Learning objectives
To acquire 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
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- Introdiction to the chemistry of carbohydrates. Calssification of carbohydrates. Monosaccharides and their properties. Glycosides. Mutarotation; disaccharides, oligosaccharides and polysaccharides
10- 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-Amines and amino acids. acid-base properties and reactivity.
2-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)Puification of alcohols using distillation. Quantitative analysis of purity by gas-chromatography.
3) Structure and reactivity of carbohydrates. Mutarotation of glucose. Saccharose hydrolysis. Properties and hydrolysis of starch.
4) Synthesis of an ester.
The most common techniques for the separation and identification of organic compounds will be illustrated.
Full programme
http://biotecnologie.unipr.it/cgi-bin/campusnet/corsi.pl/Show?_id=4ecb;sort=DEFAULT;search={docente}%3d~%2f\brcorradini\b%2f;hits=4
Bibliography
Theory
• P.Y. Bruice “Chimica Organica” EdiSES (2005).
• J. McMurry “Chimica Organica” 7 Edizione. Piccin 2008.
• 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
Frontal lectures and Practical laboratory experiences
Assessment methods and criteria
Written and oral examination and written laboratory workbook.
Other information
Integrated course composed of a general part (Organic Chemistry) and a specialized part (Biorganic Chemistry) focused on biomolecules and on practical experiences
