“Organic Chemistry” (A-L) – Natural Science
Lecturer: Dott. Stefano Di Stefano Dipartimento di Chimica, floor I, room 191 tel 0649913057
e-mail stefano.distefano@uniroma1.it
Students target: 60
Level: introductive
Knowledge already acquired: Basic knowledge of general and inorganic chemistry
Credits: 6
Contents
Subject of the Organic Chemistry, diffusion of organic compounds, chemical formulae (brutal, Lewis, Kekulè),
meaning of bond line. Molecular structure, atomic orbitals, ibridization. Reminds on chemical bond, bond length, angle
and energy, dipolar moment. Delocalized bonds and resonance. Brønsted acidity and basicità, Ka and pKa, equilibria,
acids on oxygen (carboxylic acids, phenols and alcohols), and acids on carbon. Lewis acids.
Saturated hydrocarbons: classification, isomerism, names (IUPAC and historical). Alkyl radicals, ramified
hydrocarbons, and cycloalkanes. Structure formulae and projective formulae. Molecular models. Ethane, propane,
butane conformations, Newman formulae. Conformation analysis of cyclohexane. Substituted cyclohexane and
conformational energy of substituents. Trans and cis isomerism. Physical properties: boiling point, solubility, density.
Intermolecular forces: van der Waals, dipolar interactions, hydrogen bonding. Importance and presence of alkanes and
cycloalkanes in nature. Reactivity: radical reactions: alogenation and auto-oxidation. Combustion reaction.
Alkenes and alkynes: names, cis-trans isomerism, E and Z notation, physical properties, importance. Transition state
theory (essential concepts). Mechanisms of organic reactions, energy diagrams, intermediates, reaction rate and reaction
order, catalysts. General mechanism for electrophylic addition to alkenes. Addition of HX: Markownikoff rule and
carbocation stability. Addition of molecular bromine. Hydratation reaction. Catalytic hydrogenation, and alkenes
stability. Oxidation with OsO4.
Optical stereoisomerism: symmetry and chirality, stereocenters, polarimetry and specific rotatory power, enantiomers,
racemic mixture, Fischer projective formulae, relative configuration (D,L), absolute configuration (R, S), Chan-IngoldPrelog priority rules. Prochirality. Compounds with more than one stereocenter: diastereoisomers, mesoforms,
resolution of racemic mixtures (mechanical, chemical, biochemical).
Halogenated compounds: names and importance, nucleophilic substitution to saturated carbon. SN1 and SN2
mechanisms: stereochemistry, steric effects, nucleophile effects, solvent effects. -elimination reactions, E1 and E2
mechanisms Saytzeff rule. Competition between substitutions and eliminations.
Alcohol, phenols, ethers, thiols, sulfides: names, importance and physical properties. Acid properties, Transformation of
alcohols into alcohoxides and bromide or chloride. Dishydratation and oxidation of alcohols. Glicols. Transformation of
alkenes into glicols: sterechemistry.
Arenes: names subtitution in benzene, polycyclic and eterocyclic aromatic compounds. Huckel rule. Electrophylic
aromatic substitution: general mechanism. Halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation.
Activations and orientation concepts.
Amines: names, importance. Basicity of aliphatic and aromatic amines.
Carbonylic compounds, aldheydes and ketones, names, importance, physical properties. Nucleophylic additions.
Acetals and ketals formation. Schiff bases. Reductions and oxidations of carbonylic compounds. Prototropic
tautomerism: enoles and enolates. Aldolic reaction and condensation. Carboxylic acids: names, importance and physical
properties. Conversion to chlorides, bromides, esters, amides, anhydrides. Esters; names importance and physical
properties. Basic and acid hydrolysis: mechanisms.
Lipids and fat acids. Surfactants, Micelles, Phopholipids, lipidic bilayers.
Carbohydrates: classification, and importance. Aldoses and ketoses: Fischer and Haworth formulae, conformational
representations. Anomers, epimers. D-glucose, D-mannose, D-fruttose, D-ribose. Glicosides. Disaccharides: saccharose,
maltose. Polisaccharides.
Ploipeptides and proteins. Natural aminoacids: structure and chimico-physical properties. Isoelectric point. Primari,
secondary, tertiary and quaternari structures of proteins.
Nucleosides and nucleotides, nucleic acids. Importance of the bases. DNA and RNA structures. Genetic code and
biosynthesis of proteins.
Expected output from the students
The student is expected to be prepared on the main general subjects of organic chemistry, from the molecular structures
of the most important organic molecules to their reactivity. Furthermore the student is requested to be competent to
discuss the basic concepì of biochemistry.
CONTENTS
Introduction
Saturated hydrocarbons
Unsaturated hydrocarbons
Stereoisomerism
Aromatic compounds
Monofunctional compounds
Biomolecules
lectures
Practice
lectures
Practice
lectures
Practice
lectures
Practice
lectures
Practice
lectures
Practice
lectures
Lecture hours
Study hours
Total hours
6
2
2
1
4
1
7
2
3
1
10
4
8
51
13
3
4
1
8
2
16
3
6
1
20
4
18
99
19
5
6
2
12
3
23
5
9
2
30
8
16
150
Evaluations
Final evaluation
The evaluation is based on a written examination followed by an oral one..
Suggested Books
W. H. Brown, T. Poon “INTRODUZIONE ALLA CHIMICA ORGANICA” Third edition, EdiSES, Napoli 2005
oppure:
H. Hart, L. E. Craine, D. J. Hart, C. M. Hadad “CHIMICA ORGANICA” Sixth edition, Zanichelli, Bologna 2008
P. Y. Bruice “ELEMENTI DI CHIMICA ORGANICA” First Edition, EdiSES, Napoli 2007
J. McMurry “FONDAMENTI DI CHIMICA ORGANICA” Third edition, Zanichelli, Bologna 2005