ORGANIC CHEMISTRY
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- Versione italiana
- Academic year
- 2022/2023
- Teacher
- ALESSANDRO MASSI
- Credits
- 6
- Didactic period
- Primo Semestre
- SSD
- CHIM/06
Training objectives
- The aim of this course is to describe the advanced principles of the organic chemistry and to facilitate its study through dedicated experimental activities. The course, in fact, consists in 4 CFU of frontal lessons and 2 CFU of laboratory activity .
The main acquired knowledge will involve:
- reaction mechanisms;
- catalysis (metal- and organo-catalysis);
- asymmetric synthesis;
- laboratory techniques for the synthesis and purification of organic molecules;
The basic acquired abilities (that are the capacity of applying the acquired knowledge) will be:
-understanding and designing of new (stereo)stereoselective catalytic reactions
- utilizing the modern experimental techniques in the filed of asymmetric synthesis under safe conditions;
- writing up of a lab book in an effective manner. Prerequisites
- Basic knowledge of Organic Chemistry: reactivity of functional groups; reaction mechanism of fundamental reactions; main spectroscopic techniques for the characterization of organic molecules; theoretical and practical knowledge of the basic operations in the laboratory of Organic Chemistry.
Course programme
- During the 32 hours of frontal lessons, the following topics are presented:
- Experimental methods in the mechanistic investigation (10 hours): non kinetic methods (products analysis, intermediates identification, stereochemical outcome, crossover experiments, isotopic labeling; kinetic methods (reaction progress kinetic analysis, kinetic isotope effects, reaction with participation of vicinal groups); structure-reactivity relationship (tension effect, steric effect, conformational effect, stereoelectronic effect).
- Chemoselectivity, diastereoselectivity, stereoselectivity (14 hours): carbonyl groups reduction, catalytic hydrogenation, selective reaction of function groups, oxidizing agents, stereospecific reactions of alkenes, prochirality, stereoselective additions to carbonyl groups, chelation, chiral auxiliaries, internal and external asymmetric induction, multicomponent reactions.
- Asymmetric Organocatalysis AO (8 hours): AO: definitions and basic concepts; asymmetric Lewis base organocatalysis; modes of activation commonly used in organocatalysis, asymmetric amino- and Brønsted acid catalysis in the carbonyl domain, aminocatalysis, asymmetric enamine catalysis, nucleophilic addition by enamine catalysis, nucleophilic substitution by enamine catalysis, asymmetric iminium catalysis, Brønsted acid catalysis, carbonyl activation by Lewis acid, double- and single hydrogen-bond donor catalysts, multiple cascade processes, SOMO organocatalysis, photoredox organocatalysis, umpolung catalysis (polarity reversal).
The laboratory activity (24 hours) deals with the following experiences:
- chemoselective reduction of 3-nitroacetophenone;
- benzoin reaction catalyzed by azolium salts;
- Stetter reaction with benzil;
- Wittig olefination with a stabilized phosphorane;
- synthesis of a 3,4-dihydropyrimidinone (Biginelli reaction);
- addition of phenylmagnesium bromide to ethyl acetoacetate ethylene ketal. Didactic methods
- The course of Organic Chemistry uses multi-modal systems: conventional (blackboard), slides and molecular building systems.
During the laboratory experiments, the students are requested to provide for the personal laboratory coat. Other personal protective equipment and all the materials necessary for the execution of the experiences are provided by the teacher. Each student is also provided of a copy of the experimental procedure (already explained in class) of the experience Absence to a maximum of two afternoons at laboratory experiences is admitted upon presentation of a justified reason. Learning assessment procedures
- The final examination consists in an oral exam (lasting about 45 min ), where it will be assessed the degree of knowledge of the topics covered during the lectures and laboratory activities as well as the ability to use this knowledge. The exam is passed with a minimum of 18 points out of 30.
Reference texts
- - Slides and material given by the teacher
- Clayden J.; Greeves, N.; Warren, S.;Wothers, P. “Organic Chemistry” ed. Oxford University Press
- Pavia D. L.; Lampman G. M.; Kris G.S. “Il laboratorio di chimica organica” ed. Sorbona
