Chimica | ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY

cod. 0522300036

ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY

	0522300036
	DEPARTMENT OF CHEMISTRY AND BIOLOGY "ADOLFO ZAMBELLI"
	EQF7
	CHEMISTRY
	2018/2019

CURRICULUM BIOMOLECULAR CHEMISTRY

	OBBLIGATORIO
	YEAR OF COURSE 1
	YEAR OF DIDACTIC SYSTEM 2016
	PRIMO SEMESTRE

TEACHING UNITS

SSD	CFU	HOURS	ACTIVITY	TYPE OF ACTIVITY
CHIM/06	7	56	LESSONS	COMPULSORY SUBJECTS, CHARACTERISTIC OF THE CLASS
CHIM/06	2	24	EXERCISES	COMPULSORY SUBJECTS, CHARACTERISTIC OF THE CLASS
CHIM/06	3	36	LAB	COMPULSORY SUBJECTS, CHARACTERISTIC OF THE CLASS

PROFESSORS

	ALESSANDRA LATTANZI T Curriculum
	LAURA PALOMBI Curriculum

	Objectives
	THE STUDENT IS EXPECTED TO AQUIRE A DEEPER KNOWLEDGE ON CLASSICAL AND MOST RECENT METHODS FOR THE REGIO- AND STEREOSELETIVE 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 EXCERCISES IN THE CLASSROOM WILL HELP THE STUDENT TO IMPROVE THE KNWOWLEDGE ON THE DIFFERENT TOPICS. LABORATORY PRACTISE 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.

THE STUDENT IS EXPECTED TO AQUIRE A DEEPER KNOWLEDGE ON CLASSICAL AND MOST RECENT METHODS FOR THE REGIO- AND STEREOSELETIVE 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 EXCERCISES IN THE CLASSROOM WILL HELP THE STUDENT TO IMPROVE THE KNWOWLEDGE ON THE DIFFERENT TOPICS. LABORATORY PRACTISE 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
	KNOWLEDGE OF ORGANIC CHEMISTRY I AND II COURSES AND SPECTROSCOPIC BASIC TECHNIQUES PREVIOUSLY AQUIRED AT BACHELOR DEGREE.

	Contents
	THE COURSE IS DIVIDED INTO THREE MODULES: IN MODULE A (7CFU) THE TEACHING LESSONS ARE ABOUT THE FOLLOWING ARGUMENTS: REGIOSELECTIVE ALKYLATION OF CARBONYL COMPOUNDS. STEREOSELECTIVE ALPHA AND BETA ALKYLATION OF CARBONYL COMPOUNDS VIA CHIRAL AUXILIARES. 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. SYNTHESIS AND APPLICATIONS OF MAGNESIUM, LITIUM AND COPPER-ORGANOBASED COMPOUNDS. EPOXIDES SYNTHESIS,STEREOSELECTIVE OXIDATION OF ALKENES, EPOXIDES RING-OPENING AND REARRANGEMENTS. BRIEF INTRODUCTION ON ORGANOSILICON 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 AND SOLVED BY STUDENTS IN THE PRESENCE OF THE TUTOR. IN MODULE C, PRACTICAL SYNTETIC APPLICATIONS OF REACTIONS TO PREPARE DIFFERENT COMPOUNDS WILL BE PERFORMED IN THE LABORATORY, FOLLOWED BY PURIFICATION AND CHARACTERIZATION OF THE FINAL PRODUCTS.

Contents

THE COURSE IS DIVIDED INTO THREE MODULES:
IN MODULE A (7CFU) THE TEACHING LESSONS ARE ABOUT THE FOLLOWING ARGUMENTS: REGIOSELECTIVE ALKYLATION OF CARBONYL COMPOUNDS. STEREOSELECTIVE ALPHA AND BETA ALKYLATION OF CARBONYL COMPOUNDS VIA CHIRAL AUXILIARES. 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. SYNTHESIS AND APPLICATIONS OF MAGNESIUM, LITIUM AND COPPER-ORGANOBASED COMPOUNDS. EPOXIDES SYNTHESIS,STEREOSELECTIVE OXIDATION OF ALKENES, EPOXIDES RING-OPENING AND REARRANGEMENTS. BRIEF INTRODUCTION ON ORGANOSILICON 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 AND SOLVED BY STUDENTS IN THE PRESENCE OF THE TUTOR.
IN MODULE C, PRACTICAL SYNTETIC APPLICATIONS OF REACTIONS TO PREPARE DIFFERENT COMPOUNDS WILL BE PERFORMED IN THE LABORATORY, FOLLOWED BY PURIFICATION AND CHARACTERIZATION OF THE FINAL PRODUCTS.

	Teaching Methods
	MODULES A AND B COMPRISE TEACHING LESSONS AT THE BLACKBOARD AND EXCERCISES AT THE BLACKBOARD IN THE CLASSROOM (86 H). MODULE C (36 H) IS LABORATORY PRACTICE, 75% ATTENDANCE IS COMPULSORY. DURING THE LABORATORY SYNTHETIC SEQUENCES WHERE THE STUDENT WILL APPLY THE CONCEPTS STUDIED IN THE MODULES A AND B. AT THE END OF THE LABORATORY PRACTICE THE STUDENT HAS TO WRITE A SCIENTIFIC REPORT ON THE SYNTHESES PERFORMED IN THE LABORATORY TO BE DELIVERED TO THE LABORATORY TUTOR BEFORE ATTENDING THE EXAM.

Teaching Methods

MODULES A AND B COMPRISE TEACHING LESSONS AT THE BLACKBOARD AND EXCERCISES AT THE BLACKBOARD IN THE CLASSROOM (86 H). MODULE C (36 H) IS LABORATORY PRACTICE, 75% ATTENDANCE IS COMPULSORY. DURING THE LABORATORY SYNTHETIC SEQUENCES WHERE THE STUDENT WILL APPLY THE CONCEPTS STUDIED IN THE MODULES A AND B. AT THE END OF THE LABORATORY PRACTICE THE STUDENT HAS TO WRITE A SCIENTIFIC REPORT ON THE SYNTHESES PERFORMED IN THE LABORATORY TO BE DELIVERED TO THE LABORATORY TUTOR BEFORE ATTENDING THE EXAM.

	Verification of learning
	THE AIM OF THE FINAL EXAM IS TO CHECK THAT THE LEARNING OUTCOMES HAVE BEEN ACHIEVED. THE STUDENT CAN BE EVALUATED ONLY AFTER HAVING DELIVERED THE REPORTS OF RESULTS ON THE EXPERIMENTAL WORK DONE IN THE LABORATORY MODULE. 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.

Verification of learning

THE AIM OF THE FINAL EXAM IS TO CHECK THAT THE LEARNING OUTCOMES HAVE BEEN ACHIEVED. THE STUDENT CAN BE EVALUATED ONLY AFTER HAVING DELIVERED THE REPORTS OF RESULTS ON THE EXPERIMENTAL WORK DONE IN THE LABORATORY MODULE. 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.