LABORATORY FOR ORGANIC CHEMISTRY II
Learning outcomes of the course unit
1) To improve the ability of students in the laboratory practice;
2) To furnish a practical approach to the theoretical aspects of organic chemistry studied in the parallel course Chimica Organica 2;
3) To give theoretical and practical knowledges relative to IR spectroscopy and Mass spectrometry to be related and joint to those relative to NMR and UV-vis spectroscopies studied in the previous courses;
4) To make able the students to identify and characterise the structure of a known or unknown organic compound through spectroscopic and spectrometric data.
In order to fruitfully follow the course, it is important to follow the parallel course of Chimica Organica 2. Furthermore it is necessary to have previously followed the courses of Chimica Organica 1 and Laboratorio di Chimica Organica 1
Course contents summary
Theoretical part: Instrumental techniques for the characterisation of organic compounds. NMR Spectroscopy: review of the main concepts studied in the previous laboratory course of organic chemistry. IR Spectroscopy: principles and application to the investigation of the different classes of 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 a molecular structure.
Exercises aimed at the determination of organic molecular structures from 1H-NMR, IR, UV and MS data.
Explanation of the laboratory experiences.
Laboratory practical part: 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. N- and/or C-protection reaction of an amino acid. Synthesis of a Grignard reagent and reaction with an ester. Protection reaction of D-mannose with acetone. Mutarotation process of glucose aqueous solutions. Detection of the solubility properties of proteins and their hydrolysis.
Compounds obtained at the end of the experiences are in general characterised by NMR, IR, MS, determination of m.p. and specific optical rotation.
a) M. D'Ischia: 'La Chimica Organica in Laboratorio.' Piccin (Padova) 2002.
b) R.M. Roberts, J.C. Gilbert, S.F. Martin: 'Chimica Organica Sperimentale'. Zanichelli Editore (BO), prima edizione 1999.
c) R. M. Silverstein, F.X. Webster: 'Spectrometric identification of organic compounds'. Wiley.
Other suggested Textbook:
a) B.S. Furniss, A.J. Hannaford, P.W.G. Smith, A.R. Tatchell: 'Vogel's Textbook of Practical Organic
Chemistry-5th Edition'. Longman Scientific & Technical (Harlow, UK), 1989.
b) M. Casey, J. Leonard, B. Lygo, G. Procter: 'Advanced Practical Organic Chemistry'. Blackie (Glasgow and London, UK) 1990.
c) G. F. Pedulli, 'Metodi Fisici in Chimica Organica', Piccin Nuova Libraria (Padova)
Theoretical and practical teaching in classroom and laboratory practical session