PRINCIPLES OF ORGANIC SYNTHESIS
Academic year and teacher
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- Versione italiana
- Academic year
- 2022/2023
- Teacher
- CLAUDIO TRAPELLA
- Credits
- 6
- Didactic period
- Primo Semestre
- SSD
- CHIM/06
Training objectives
- Princples of Organic Synthesis
Training objectives
The aim of the course consists in providing the basis for a rational approach to the synthesis of organic compounds.
The main knowledge to be acquired will be:
- elements and development of the retrosynthetic analysis as methodology for planning the synthesis of an organic product.
-The course deals with the properties and synthesis of heterocyclic compouns with a particular enphasis to the organometallic chemistry associated to the synthesis of heterocyclic molecules. The course will be divided in two fundamental parts, the first one of about 14 hours and the second one of about 22 hours of frontal lessons. During the first part of the course the students will be introduced to the synthesis of 5 and 6 member heterocyclic rings and the fundamental rule for the formation of heterocycle. During the second part of the course we will take into accont the most important organometallic reactions for the formation of heterocyclic rings.
The knowledge that will be acquired are the reactivity forecast of a heterocyclic compound in organic synthesis , the procedures and rules for the synthesis of 5 and 6 member ring heterocyclic compounds. The skills that the student must acquire are the ability to organize a multi-stage synthesis for the preparation of heterocyclic compounds and their use in the synthesis of pharmaceutical and industrial interest products. Prerequisites
- Prerequisites
The following concepts and knowledge provided by the courses of "Organic Chemistry " are required:
- syntheses and transformations of functional groups.
- organic reactions and their mechanisms Course programme
- Course programme
The course forecasts 36 hours of registered lessons uploaded in classroom.
Retro-synthetic analysis and synthesis of simple organic compounds (26 hours).
The reasons to carry out a synthesis. Historical development of organic synthesis: science or art?
Convergent synthesis, linear multistep synthesis and overall yield. Target oriented synthesis, the retro-synthetic analysis: lexicon and symbols, donor synthons, acceptor synthons, synthetic equivalent, umpolung, guidelines to the identification of useful disconnections. Disconnections of monofunctional and difunctional compounds. Strategy of carbonyl disconnections. Disconnections of saturated and aromatic heterocycles. Learning from research papers.
Properties and synthesis of five and six member heterocyclic ring, the anomeric effect. Pyridine as example for understanding the different reactivity between aromatic heterocycle and benzene. (6h) The Thorpe rule, the Baldwin rule, cycloaddiction in particular copper catalyzed (Huisgen).(6h) Making heterocycle by nucleophylic substitution, Suzuki, Neghisi and Sonogashira reaction for making heterocyclic ring. (8h) The Heck reaction and the apto number of palladium complex.
IUPAC nomenclature of fused heterocyclic ring. (8h) The catalytical cycle of palladium chemistry, differences between different reaction conditions. The importance of palladium ligands for the formation of new carbon-carbon bond. (8h) Didactic methods
- Didactic methods
The course is organized as follow:
- video lessons uploaded in classroom and clarifying focus group. Learning assessment procedures
- Learning assessment procedures
The level of achievement of the learning objectives of the course will be verified with an oral exam.
Oral examination, about 30 minutes long, will focus on the retrosynthetic analysis of one products target proposed by the teacher, discussion about the heterocyclic properties and organotransition metal chemistry characteristics. Due to the pandemic emergency the exam could be held trough Google meet, 15 multiple choice questions in 30 minutes. Reference texts
- Reference texts
Teacher’s handouts.
Stuart Warren- Organic Synthesis: The Disconnection Approach- John Wiley Sons.
PJ,A. Joule; K. Mills, Hetrocyclic Chemisrtry 5th edition, Wiley
J.J Li and G.W. Gribble, Palladium in heterocyclic chemistry, volume 20. Pergamon press.
