone.
• Synthesis of a dipetide.
• Synthesis of a deuterated compound.
• The compounds obtained at the end of the experiences are in general characterised also by NMR, IR, MS, and m.p.
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.
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. H. Williams, I. Fleming, "Spectroscopic Methods in Organic Chemistry" 5th Edition, McGraw-Hill, 1996.
Laboratory practice and explanation in classroom.
Assessment methods and criteria
Written examination with identification of an organic compounds via interpretation of its IR NMR and mass spectra and oral exam.