Learning objectives
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 2;
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-Vis, IR, NMR and MS data.
5. acquiring the most important chromatographic techniques for the purification and characterization of organic compounds.
6. practice some basic bibliographic researches.
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.
UV-vis and IR Spectroscopy: principles and investigation of different classes of organic molecules.
NMR Spectroscopy: review of the main concepts studied in the previous laboratory course.
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.
Instrumental chromatographic techniques in organic chemistry.
Primary and secondary bibliographic chemistry resources. Databases and software used for bibliographic researches for the synthesis of organic compounds.
Laboratory Experiences
• 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
Bibliography
Suggested readings:
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.
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.
Teaching methods
Classroom activities: determination of the structure of simple organic molecules using 1H and 13C NMR, IR, UV and MS data.
Laboratory activities: synthesis and characterization of organic substances.
Assessment methods and criteria
The final examination will include a written part in which the candidates 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 candidates will be enquired on the theoretical topics discussed during the first part of the course.
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.
