Università Roma Tre

Lecture (7CFU): Hybridization of carbon. Functional groups: structure, nomenclature (IUPAC and use) and chemical-physical properties of alkanes, cycloalkanes, alkenes, alkynes, arenes, halides, alcohols, thiols, ethers, sulphides, amines, aldehydes, ketones, imines, phenols, carboxylic acids, esters, lactones, amides, imides and nitriles.
Stereochemistry: isomers and stereoisomers. Inductive and Resonance effects.
The main reaction mechanisms: electrophilic addition to alkenes, dienes and alkynes. Polymerizations. Electrophilic aromatic substitution on benzene and heteroatoms present in biological molecules. Addition to carbonyls and nucleophilic substitution of acyls. Enolates and their condensations. Bi- and polyfunctional molecules: hydroxy acids, enonic systems, ketoacids. Physico-chemical properties of amino acids (structures and isoelectric point). Carbohydrates (classification, hemiacetal structures, glucosides, polysaccharides).
Nucleophilic substitution (SN1, SN2) and elimination (E1 and E 2) at sp3 carbon. Acetacetic and malonic synthesis. Redox reactions on organic compounds. Radical reactions of hydrocarbons (combustion and radical oxidation) using model reaction (halogenation).
Laboratory experiences (2 CFU): Introduction to organic laboratory precedures. Purification tecnique: crystallization, extraction, distillation and chromatography (adsorption, partitioning, ion exchange, affinity); short references on TLC and gas chromatography. Practical experiences in the laboratory: polarimetry, maleic acid/fumaric acid isomerization, separations by extraction, TLC and column chromatography, esterification.

W. H. Brown, B.L. Iverson, E.V. Anslyn, C.S. Foote Organic Chemistry
J. Mc Murry Chimica Organica Ed. Piccin
pdf notes of lessons are available to students on Moodle

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 the 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