ADVANCED ORGANIC CHEMISTRY
Academic year and teacher
If you can't find the course description that you're looking for in the above list,
please see the following instructions >>
- Versione italiana
- Academic year
- 2022/2023
- Teacher
- VINICIO ZANIRATO
- Credits
- 9
- Didactic period
- Primo Semestre
- SSD
- CHIM/06
Training objectives
- Knowledge:
Students will have to acquire a deep knowledge of molecular structures, stereochemistry, physical properties and reactivity of organic compounds which are object of study.
Skills:
a) Students will have to be able to relate molecular structure with physical and chemical properties;
b) Students will have to be able to explain and drawing the reaction mechanisms;
c) Students will have to be able to predict the progress of a reaction on the basis of the structure of reagents and reaction conditions. Prerequisites
- Basic knowledge of General Chemistry and Organic Chemistry (preparatory teaching to the course of Advanced Organic Chemistry).
Course programme
- The course is scheduled for a total amount of 76 hours of whom 64 are frontal lectures and 12 are guided tutorial in labs.
Amines: physical and chemical properties. [2 + 4 h].
Amino acids. Isoelectric point. Peptide linkage. Protein structures. Lipids. [4 h].
Carbohydrates. O- and N-Glycosides. Di- and polysaccarides. Nucleosides and nucleotides. [4 h].
Formation and reactions of enols and enolates: alkylation and condensation reactions. Enamines, Silyl enol ethers. Carbonyl “Umpolung” reagents. [19 h].
Aromatic compounds: reactions with electrophiles and with nucleophiles. Palladium catalyzed coupling reactions. Aromatic heterocycles: nomenclature, syntheses and reactions. [17 h].
Peryciclic reactions: cycloadditions, sigmatropic and electrocyclic reactions. [15 h].
Rearrangements: migration to electron-deficient C, O and N. [7 h].
Pratical Exercitations:
Claisen-Schmidt condensation: synthesis of dibenzylideneacetone;
Weitz-Scheffer epoxidation: synthesis of chalcone oxide;
NaBH4 carbonyl reduction: synthesis of benzhydrol.
[12 hours]. Didactic methods
- The course is organized as follows: frontal lectures with the aid of blackboards and a slide projector. Students are given in advance an electronic outline of the topics which will be treated during each lecture; this will have to be integrated with personal notes so as to build up course material usable for studying. During lectures students are invited to make their own contribution by giving hints and ideas for the analysis and improvements of the concepts explained.
Learning assessment procedures
- The oral exam has the aim of testing the level of the learning objectives previously described. In order to pass the exam students have to show they are able to correctly write formulas and reaction mechanisms on the blackboard. Additional evaluation criteria are: the ability of comparing and connecting different topics; the ability of answering the questions in a clear and accurate way while using specific vocabulary.
Reference texts
- Teacher’s handouts.
Chimica Organica - W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote - V edizione EdiSES.
Follow-up materials: ORGANIC CHEMISTRY - J. Clayden, N. Greeves, S. Warren - Second Edition - OXFORD University Press.
Solutions manual to accompany ORGANIC CHEMISTRY - J. Clayden, S. Warren – Second Edition - OXFORD University Press.
