Academic Year 2021/2022 - 1° Year
Teaching Staff: Nunzio Cardullo
Credit Value: 6
Scientific field: CHIM/06 - Organic chemistry
Course Language: Italian
Taught classes: 28 hours
Exercise: 28 hours
Term / Semester:

Learning Objectives

The course aims to provide the student with the basic knowledge about the main classes of organic molecules, including biomolecules and organic molecules found in food; with particular attention to the physico- and chemical properties for each class of organic compounds.
At the end of the course the student will acquire the following skills:
- know the IUPAC nomenclature rules for the correct attribution of the name of an organic compound given its structure, and vice versa;
- ability to represent the main classes of organic molecules through structural formulas;
- know and distinguish between the possible isomers associated with a given chemical formula;
- recognize the main functional groups of organic molecules and know the chemical-physical properties associated with them;
- ability to identify a nucleophilic or electrophilic species in common organic chemistry reactions;
- know the mechanisms of the main organic chemistry reactions.

Course Structure

The teaching is divided into 28 hours of lectures and 28 hours of classroom exercises; the latter will focus on all the topics of the course, with particular reference to the chemical properties (reactivity) of the functional groups examined.
Some changes may be introduced with respect to what was previously stated if teaching move from face-to face lectures to mixed or remote way, in order to comply with the program envisaged and reported in the syllabus.

Detailed Course Content

1.Introduction to organic chemistry. Electronic configuration of the carbon atom. The octet rule. Formation of covalent bonds. Polar and apolar covalent bonds. Hybrid orbitals. Molecular orbitals,
structure of sigma and pi bonds, representation of organic structures, the concept of resonance. Non-covalent interactions. Hydrogen bonds. Physical structure and properties. Classification of organic compounds based on functional groups. 2. Reactions in organic chemistry. Homolytic and heterolytic cleavage of a bond. Carbocations, carbanions and radicals. Acids and bases according to Brønsted-Lowry. Acid dissociation constant and pKa values. Factors affecting acidity: electronegativity, atom size, hybridization, resonance. Acids and bases according to Lewis. Redox reactions in organic chemistry. Concept of nucleophile and electrophile. Classification of reactions as substitution, addition and elimination. Exercises. 3. Alkanes and cycloalkanes. Classification of hydrocarbons. IUPAC nomenclature. Branched alkanes. Cycloalkanes. Alkanes’ and cycloalkanes’ conformations. Ring tension and stereoisomerism of cycloalkanes. Physical properties. Alkanes and foods. Chemical properties: combustion and radical substitution reaction. Exercises. 4. Stereochemistry. Chirality. Asymmetric carbon and stereogenic center. Enantiomers and diastereomers. Absolute configuration R, S. 3D representation methods of molecules, Fisher projections. Optical activity. Stereoisomers with two or more asymmetric C atoms. Physical properties of enantiomers and diastereomers. Racemes and their resolution. Exercises. 5. Alkenes. IUPAC nomenclature. Structure: bond lengths. Cis-trans geometry in alkenes. E, Z nomenclature. Physical properties. Alkenes present in food. Isoprenoids. Chemical properties: electrophilic addition reaction to the double bond. Addition of halogenhydric acids. Stability of carbocations. Regioselectivity: Markovnikov's rule. Addition of halogens. Addition of H2O. Formation of halohydrins. Catalytic hydrogenation. Exercises. 6. Alkynes. IUPAC nomenclature. Structure: bond lengths. Physical properties. Electrophilic addition of halogen and halogen acids. Addition of water. Hydrogenation. Lindlar catalyst. Acidity of terminal alkynes: acetylides. Exercises. 7. Alkyl Halides. IUPAC nomenclature. Structure. Physical properties. Chemical properties. SN2 Bimolecular Nucleophilic Substitution Reaction. Factors influencing SN2 reactions: leaving group, nucleophile, protic and aprotic solvents. Nucleophilic monomolecular substitution SN1. Mechanism of SN1. Stability of carbocations and order of reactivity in SN1. Factors influencing SN1 reactions. Allyl halides. E2 bimolecular elimination reaction. Zaitsev's rule. Monomolecular elimination E1. Exercises. 8. Alcohols and ethers. IUPAC nomenclature. Structure. Physical properties. Hydrogen bonds. Alcohols present in food. Chemical properties. Acidity and basicity. Reaction with metals. Formation of alkyl halides: reactions with halogenhydric acids and with halogenating agents; reactions of SN1 and SN2. Acid-catalyzed dehydration; reactions of E1 and E2. Oxidation of alcohols. Hint of ethers, epoxides, thiols and sulphides. Exercises. 9. Aldehydes and ketones. Nomenclature of aldehydes and ketones. Structure of carbonyl compounds: the CO bond: molecular orbitals and resonance. Physical properties. Chemical properties. Nucleophilic addition reaction to the carbonyl. Reaction with Grignard reagents. Reaction with acetylides. Reaction with alcohols: formation of hemiacetals and acetals. Cyclic hemiacetals: carbohydrates. Formation of imines (Schiff bases) and enamines. Oxidation of aldehydes and ketones. Reduction to alcohols. Exercises.
10. Carboxylic acids and derivatives. Nomenclature. Common names of carboxylic acids of natural origin; fatty acids. Nomenclature of acid derivatives: acyl halides, anhydrides, esters, amides, nitriles. Structure of acids and derivatives. Physical properties. Chemical properties: nucleophilic acyl substitution reaction. Reactivity scale of carboxylic acids and derivatives. Fisher's esterification. Reduction of with LiAlH4. Hint on the reactions of carboxylic acid derivatives. Exercises. 11. Aromatic hydrocarbons. Structure and properties of benzene. Aromaticity and Huckel's Rule. Nomenclature of benzene derivatives. Aromatic compounds present in food. Chemical properties: aromatic electrophilic substitution reaction. Halogenation, sulfonation, nitration, Friedel-Crafts reactions. Activating and deactivating groups. Phenols. Physical characteristics. Acidity of phenols and comparison with alcohols. Exercises. 12. Amines. Aliphatic and aromatic amines. Nomenclature and structure. Physical properties: hydrogen bond. Amines present in food. Basicity. Outline of the chemical properties of aliphatic amines. Exercises. 13. Carbohydrates. Classification and nomenclature. Configuration of monosaccharides. Fischer projections. Series D and L. Cyclic forms. The glucose molecule. Outline of the most common disaccharides and polysaccharides present in food. 14. Amino acids and protein. Structure of amino acids. Natural amino acids. Isoelectric point. The peptide bond. Primary, secondary, tertiary and quaternary structure of proteins. 15. Lipids. Lipid structure and properties. Fats and oils. The soap. Membrane phospholipids. The waxes.

Textbook Information

1. W.H.Brown, B.L. Iverson, E.V.Anslyn. C.S.Foote: Chimica Organica, EdiSEs.
2. J. McMurry: Chimica Organica, Zanichelli.
3. F. Nicotra, L. Cipolla: Eserciziario di Chimica Organica, EdiSES.

Lectures material (slides, handouts, exercises, bibliography), in addition to the recommended text, will be available through the STUDIUM platform.