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.
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.
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
• 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.
Teaching methods
frontal lectures
Assessment methods and criteria
Written and oral examinations
Other information
Is part of the Course Organic and Bioorganic Chemistry together with a module of practical experiences and bioorganic chemistry
