Learning objectives
To acquire knowledge and ability to understand matters of Organic Chemistry in advanced books. Ability to apply knowledge of Organic Chemistry with a professional approach, to design, to discuss and solve problems in the field of Organic Chemistry; to acquire maturity and the necessary skills to undertake studies of higher grade with a good degree of autonomy.
Knowledge of the structure and reactivity of organic molecules, with
particular attention to the biological substances. To acquire knowledge on
classification and nomenclature of the organic compounds by the identification of
their functional groups and , through these, on their reactivity. To learn the concepts
of isomerism, conformation and stereochemistry of organic molecules and of their
consequences in biological systems. To learn the principal concepts characterizing the reactivity of organic compounds in radicalic, electophilic and nucleophilic
reactions. To know the functional groups and properties of some important classes
of biological compounds, such as carbohydrates, triglycerides and amino acids.
To describe the biopolymers of fundamental importance in biological systems:
polisaccharides, peptides, nucleic acids, and their chemical features, their biological
role and fundamentals about chemical synthesis of these molecules.
To acquire experience on the principal laboratory techniques for the purification and
modification of organic compounds.
Prerequisites
General and Inorganic Chemistry
Course unit content
Organic Chemistry
1-The covalent bond and the shape of molecules. Electronic structure-of atoms;
bonds and intermolecular forces; composition, structure and formula of the organic
molecules; structural isomers, resonance. Orbitals of the carbon atom in saturated
and unsaturated compounds.
2-Alkanes. Structure, nomenclature, conformations. Reactivity: formation and
stabilitiy of radicals in halogenation reactions.
3-Cycloalkanes. Ring strain, boat and chair conformations of cyclohexane and in
substituted cyclohexanes.
4-Stereochemistry. Conformational and configurational isomers; chirality, optical
activity, realitve and absolute configurations; classification and separation of
stereoisomers; role of chirality in biological systems and in teechnological
processes.
5-Alkenes. Cis/trans isomerism. Hydrogenation. Reactivity towards electrophiles.
Examples of polymerization. Dienes: classification. Conjugated dienes: chemical
and electronic properties.
4-Alkynes. Structure and nomenclature.
5-Aromatic compunds. Definition of aromaticità. Hückel’s rules. Schematic
description of aromatic electrophilic substitution.
6-Haloalkanes. Structure and reactivity. General scheme for the nomenclature of
functional groups. Substitution and elimination reactions, mono- and bimolecular.
Reaction mechanisms
7-Alcohols. Structure, nomenclature. Chemical properties: acidity, nucelophilicity.
Substitution and elimination reactions on alcohols . Structure and reactivity of
ethers, epoxides, thiols and thioethers. Examples of natural products containing
these functional groups.
8-Aldehydes and kentones . General structure; resonance formulae of the carbonyl
group. Reactions of addition of nucleophilic species (reversible and
irreversible).Oxidation and reduction. Keto-enol tautomerism. Alpha hydrogen
acidity.
9-Carboxylic acids and their derivatives. Structure and nomenclature.. Acidity of
carboxylic acids. Nucleophilic acyl substitution reaction. Order of reactivity.
Structure and reactivity of acyl chlorides, anhydrides, esters, amides. Structure of
triglycerides. Basic hydrolysis.
Bioorganic Chemistry
1-Introduction to the chemistry of carbohydrates. Classification of carbohydrates.
Monosaccharides and their properties. Glycosides. Mutarotation; disaccharides,
oligosaccharides and polysaccharides
2-Amines and amino acids. acid-base properties and reactivity.
3-Peptides and proteins. Chemical structure, physical properties and reactivity.
Introduction to peptide synthesis. Protecting groups.
3-Nucleosides and nucleotides. Structure, physical properties and reactivity.
Introduction to DNA synthesis. Biological and biomedical use of nucleosides and
nucleotides.
Practical part.
Tutorials: written exercises concerning fundamental concepts will be proposed, to
help the students to practise with notations and tools of Organic Chemistry
(structural formulae, resonance structures, conformation and stereochemical
aspects); through the discussion of cases of increasing diffculty. The discussion of
exercises will help to clarify, with examples, the topics exposed in the frontal
module.
Laboratory Practice.
Introduction to the laboratori safety probelms; risks connected with the use of
chemicals and parameters describing hazards and risks.
Practical experiences:
1) Liquid-liquid exctraction of a compound using acid-base aquilibria . Melting point
determination. Qualitative anaysis using thin layer chromatography (TLC).
2)Purification of alcohols using distillation. Quantitative analysis of purity by
gaschromatography.
3)Synthesis of an ester and properties of carbohydrates.
The most common techniques for the separation and identification of organic
compounds will be illustrated.
Full programme
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Bibliography
Theory
• P.Y. Bruice “Chimica Organica-2 Edizione” EdiSES (2nd-Edition 2011).
• J. McMurry “Chimica Organica” 8th Editione. Piccin (2013).
• B. Botta “Chimica Organica” EDI-ERMES (2011)
• W.H. Brown – C.S.Foote – B.L.Iverson E.V. Anslyn “Chimica Organica” IV Edizione EdiSES (2009)
• K. Peter, C. Vollhardt, N.E. Schore “Chimica Organica” 3 Edizione. Zanichelli (2005).
Copies of the lectures available at the course web site.
Laboratory Practice
W.H. Brown, B. L. Iverson, S. A. Iverson: “Guida alla soluzione dei problemi di
Chimica Organica” Edi Ses.
R.M. Roberts, J.C. Gilbert, S.F. Martin : " Chimica Organica Sperimentale"
Zanichelli Editore .
Copies of the lectures available at the course web site.
Teaching methods
Lectures, tutorials and laboratory practise. During the lectures the principles of organic chemistry nomenclature, physical and chemical properties and reactivity of the major classes of organic molecules and biological macromolecules will be addressed. In the tutorials exercises concerning the structure and reactivity of organic molecules and the related problems of understanding will be presented in an interactive manner and discussed with the students. The part of the practical training is preceded by an explanation in the classroom of the risks and protective measures to be used in the laboratory and by the detailed explanation of the procedures of each experience. The experiences consist of laboratory work in small groups (2-3 people) under the supervision of the teacher and experienced staff, followed by a re-elaboration by the student in a written report.
Assessment methods and criteria
L’esame consiste in una prova scritta, e in una prova orale previa consegna delle relazioni di laboratorio
Le conoscenze richieste per il superamento dell'esame sono:
Capacità
Dimostrazione di conoscenze e capacità di comprensione caratterizzato dall’uso di libri di testo avanzati di Chimica Organica. Capacità di applicare le conoscenze di Chimica Organica con un approccio professionale, di ideare, sostenere argomentazioni e risolvere problemi nel campo della Chimica Organica; acquisire la maturità e le conoscenze necessarie per intraprendere studi successivi con un buon grado di autonomia
Competenze
Dimostrazione delle conoscenza della struttura e della reattività di molecole organiche, con particolare riferimento ai composti biologici. Conoscenza nella classificazione e della nomenclatura dei composti organici mediante l’individuazione dei gruppi funzionali che li caratterizzano e, tramite questi, nella descrizione della reattività. Conoscenza dei concetti di isomeria, conformazione e stereochimica delle molecole organiche e delle conseguenze di queste nei sistemi biologici. Conoscenze riguardo ai principali concetti che governano la reattività dei composti organici in reazioni di tipo radicalico, elettrofilo o nucleofilo. Conoscenza dei gruppi funzionali e le proprietà di alcune importanti classi di molecole biologiche quali i carboidrati, i trigliceridi e gli ammino acidi. Dimostrare di aver compreso e rielaborato le principali tecniche di laboratorio di purificazione e modificazione di composti organici utilizzate durante le esperienze pratiche.
L'esame scritto consiste in 6 esercizi di reattività di composti organici da risolevere . Si intende superato se 4/6 domande sono svolte correttamente o, in alternativa, se almeno il 60% dei contenuti espressi complessivamente sono corretti e esaustivi.
L'esame orale consiste nella discussione del quaderno di laboratorio e un approfondimento della parte teorica, in particolare delle parti non comprese nell’esame scritto.
Other information
Contains a part of practical laboratory experiences
