Learning outcomes of the course unit
1. Teaching to the student the scientific method for studying organic chemistry.
2. Giving the bases for the interpretation of the main phenomena happening in the biological systems and in food as a consequence of the technological processes and during the conservation.
3. Showing that a knowledge at the molecular level constitutes the base for the understanding the structural and functiona characteristics of foods (correlation structrue - physico-chemical properties and biological activity, organoleptical proeprties, etc).
4. Supplying knowledge on the experimental procedures used in control and research laboratories.
Inorganic and General Chemistry must be passed before Organic Chemistry.
Course contents summary
Covalent bond, valence, electronegativity, polarity, Lewis structures of the molecules, hybrid obitals of carbon.
Alkanes. Structure, nomenclature, physico-chemical properties, isomerism, conformations. Cycloalkanes and substituted cycloalkanes: stability, isomerism, conformations. Reactions of alkanes: combustion, halogenation, radicalic reaction with oxygen. Mechanism of the halogenation reaction. Radicals and their stability.
Stereoisomerism. Chirality. Physico-chemical properties of enantiomers. Racemic mixtures. Diastereoisomer. Sterochemistry of the radical halogenation reactions.
Alkenes and alkynes. Structure, physico-chemical properties, nomenclature, cis-trans isomerism, stability of alkenes. Reactions of alkenes: additions, hydrogenation. Electrophilic addition of halogenidric acids, water, halogens, mechanisms and regiochemistry. Carbocations and their transposition. Conjugated dienes and 1,2 and 1,4 addition, resonance of the allyl carbocation, kinetic control and thermodynamic control. Polymerization of alkenes. Radicalic halogenation of allyl carbons: the allyl radical. Structrue, physico-chemical properties, nomenclature and acidity of alkynes.
Acidity and Basicity. The concept of acidity according to Bronsted-Lowry, structure-acidity relationship, Lewis acids and Lewis bases.
Benzene and aromatic compounds: stability, definition of aromaticitiy according to Huckel. Benzylic carbocations and radicals. Reactivity of aromatic compounds: examples of electrophilic aromatic substitution. Heteroaromatic compounds.
Alkyl halides. Structure and nomenclature. Aliphatic nucleophilic substitution. Nucleophiles and bases. SN2 mechanism: effect of the alkylic group, leaving group, nucleophile and solvent. Classification and properties of the organic solvents. Stereochemistry of SN2 reaction. SN1 mechanism: effect of the alkylic group, leaving group, nucleophile and solvent. Transpositions. Stereochemistry of SN1 reaction. Comparison between the two mechanisms. Beta-elimination. E2 mechanism, stereoelectronic requirements and regioisomerism, Saitzev rule. Effect of the alkylic group, leaving group, nucleophile, solvent and temperature. Competition E2/SN2. E1 mechanism. Comparison E2/E1.
Alcohols, thiols, ethers, epoxides. Structure, nomenclature and physical properties of alcohols. Acidity of alcohols. Conversion of alcohols in alkyl halides and dehydration reaction with acid catalysis. Oxidation of primary and secondary alcohols. Formation of ethers via Williamson reaction. Structure, nomenclature and physical properties of thiols. Acidity of thiols and oxidation reactions. Structure, nomenclature and physical properties of ethers. Synthesis and reactivity of ethers. Structure and preparation of epoxides and their reactivity with basic and acid catalysis.
Risk factors and safety rules n the chemical laboratories
Laboratory experiences linked to the first module of Organic Chemistry: 1) Miscibility of food fats in various solvents and their reactivity with bromine; 2) Extraction of caffein from tea leaves and identification by determination of the melting point; 3) Purification of benzyl alcohol and methanol by distillation and analysis by GC.
- BROWN, FOOTE. Chimica Organica (Edises).
- MC MURRY. Chimica Organica (Zanichelli).
- VOLLHARDT, SCHORE. Chimica Organica (Zanichelli).
- BRUICE. Chimica Organica (Edises).
- MORRISON, BOYD. Chimica Organica (Ambrosiana).
Written exercises: during the course written exercises on the subjects will be done. Laboratory experiences: during the course various laboratory experiences will be done. For the admission to tha oral examination at least 80% of the experiences are to be attended, and the delivery of the laboratory notebook in occasion of the second written test is compulsory.
The examination of the Integrated Course of Organic Chemistry is intended as one, made up of the following parts: written verification on the arguments of the module of Organic Chemistry I (which can already be done during the suspension week); written verification on the arguments of the module of Organic Chemistry II; oral examination on the arguments of both modules and on the laboratory exoperiences.