Learning outcomes of the course unit
The course has the objective to teach the student the scientific method for approaching organic chemistry, providing the background for the interpretation of the main phenomena happening in biological systems and in foods In this way a molecular vision will be provided to the student, which will constitute the background for understanding the functional and structural characteristics of foods (correlation structure-physical/chemical properties-biological activity, sensory properties, etc.). At the same time, the exercitations in the lab will provide applicative knowledge on the chemical properties of the organic compounds and on the experimental methodologies used in the research and control laboratories, developing the student ability to apply what taught in classroom. The course will help the student to develop the ability to use, from the theoretical and practical point of view, the learned concepts, using them to solve problems related to the chemical transformations at the molecular level and developing the autonomy of judgment and the critical reasoning. Moreover, through the written and oral exposition during the various stages of the exam, the student ability to effectively communicate the acquired knowledge will be exercised.
The course has to be attended after the course of General Chemistry. Only the stdent having completed and registered General Chemistry will be allowed to do the various stages of the exam of Organic Chemistry.
Course contents summary
- Covalent bond and molecular structure
- Acids and bases
- Alkanes and cycloalkanes
- Alkenes and alkines
- REactions of alkenes and alkines
- Chirality and molecular asymmetry
- Alcohols, ethers and thiols
- Benzene and its derivatives
- Aldheydes and ketones
- Carboxylic acids
- Functional derivatives of carboxylic acids
- Enolate anions
- Amino acids and proteins
- Covalent bond and structure of molecules. Organic compounds. Carbon hybridization, common functional groups, classes of organic molecules.
Acids and bases, structure acidity relationship. Bronsted and Lewis acidity and basicity.
- Alkanes: structure, nomenclature, physical and chemical properties, conformations. Cycloalkanes. Reactivity of the CH bond: combustion, autooxidation, halogenation. Carbon radicals. Number of oxidation of organic compounds.
- Alkenes, structure, nomenclature and properties. Isomerism. Hydrogenation of the double bond. Mechanism of electrophilic addition to double bonds: addition of halogenhydric acid, water, halogens. Polymerization, synthetic and natural polymers. Dienes, the effects of conjugation. Alkynes.
- Chirality. Relative and absolute configuration. Diastereoisomers, enantiomers. Stereochemistry of cycles. Importance of stereochemistry in living systems and food.
Haloalkanes. Reactivity of haloalkanes. Electrophilicity and nucleophilicity. Nucleophilic substitution reactions, Sn2 and Sn1 and Elimination reactions, E1 and E2.
- Alcohols: structure, nomenclature, physical and chemical properties, reactivity. Nucleophilic substitution reactions, Sn1 and Sn2 mechanisms. Carbocations. Elimination reactions, E1 and E2 mechanisms. Ethers. Thiols. Sulphides.
- Aromatic compounds, aromaticity and Hückel rules. Heteroaromatic. Phenols and aromatic amines. Electrophilic aromatic substitution reaction.
Amines. Basicity of the amines, amines as nucleophiles. Aromatic amines.
- Aldehydes and ketones: structure, nomenclature and physico-chemical properties. Mechanism of nucleophilic addition. Addition of water. Addition of alcohols: formation of hemiacetals and acetals. Addition of amines: formation of imines. Oxidation of aldehydes.
- Carboxylic acids: structure, nomenclature, acid properties.
- Derivatives of carboxylic acids. Mechanism of nucleophilic acyl substitution. Esters: nomenclature and properties. Basic and acid hydrolysis. Fisher esterification. Amides: nomenclature and properties. Basic and acid hydrolysis of amides- Lipids. Structure and properties of fatty acids and triglycerides. Triglycerides formed by saturated and unsaturated fatty acids. Saponification, autooxidation, hydrogenation. Oxidative and hydrolytic rancidity.
-Enols. Keto-enolic tautomeris. Reactions of formation of carbon-carbon bonds. Aldolic and Claisen condensation. Condensations in a biological environment.
- Carbohydrates. Saccharide structure, conformation in solution, mutarotation. Glucose, fructose, galactose. Glycosides. Oxidation of sugars, reducing sugars. Reactions with amines, the Maillard reaction. Thermal decomposition: caramelization reaction. Disaccharides: maltose, cellobiose, lactose, sucrose. Hydrolysis of disaccharides, inverted sugar. Polysaccharides: amylose, amylopectin, starch, glycogen and cellulose.
- Amino acids: acid-base properties, isoelectric point. Peptides and proteins: structure, properties and classification. Protein in food.
Brown, Poon: Introduzione alla Chimica Organica (EDISES)
The course is divided in lecturing hours about the theory, classroom exercises to apply the theory to practical problems and laboratory exercitations (in groups of two-three students) to make the student familiar with the chemical properties of the organic compounds.
Assessment methods and criteria
The exam is constituted by a written test on the first part of the course followed by a written test on the second part of the course. The second written test can be done only after having passed the first written test. Every written test will be based on open questions (from 4 to 6) covering all the aspects of the program. Every question will yield the same number of points independently by the difficulty. The sum of all points will give the maximum mark of 30/30. The passing level is 18/30. Then an oral examination will follow, which can be done only after having passed both written tests and having handed the laboratory notebook. The average of the written and oral tests will be the final mark for this exam.
The educational material is provided to students at the beginning of the course. The teacher remains with the students for clarification and discussion at the end of the lesson and is available to provide further explanation, by appointment.