Learning objectives
1. Teaching the scientific method for approaching organic chemistry.
2.Providing the basis for the interpretation of the main phenomena occurring in the biological systems and in foods as a result of technological processes and during storage.
3. Showing how the molecular approach form the basis for understanding the structural and functional characteristics of foods (structure, physical-chemical properties and biological activity, sensory properties, etc.).
4. Providing knowledge about the experimental methods used in research and control laboratories.
Course unit content
Covalent bond, the concepts of valence, electronegativity, polarity. Classification and properties of organic solvents. Lewis/Kekulé structures, molecules, hybrid orbitals of carbon. Alkanes: structure, nomenclature, chemical and physical properties, isomerism, conformations. Cycloalkanes and substituted cycloalkanes: stability, isomerism, conformations.
Reactions of alkanes: combustion, halogenation, radical reaction with oxygen. Mechanism of radical reactions. Radicals and their stability.
Stereoisomery. Chirality. Chemical and physical properties of the enantiomers. Racemic mixtures. Diastereoisomers. Stereochemical approach to organic reactions.
Definition and properties of acids and bases. Relationships between structure and acidity. Nucleophiles and electrophiles.
Alkyl halides. Structure and nomenclature. Aliphatic nucleophilic substitution. SN2 mechanism: effect of alkyl group, leaving group, nucleophile and solvent. Stereochemistry of the SN2 reaction. SN1 mechanism: effect of alkyl group, leaving group, nucleophile and solvent. Transpositions. Stereochemistry of the SN1 reaction. Comparison between the two mechanisms.
Alkenes. Structure, physical and chemical properties, nomenclature, cis-trans stereoisomerism, stability. Beta-Elimination. E2 mechanism, stereoelectronic requirements, regioisomers, Saitzev rule. Effect of alkyl group, leaving group, base, solvent and temperature. E2/SN2 competition. E1 mechanism. Comparison E2/E1.
Structure, nomenclature and physical properties of alcohols. Acidity of alcohols. Conversion of alcohols into alkyl halides and dehydration reactions with acid catalysis. Oxidation of primary and secondary alcohols. Formation of ethers via Williamson reaction. Structure, nomenclature and physical properties of ethers. Reactivity of ethers. Structure and preparation of epoxides and their reactivity with acidic and basic catalysis. Structure, nomenclature and physical properties of thiols and thioethers. Acidity and oxidation of thiols, disulfide bond formation.
Reactions of Alkenes: Addition. Hydrogenation. Electrophilic addition of halogen acid, water, halogens, mechanism and regiochemistry. Polymerization of alkenes. Structure, physical and chemical properties, nomenclature and acidity of alkynes.
Definition of resonance. Benzene and aromatic compounds: stability, Huckel definition of aromaticity. Reactivity of aromatic compounds: examples of electrophilic aromatic substitution. Heteroaromatic compounds.
Resonance effects on organic reactions. Resonance of allylic carbocations, conjugated dienes and 1,2 and 1,4 additions, kinetic control and thermodynamic control. Benzylic carbocations. Resonance in the allylic radicals: effects on radical reactions. Benzyl radicals.
Bibliography
Browm, Foote, Iverson, Anslyn. "Chimica Organica". Ed. Edises
McMurry. "Chimica Organica". Ed. Piccin
Teaching methods
Class lectures, class exercises, lab exercitations
Assessment methods and criteria
Written and oral examinations
