SYNTHESIS STRATEGIES MODERN IN ORGANIC CHEMISTRY
Learning outcomes of the course unit
The aim of the course is to give to the students the tolls to efficiently design the synthesis of complex organic compounds on the light of the present requirement of the environmentally acceptable chemistry.
At the end of the course the student will know the modern advanced strategies of the organic chemistry related with the environmental issues (i.e. catalysis, atom efficiency, sustainable technologies, etc).
The student will be able to write the disconnection approaches of organic molecules after having find out the relations between the functional groups and to design the best synthesis through catalytic approaches exploiting not only his/her knowledges of organic chemistry but also those of the environmentally acceptable synthesis learnt during the course.
He will be able to evaluate in a judgmental manner his knowledges and will achieve the skill to find out the best disconnection analysis and then the best synthetic route by planning the experimental activity, evaluating the procedures and the environmental issues by using also the information from the literature.
The student will achieve not only the ability to communicate by using a proper scientific language the chemical and scientific problems with the experts of the area but also that of interact with people in multidisciplinary projects.
Finally the student will be able to critically analyse the experimental results with the aim of obtaining the best chemical synthesis on the basis of the best disconnection approach developed on the light of the laboratory experimental results; he will achieve the ability to correlate the topics of the course with those of the other main courses of the industrial chemistry degree.
It is requested the have attended the Organic Chemistry I and Organic Chemistry II courses and the related Laboratory courses.
Course contents summary
Organic synthesis in the past and the modern criteria for making green synthetic processes. Retrosynthetic analysis.
Fundamental concepts of the environmentally acceptable strategies: convergent and linear syntheses, the EQ factor, catalysis, heterogeneous catalysts, multistep and multicomponent reactions, continuous flow processes.
Order of events. One-group C-C disconnection. Disconnections 1,1-, 1,2- and 1,3-di C-X under direct and reversed polarity. One-C-C bond disconnection. Disconnection 1,1-, 1,2- and 1,3-di C-C. Sterocontrol.
Stereospecific and stereoselctive processes. Carbonyl condensation. Disconnections 1,2-, 1,3-, 1,4-, 1,5- and 1,6-di C-O. Reconnection. Approach to cyclic and not aromatic heterocyclic systems. Access to 3, 4,
5, 6 and 7 ring systems. Kinetic and thermodynamic problems involved and choice of the best synthetic route. Pericyclic reactions. Kinetic and thermodynamic control in pericyclic reactions. Orbital symmetry role in thermal and photochemical processes. Electrocyclic reactions. Sigmatropic reactions. 2+2 and 4+2 cycloaddition reactions. 1,3-dipolar cycloadditions. Application of the empirical Woodward-Hoffmann rules.
F.A. Carey, R.J. Sundberg: Advanced Organic Chemistry (3rd edition): Part B: Reactions and Synthesis; Plenum Press; 1990.
S. Warren: Organic Synthesis, The Disconnection Approach; Wiley and sons; 1982.
Oral lesson. At the end of the course will be carried out group exercises.
The slides concerning the environmentally acceptable strategies (units 1 and 2) and the pericyclic reactions (units 20 e 21) are already present on Elly platform. On the contrary, the slides concerning the disconnection strategies, prepared utilizing the Warren “Organic Synthesis - The Disconnection Approach” book are not present on Elly platform as the student have to learn to write with his own hand the disconnections processes and not simply to read them on previously printed sheets.
Assessment methods and criteria
Oral examination consisting in the written design of the disconnection and the synthesis of two target molecules and the subsequent discussion of the elaborate.
Time: from 20 to 60 minutes depending on the student skills.
Evaluation: the final mark is in thirtieths, to pass the examination at least a 18/30 mark must be obtained.
The course is organized in two parts: a theoretical part concerning the synthetic strategies and a second part with exercises concerning the synthesis of complex organic compounds.