27708 - Laboratory of Organic Chemisty II L (A-L)

Learning outcomes

During the course Laboratory of Organic Chemistry II, students will be request to perform eight reactions, which will be explained in the course of Organic Chemistry II. Students will record the H and C NMR and FT-IR  spectra and make analysis by GC-MS and HPLC of prepared samples.   

Course contents

The program of the course starts from the knowledge acquired in the course of  Laboratory of Organic Chemistry I. 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. Several dedicated instruments are available to direct use of students.

The second part of course concerns the practical preparations of  eight products, in parallel to subjects discussed in the course of Organic Chemistry II.

The proposed experience are as follows:

1 - reaction of reduction (by metal hydrides) of a stereogenic carbon in a homochiral molecule;

2 - aldolic condensation involving kinetic and thermodinamic enolates;

3 - Michael addition and Claisen condensation. Proton acydity in alfa position to a carbonyl group;

4 - Wagner-Meerwein trasposition in homochiral molecule; 

5 - intramolecolar SN2  reaction: synthesis of homochiral oxirane;

6 - Wittig reaction and related reactions. Synthesis of  conjugated diene;

7 - synthesis by transfer phase agents;

8 - synthesis of  2-methilbenzimidazole (mesomerism and tautomerism).

Readings/Bibliography

W.H. Brown et altri, Chimica Organica, 5e (2011) EdiSES-Napoli.

M. D'Ischia, La Chimica Organica in Laboratorio, Casa Editrice Piccin.

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

Teaching methods

Detailed synthesis procedures will be fornished to each student, together with mechanicistic explanation of the considered reactions and NMR spectra of starting materials and final products.

In the laboratory there are working places with suitable equipemments to perform the considered reactions.

Assessment methods

Students are request to have an oral examination at the same time of the examination of course Organic Chemistry II. Subjects of the examination will be the reaction mechanisms of tha studied reations and the characterization of the obtained products.

Students are request to write detailed reports on all programmed experiences.

Teaching tools

Copies of all slides reported in class room will be fournished

Office hours

See the website of Claudio Paolucci