Università Roma Tre

Part 1: STRUCTURAL THEORY. ISOMERS AND STEREOISOMERS. RESONANCE AND ELECTRONIC EFFECTS. FUNCTIONAL GROUPS: STRUCTURE, NOMENCLATURE (IUPAC AND COMMON NAMES) AND CHEMICAL-PHYSIC PROPERTIES FOR ALKANES, CYCLOALKANES, ALKENES, ALKYNES, ARENES, HALIDES, ALCOHOLS, THIOLS, ETHERS, SULFIDES, AMINES, ALDEHYDES, KETONES, ACETALS, IMINES, PHENOLS, CARBOXYLIC ACIDS, ESTERS, LACTONES, AMIDES, IMIDES AND NITRILES. HOMO- AND HETERO-AROMATIC COMPOUNDS. MAIN REACTION MECHANISMS: RADICAL SUBSTITUTION AND ADDITION, ELECTROPHILIC ADDITION; POLYMERIZATION; NUCLEOPHILIC SUBSTITUTION (SN1, SN2) AND ELIMINATION (E1, E2) AT SP3 CARBON; AROMATIC ELECTROPHILIC SUBSTITUTION; NUCLEOPHILIC ADDITION AND SUBSTITUTION AT CARBONYL CARBON. SYNTHESIS AND REACTIVITY OF FUNCTIONAL GROUPS IN VIEW OF REACTION MECHANISMS. ENOLATES AND THEIR INTER-, INTRA-MOLECULAR AND CROSS CONDENSATIONS. DI- AND POLY-FUNCTIONAL MOLECULES: ACETACETIC AND MALONIC SYNTHESIS, HYDROXYACIDS, ENONIC SYSTEMS

Part 2: INTRODUCTION TO ORGANIC CHEMISTRY LABORATORY. PURIFICATION AND SEPARATION TECHNIQUES: CRYSTALLIZZATION, EXTRACTION, DISTILLATION AND CHROMATOGRAPHY (ADSORPTION, DISTRIBUTION, IONIC EXCHANGE, AFFINITY); MENTION OF HPLC, GAS-CHROMATOGRAPHY. PRACTICAL EXPERIENCES IN THE LABORATORY: POLARIMETRY, MALEIC TO FUMARIC ACID ISOMERIZATION, SEPARATIONS BY EXTRACTION, NUCLEOPHILIC SUBSTITUTION, TLC AND COLUMN CHROMATOGRAPHY, ESTERIFICATION.

SEYHAN EGE "CHIMICA ORGANICA ESSENZIALE", THIRD ITALIAN EDITION, IDELSON-GNOCCHI, NAPOLI. ADDITIONAL SLIDES CAN BE DOWNLOADED (PASSWORD REQUIRED) FROM WEB SITE: HTTP://HOST.UNIROMA3.IT/CENTRI/CISDIC/INDEX.HTM
SLIDES, PROTOCOLS FOR PRACTICAL CLASS AND QUESTIONNAIRES CAN BE DOWNLOADED (PASSWORD REQUIRED) FROM WEB SITE: HTTP://HOST.UNIROMA3.IT/CENTRI/CISDIC/INDEX.HTM

Part 1: structural theory. isomers and stereoisomers. resonance and electronic effects. functional groups: structure, nomenclature (IUPAC and common names) and chemical-physic properties for alkanes, cycloalkanes, alkenes, alkynes, arenes, halides, alcohols, thiols, ethers, sulfides, amines, aldehydes, ketones, acetals, imines, phenols, carboxylic acids, esters, lactones, amides, imides and nitriles. homo- and hetero-aromatic compounds. main reaction mechanisms: radical substitution and addition, electrophilic addition; polymerization; nucleophilic substitution (SN1, SN2) and elimination (E1, E2) at sp3 carbon; aromatic electrophilic substitution; nucleophilic addition and substitution at carbonyl carbon. synthesis and reactivity of functional groups in view of reaction mechanisms. enolates and their inter-, intra-molecular and cross condensations. di- and poly-functional molecules: acetoacetic and malonic synthesis, hydroxy acids, enonic systems

Part 2: an introduction to organic chemistry laboratory. purification and separation techniques: crystallization, extraction, distillation and chromatography (adsorption, distribution, ionic exchange, affinity); mention of HPLC gas-chromatography. practical experiences in the laboratory: polarimetry, maleic to fumaric acid isomerization, separations by extraction, nucleophilic substitution, TLC and column chromatography, esterification.

T.W. Graham Solomons; Craig B. Fryhle in “Organic Chemistry”, 10th Edition, Wiley.
John McMurry in “Chimica Organica”, Piccin-Nuova Libreria
Bruno Botta in “Chimica Organica” Edi-ermes

Lecture notes and bibliographical references will be provided


The teacher receives Tuesday from 17.00 to 19.00 by appointment via e-mail: tecla.gasperi@uniroma3.it