28960 - Laboratory of Sustainable Methodologies in Organic Chemistry L

Learning outcomes

After completing this course the student has the knowledge on methodologies for conducting reactions leading to reduced environmental impact and to measure some of the major environmental indicators associated with them. In particular, it is able to: critically choose the appropriate experimental conditions, identify and assess hazards associated with substances used; find information related to the risks of the substances used, apply the principles of Green Chemistry in the execution of organic reactions, use of alternative solvents to VOCs and reagents from renewable sources and introduce elements of environmental efficiency in the design of organic reactions, calculate, through some simple software applications, some of the environmental indicators associated with organic reaction.

Course contents

The program of the course starts from the knowledge acquired in the course of  Laboratory of Organic Chemistry. It is formed by two parts. The first one concerns basic informations and principles of spectroscopy  (NMR, IR) and mass spectrometry (GC-MS) applied to the investigations of properties and structure of pre-synthesized materials.

The second part of course concerns the practical preparations of  some organic compounds, in parallel to subjects discussed in the courses of Organic Chemistry and Sustainable Methodologies in Organic Chemistry

The proposed experience are as follows:

1 - Williamson synthesis of  2-ethoxynaphthalene using microwawe irradiation;

2 - a greener approach to Aspirin: synthesis using microwawe irradiation;

3 - [2+2] cycloaddition under photochemical conditions;

4 - synthesis of  2-methilbenzimidazole using microwawe irradiation;

5 - organometallic reactions in aqueous media: Indium-promoted addition to benzaldehyde;

6 - Michael addition  by transfer phase catalysis (TPC);  

7 - aldolic condensation without solvent;

8 - Wagner-Meerwein rearrangement in homochiral molecule using microwawe irradiation.

Readings/Bibliography

M.C. Cann and M.C. Connelly, Real-World. Cases in Green Chemistry, American Chemical Society.1998.

Greener Approches to Undergraduate Chemistry Experiments. American Chemical Society.

R.M. Silverstein et altri, Identificazione Spettrometrica di Composti Organici, Casa Editrice Ambrosiana.

Teaching methods

Detailed synthetic procedures will be furnished to each student, together with mechanistic explanation of the considered reactions and NMR spectra of starting materials and final products. In the laboratory there are working places with suitable equipments to perform the considered reactions.

Assessment methods

The Assessment will be performed simultaneously with Sustainable Methods in Organic Chemistry. Students will discuss the mechanisms of reactions that led to the formation of their products, the spectroscopic recognition of them, and finally they must discuss the environmental impact of the used procedures.

Teaching tools

Copies of slides reported in class room will be fournished and, also, copies of NMR and MS spectra of products synthesized and classroom exercises NMR and mass spectroscopy.

Office hours

See the website of Andrea Mazzanti