ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY

Chimica ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY

0522300036
DEPARTMENT OF CHEMISTRY AND BIOLOGY "ADOLFO ZAMBELLI"
EQF7
CHEMISTRY
2022/2023

OBBLIGATORIO
YEAR OF COURSE 1
YEAR OF DIDACTIC SYSTEM 2016
AUTUMN SEMESTER
CFUHOURSACTIVITY
756LESSONS
224EXERCISES
336LAB
ExamDate
APPELLO FEBBRAIO22/02/2023 - 09:00
APPELLO FEBBRAIO22/02/2023 - 09:00
Objectives
THE STUDENT IS EXPECTED TO AQUIRE A DEEPER KNOWLEDGE ON CLASSICAL AND MOST RECENT METHODS FOR THE REGIO- AND STEREOSELECTIVE FORMATION OF C-C AND C-HETEROATOM BONDS.
THE MAIN KNOWLEDGE ACQUIRED BY THE STUDENT WILL BE:
THE SYNTHESIS AND APPLICATION OF MG, LI AND CU-BASED ORGANOMETALLICS; THE SYNTHESIS OF ALKENES OTHER THAN VIA WITTIG REACTION; THE STEREOSELECTIVE METHODS OF OXIDATION AND REDUCTION OF ALKENES AND OTHER FUNCTIONAL GROUPS. MOREOVER, RECENT AND MODERN APPLICATION OF ONE-POT CASCADE AND MULTICOMPONENT REACTIONS FOR THE SYNTHESIS OF COMPLEX MOLECULES WILL BE ALSO ILLUSTRATED. MECHANISTIC ASPECTS OF THE REACTIONS WILL BE ALSO TREATED WHENEVER NECESSARY. SYNTHETIC EXERCISES IN THE CLASSROOM WILL HELP THE STUDENT TO IMPROVE THE KNOWLEDGE ON THE DIFFERENT TOPICS. LABORATORY WORK IN SELECTED REACTIONS WILL GIVE THE STUDENT THE OPPORTUNITY TO APPLY THE SYNTHETIC SCHEMES STUDIED.
THE MAIN SKILLS DEVELOPED BY THE STUDENT WILL BE:
TO KNOW AND DISCUSS ABOUT THE METHODOLOGIES STUDIED; TO SUGGEST THE SYNTHESIS OF RELATIVELY COMPLEX MOLECULES TAKING INTO ACCOUNT THE REGIO- AND STEREOSELECTIVITY ISSUES; TO IDENTIFY THE PROCEDURES SUITABLE TO PURIFY AND CHARACTERIZE THEM.
Prerequisites
BASIC KNOWLEDGE PREVIOUSLY AQUIRED BY THE STUDENT IN THE COURSES OF ORGANIC CHEMISTRY I AND II
Contents
THE COURSE IS DIVIDED INTO THREE MODULES:
IN MODULE A, THE TEACHING LESSONS ARE ABOUT THE FOLLOWING TOPICS: STEREOSELECTIVE ALPHA AND BETA ALKYLATION OF CARBONYL COMPOUNDS AND THEIR ALPHA,BETA-UNSATURATED COUNTERPARTS. ASYMMETRIC METHODS OF ALPHA AND BETA HETEROFUNCTIONALIZATION OF CARBONYL COMPOUNDS AND THEIR ALPHA,BETA-UNSATURATED COUNTERPARTS. ALDOL REACTION AND ASYMMETRIC VERSIONS, INCLUDING ORGANOCATALYTIC SYSTEMS. SULFUR YLIDES AND THEIR APPLICATIONS. WITTIG OLEFINATION VARIANTS, PETERSON OLEFINATION. MAGNESIUM, LITIUM AND COPPER-ORGANOMETALLIC COMPOUNDS AND THEIR APPLICATIONS. STEREOSELECTIVE OXIDATION OF ALKENES. RING-OPENING AND REARRANGEMENTS OF EPOXIDES. FUNDAMENTAL REACTIONS OF ALLYLIC AND VINYLIC ORGANOSILICON COMPOUNDS. ASYMMETRIC METAL CATALYSED HYDROGENATIONS OF OLEFINS AND METAL-FREE REDUCTIONS. ONE-POT, CASCADE AND MULTICOMPONENT REACTIONS AND SELECTIVE EXAMPLES ON THEIR APPLICATIONS FOR THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS.
IN MODULE B, RETROSYNTHETIC EXCERCISES WILL BE PRESENTED ON THE REACTIONS DISCUSSED IN MODULE A.
IN MODULE C, PRACTICAL SYNTETIC APPLICATIONS OF THE REACTIONS STUDIED IN MODULE A TO PREPARE DIFFERENT COMPOUNDS WILL BE PERFORMED IN THE LABORATORY. THE COMPOUNDS WILL BE ISOLATED AND STRUCTURALLY CHARACTERIZED.
AROUND 60% OF MODULE A IS DEVOTED TO CARBON-CARBON AND CARBON-HETEROATOM BOND FORMATION, 20% TO OXIDATION PROCESSES AND 20% TO REDUCTION AND CASCADE PROCESSES.
Teaching Methods
MODULES A AND B COMPRISE TEACHING LESSONS (86 H) AND EXERCISES AT THE BLACKBOARD IN THE CLASSROOM ON THE ORGANIC TRANSFORMATIONS DISCUSSED IN MODULE A. THE ATTENDANCE OF BOTH MODULES IS HIGHLY RECOMENDED. MODULE C (36 H) IS LABORATORY PRACTISE CONCERNING THE SYNTHESIS AND CHARACTERIZATION OF SELECTED COMPOUNDS. THE FINAL DATA OF THE LABORATORY WORK HAVE TO BE WRITTEN IN REPORTS TO DELIVER TO THE TUTOR BEFORE THE FINAL ORAL EXAMINATION. 75% ATTENDANCE OF MODULE C IS COMPULSORY.
Verification of learning
THE AIM OF THE FINAL EXAM IS TO CHECK THAT THE LEARNING OUTCOMES HAVE BEEN ACHIEVED. FORMATIVE ASSESSMENT IS CERTIFIED BY AN ORAL EXAMINATION OF AROUND 45 MINUTES, WITH A FINAL MARK EXPRESSED BETWEEN 18 AND 30, COMPRISING QUESTIONS AND DISCUSSION ABOUT THE CONTENT OF THE TEACHING COURSE AND THE LABORATORY WORK. THE ABILITY TO COMMUNICATE THE TOPICS AND TO PROPOSE A SYNTHETIC SEQUENCE OF A TARGET MOLECULE PROPOSED BY THE TEACHING EXAMINER, WILL BE ALSO ASSESSED DURING THE ORAL EXAMINATION. THE FULL MARK AND HONORS IS ACHIEVABLE WHEN THE STUDENT DEMONSTRATES HIGH ABILITY IN SCIENTIFIC LANGUAGE ON THE TOPICS OF THE COURSE AND ABILITY TO CORRELATE THE TOPICS TO OTHER INTERDISCIPLINARY ISSUES WITH EXCELLENT MASTERY
Texts
F. A. CAREY AND R. J. SUNDBERG, ADVANCED ORGANIC CHEMISTRY B AND A, (FIFTH
EDITION) SPRINGER, 2007.
J. MARCH, ADVANCED ORGANIC CHEMISTRY, J. WILEY & SONS; NEW YORK (IV ED.)
TEACHING MATERIAL ABOUT MORE RECENT DEVELOPMENTS FROM THE SCIENTIFIC LITERATURE WILL BE AVAILABLE FROM THE TUTOR.
More Information
FOR FURTHER INFORMATION SEND AN E-MAIL TO: LATTANZI@UNISA.IT
WEBPAGE: https://docenti.unisa.it/003250/en/curriculum
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