Learning objectives
The acquisition of advanced techniques for the synthesis and purification of organic compounds is obtained through an extensive laboratory practice. The compounds synthesized will be characterized with either chromatographic and spectroscopic techniques (MS, UV, IR, 1H and 13C NMR).
Course unit content
<ul>
<li>Preparation of a deuterium labelled compound: synthesis of 2-deuterated cinnamic acid.</li>
<li>Synthesis of N-acetyl-(L)-prolyl-(L)-phenylalanine methyl ester dipeptide.</li>
<li>Enantioselective reduction of trifluoroacetofenone yeasts and determination of the enatiomeric excess through GC analysis using a gas chromatographer equipped with a chiral stationary phase.</li>
<li>Derivatization of a chiral alcohol with the Mosher's acid and determination of the diasteromeric excess and of the absolute configuration through 1H NMR spectroscopy.</li>
<li>Study of the stereoselectivity of a aldohol condensation reaction under thermodynamic and kinetic control.</li>
</ul>
Bibliography
Pratica di Laboratorio:<br />
* M. D'Ischia: "La Chimica Organica in Laboratorio", Piccin (PD), 2002.<br />
* R.M. Roberts, J.C. Gilbert, S.F. Martin: "Chimica Organica Sperimentale", Zanichelli (BO), 1998.<br />
* M. Casey, J. Leonard, B. Lygo, G. Procter: " Advanced Practical Organic Chemistry", 2nd Edition, Stanley Thornes Ltd (UK), 1998.<br />
<br />
Spettroscopia:<br />
* G.F. Pedulli: “Metodi fisici in Chimica Organica", Piccin (PD), 1996.<br />
* R. M. Silverstein, F. X. Webster, D. J. Kiemle: “Identificazione spettrometrica di composti organici, 2^ edizione, Casa Editrice Ambrosiana (MI), 2006.<br />
* D. H. Williams, I. Fleming: "Spectroscopic Methods in Organic Chemistry" 5th Edition, McGraw-Hill, 1996.<br />
