ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY

Alessandra LATTANZI ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY

0522300036
DEPARTMENT OF CHEMISTRY AND BIOLOGY "ADOLFO ZAMBELLI"
EQF7
CHEMISTRY
2017/2018

OBBLIGATORIO
YEAR OF COURSE 1
YEAR OF DIDACTIC SYSTEM 2016
PRIMO SEMESTRE
CFUHOURSACTIVITY
756LESSONS
224EXERCISES
336LAB
Objectives
THE STUDENT IS EXPECTED TO ACQUIRE A DEEPER KNOWLEDGE ON RECENT METHODS FOR THE STEREOSELECTIVE FORMATION OF C-C AND C-HETEROATOM BONDS; 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, APPLICATION OF ONE-POT CASCADE AND MULTICOMPONENT REACTIONS, TAKEN FROM THE RECENT LITERATURE, FOR THE SYNTHESIS OF COMPLEX MOLECULES WILL BE ILLUSTRATED. MECHANISTIC ASPECTS OF THE REACTIONS WILL BE ALSO TREATED WHENEVER NECESSARY. AT THE END OF THE COURSE THE STUDENT WILL BE ABLE TO SUGGEST THE SYNTHESIS OF RELATIVELY COMPLEX MOLECULES. LABORATORY PRACTISE IN SELECTED REACTIONS AND SYNTHETIC EXCERCISES WILL BE INTEGRATED MODULES OF THE COURSE.
Prerequisites
NO FORMAL PREREQUISITIES ARE NECESSARY TO ATTEND THIS COURSE, AS ORGANIC CHEMISTRY I AND II WERE PREVIOUSLY PASSED EXAMINATIONS
Contents
THE COURSE IS DIVIDED INTO THREE MODULES:
IN MODULE A THE TEACHING LESSONS ARE ABOUT THE FOLLOWING ARGUMENTS: STEREOSELECTIVE ALPHA ANDN BETA ALKYLATION OF CARBONYL COMPOUNDS. ASYMMETRIC METHODS OF ALPHA AND BETA HETEROFUNCTIONALIZATION OF CARBONYL COMPOUNDS. ALDOL REACTION AND ASYMMETRIC VERSIONS. SULFUR YLIDES AND THEIR APPLICATIONS AND WITTIG VARIANTS FOR OLEFINATION, PETERSON OLEFINATION. MAGNESIUM, LITIUM AND COPPER-ORGANOBASED COMPOUNDS. STEREOSELECTIVE OXIDATION OF ALKENES. RING-OPENING AND REARRANGEMENTS OF EPOXIDES. NODS ON ORGANOSILICON AND ORGANOBORON COMPOUNDS. ASYMMETRIC METAL CATALYSED HYDROGENATIONS OF OLEFINS AND METAL-FREE REDUCTIONS. ONE-POT, CASCADE AND MULTICOMPONENT REACTIONS. 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 REACTIONS TO PREPARE DIFFERENT COMPOUNDS WILL BE PERFORMED IN THE LABORATORY.
Teaching Methods
MODULES A AND B COMPRISE TEACHING LESSONS (86 H) AND EXCERCISES AT THE BLACKBOARD IN THE CLASSROOM. MODULE C (36 H) IS LABORATORY PRACTISE, 75% ATTENDANCE 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 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 WILL BE ALSO ASSESSED.
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 WILL BE AVAILABLE FROM THE TUTOR.
More Information
FOR FURTHER INFORMATION SEND AN E-MAIL TO: LATTANZI@UNISA.IT
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