CHIM/06 - 6 CFU - 1° Semester

Teaching Staff


Learning Objectives

Aim of the course is to acquire the knowledge of the key concepts of the organic chemistry. In particular, the course is aimed:

- to introduce the fundamental knowledge for the study of the basic organic molecules in relation to its structure, reactivity, properties;
- to know the main classes of organic molecules;
- to the view of simple organic molecules in three dimensions with an emphasis to their stereochemical properties.

Furthermore, in reference to the so-called Dublin Descriptors, this course helps to acquire the following skills:

D1 - Knowledge and understanding: The students will have to demonstrate their mastery of basic knowledge about the organic chemistry. In particular, the students must show their ability to
rationalize property-structure correlations of organic molecules
D2 - Ability to apply knowledge: The students will have to show knowledge and understanding of organic reactions required to produce synthetic processes of relatively complex molecules.
D3 - Autonomy of judgment: The students will have to apply their knowledge, understanding and skills. Particularly, the students must show his ability to critical reasoning and their ability to
identify the most appropriate chemical reactions aimed to the synthesis of organic molecules.
D4 - Communication skills: The students must be able to communicate clearly with a correct property of language and terminological rigor their conclusions.
D5- Learning skills: The students will have to develop learning skills that will enable them to continue studying in a self-directed or autonomous way.

Course Structure

Classroom Lectures and Exercises (42 hours)

Detailed Course Content

Introduction to carbon chemistry. Recalling the concepts of atomic orbitals. Electronic configuration of atoms. Representations of Lewis. The octet rule. The chemical bond. Covalent bonds and the Pauling electronegativity scale. Resonance theory. σ and π bonds. Hybrid orbitals sp3, sp2, sp. Intermolecular interactions. Classification of organic compounds and functional groups. General principles of the IUPAC nomenclature for organic compounds. Graphical representation of molecules.

Reactions in organic chemistry. Chemical bonds cleavage. Classification of carbon and hydrogen atoms in organic molecules. Carbocations, carbanions and alkyl radicals: geometry and stability. Reaction mechanisms, use of curly arrows for their representation. Energy diagrams. Recalling the concepts of acid and basic. Acid-basic reactions and redox reactions of organic compounds. Electrophiles and nucleophiles. Reaction classification: substitution, elimination and addition reactions. Regioselectivity, stereoselectivity, stereospecificity aspects of the reactions in organic chemistry.

Alkanes and cycloalkanes. IUPAC nomenclature. Source and importance of alkanes. Physical and chemical properties. Constitutional isomerism and conformational isomerism in alkanes. Cycloalkanes. Geometric isomerism of cycloalkanes. Reactivity: radical substitution and combustion reaction.

Constitutional isomers and stereoisomers. Constitutional isomerism. Stereoisomerism: conformational and configurational isomerism. Chirality. Asymmetric carbon. Enantiomers. Optical activity. Relative configuration and absolute configuration. Naming enantiomers: the R,S system of nomenclature. Three-dimensional representation of enantiomers. Stereoisomers with two or more asymmetric carbon atoms. Diasteroisomers and meso compounds. Biological importance of chirality. Geometric isomerism: cis-trans isomers.

Alkenes. Structure and nomenclature. Geometric isomers of alkenes: cis-trans and E-Z nomenclature. Physical properties. Alkenes in nature. Dienes, trienes and polyenes (hint). Methods of preparation of alkenes. Carbon-carbon double bond reactivity: the electrophilic addition reaction in alkenes. The reaction mechanism. The addition of halogenidric acids and regioselectivity. Markovnikov's rule. The addition of water. The addition of halogens. Cyclic alkenes.

Alkynes. Nomenclature. Triple bond structure. Reactivity. Acidity of a hydrogen bonded to an sp hybridized carbon. The addition reaction in alkynes.

Aromatic compounds. Structure and properties of benzene. Resonance energy and aromaticity concept. Hückel's rule. Nomenclature of mono-, di- and poly-substituted benzene derivatives. Reactivity of the benzene ring: the general mechanism for electrophilic aromatic substitution reactions. Halogenation; nitration; sulfonation; Friedel & Crafts alkylation, Friedel & Crafts acylation. Reaction of substituents on benzene. The effect of substituents on reactivity and orientation.

Alkyl and aryl halides. Structure and nomenclature. Preparation methods. Reactions of alkyl halides. Aliphatic nucleophilic substitution: the SN1 and SN2 mechanisms: role of substrate, leaving group, solvent and nucleophile. The elimination reaction (β-elimination): the mechanisms E1 and E2. The stereochemistry of substitution and elimination reactions. Competition between substitution and elimination reactions.

Alcohols. Structure, nomenclature and classification of alcohols. Physical properties: the hydrogen bond. Preparation methods. Diols and glycols (hints). Alcohol group reactivity. Salt formation; acid and basic properties. Reaction with metals. Formation of alkyl halides: reactions with halogenidric acids (SN2 and SN1). Reaction with SOCl2 and PBr3. Alkenes formation: acid-catalyzed dehydration (E1 and E2). Regioselectivity and stereoselectivity. Oxidation of primary and secondary alcohols. Formation of semi-acetals and acetals. Ethers, epoxides, thiols and sulphides (hints).

Phenols. Acidity of phenols. Phenols in nature. Electrophilic aromatic substitution reactions of Phenols.

Aldehydes and ketones. Structure. Nomenclature. Preparation methods. Chemical and physical properties of the carbonyl group. Reactivity. Nucleophilic addition reactions: addition of alcohols, water, Grignard reagents, HCN. Addition of primary amines: formation of Schiff bases. Oxidation. Reduction of carbonyl compounds. Keto-Enol tautomerism.

Carboxylic acids. Structure and nomenclature. Physical properties. Preparation methods. Acidity. Effect of substituents on acidity in aliphatic acids; salts and soaps formation. Reactions of carboxylic acids. Reduction with LiAlH4: formation of primary alcohols. Decarboxylation. Fischer esterification.

Functional derivatives of carboxylic acids. Acyl halides, esters, anhydrides, amides, nitriles: structure and nomenclature. Reactivity. Nucleophilic acyl substitution reaction. Hydrolysis reactions of carboxylic acid derivatives. Reduction reactions.

Amines. Structure and nomenclature. Physical properties. Basicity. Preparation methods. Reactivity. Amine reactions with nitrous acid.

Carbohydrates. Introduction. Classification and Nomenclature of Carbohydrates. Monosaccharides. Classification of Monosaccharides. The D and L Configurations of Sugars. Fischer’s Proof of the Configuration of Glucose. Cyclic Structures of Monosaccharides. Drawing Cyclic Monosaccharides: The Haworth Projection and Chair Conformations. Disaccharides: Maltose, Sucrose and Lactose. Polysaccharides: Cellulose, Starch and Glycogen.

Amino Acids, Peptides and Proteins. Structure and Sterochemistry of the Amino Acids. Amino Acids in Nature: the α-Amino Acids. Isoelectric Points of the Amino Acids. Peptide Bond. Peptides and Proteins. Levels of Protein Structure.

Lipids (hints). Lipids. Triglycerides and Oils. Soaps and Detergents. Phospholipids and Steroids.

Textbook Information

W.H. Brown – B.L. Iverson – E.V. Anslyn – C.S. Foote - “Chimica Organica”, con modelli molecolari - VI Edizione EdiSES

B. Botta - “Chimica Organica” - Edi-ermes

D. Sica - “Esercizi di Chimica Organica” - EdiSES

W.H. Brown – B.L. Iverson – S.A. Iverson “Guida alla soluzione dei problemi di Chimica Organica” - EdiSES

William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric Anslyn - Organic Chemistry - Cengage Learning (VI Edition)

Thomas N. Sorrell - Solutions to Exercises, Organic Chemistry - Univ Science Books

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