Learning outcomes of the course unit
To acquire knowledge of the structure and reactivity of organic molecules, with particular attention to molecules of applicative interest. To acquire knowledge on classification 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 and of their consequences in applications and in biological systems.
General Chemistry exam passed
Course contents summary
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 and combustion reactions. Industrially relevant processes.
3-Cycloalkanes. Ring strain, boat and chair conformations of cyclohexane and in substituted cyclohexanes.
4-Stereochemistry. Conformational and configurational isomers; chirality, optical activity, relative and absolute configurations; classification and separation of stereoisomers; role of chirality in biological systems and in technological processes.
5-Alkenes. Cis/trans isomerism. Hydrogenation. Reactivity towards electrophiles and radicals. Examples of polymerization. Dienes: classification. Conjugated dienes: chemical and electronic properties.
4-Alkynes. Structure, nomenclature, and main reactivity.
5-Aromatic compunds. Definition of aromaticity. 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, nucleophilicity. Substitution and elimination reactions on alcohols . Structure and reactivity of ethers, epoxides, thiols and thioethers. Examples of industrial and natural products containing these functional groups.
8-Aldehydes and ketones . 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. Aldol condensation.
9- Introduction 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. Basic hydrolysis. Enolates of carboxylic acid derivatives.
11-Lipids. Classification. Description of the structure and reactions of triglycerides.
11-Amines, amino acids and proteins. Acid-base properties. Structure of peptide and proteins.
Textbook: J. McMurry “Chimica Organica” 7 Edizione. Piccin 2008. Equivalent texts:
P.Y. Bruice “Chimica Organica” EdiSES (2005). 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.
Lectures with computer presentaiton and blackboard.
Tutorials: written exercises concerning fundamental concepts will be proposed, to help the students to practise with notations and tools of Organic Chemistry, through the discussion of cases of increasing difficulty.
Written exam with problem to be solved+ oral examination on theoretical subjects.