LEARNING OUTCOMES

As part of the need to give students a robust foundation in Organic Chemistry, in order to be able to face the subsequent Organic Chemistry II course, the program carried out includes notions of nomenclature of the main organic molecules, notions concerning the chemistry of the main functional groups and systems aromatics, and notions concerning nomenclature and structure of the 20 natural amino acids. An essentially mechanistic approach is followed for the rationalization of the experimental results described.

AIMS AND LEARNING OUTCOMES

The course aims to provide logical and systemic tools, taking care of their learning, to allow all attending students to achieve a good knowledge of structure, physical characteristics, reactivity, mechanistic action, synthesis of the main functional groups of organic chemistry as a basis for all future studies in the sector and their theoretical and applicative insights. The course aims to describe the fundamental principles of Organic Chemistry facilitating their study with the introduction of electronic theories and the continuous application of their concepts, in order to give the subject a certain coherence. Without these assumptions, in fact, Organic Chemistry can appear as a non-homogeneous set of methods and reactions to be learned in a mnemonic way. The main knowledge will concern: - the general aspects and foundations of reactivity - the characteristics of the main functional groups - stereochemistry, that is the three-dimensional aspects that can characterize an organic molecule - the basis for describing the mechanism of a reaction. The main skills (i.e. the ability to apply the knowledge acquired) will be: - identify the way in which a functional group can react - use the acquired knowledge to propose the synthesis of an organic molecule

PREREQUISITES

Passing the preparatory exam in General and Inorganic Chemistry.

TEACHING METHODS

The course includes 3 weekly lectures of 2 hours each during which all the notions concerning the program of the CTF Course are transmitted to the students in detail using slides organized by the teacher himself. The complete slides that cover the entire program of the course are provided to students from the first day of class and are sufficient for an exhaustive preparation. However, supporting texts and exercises are highly recommended. Most of the lessons are held on the blackboard to accustom the student to drawing molecules and reactive patterns. The lessons are also supplemented with exercises and examples on a topic-by-topic basis. The last part of the course (after the Christmas break) is instead dedicated exclusively to exercises and simulations.

SYLLABUS/CONTENT

Spatial organization of organic molecules. Carbon. Structural, optical and conformational isomerism. Fischer projections. Racemic mixtures. Newman projections. Alkanes: radical halogenations and preparations. Alicyclic hydrocarbons: stability of cycloalkanes. Preparations of cyclopropanes. Alkenes: the ethylene double bond. Geometric isomerism. Electrophilic and nucleophilic reagents. Reactions: catalytic hydrogenation; addition of HX, X2, HClO, HBrO, H2SO4, H2O. Markovnikov's rule and carbocations. Isomerization of olefins. Oxymercuriation-demercuriation. Hydroboration-oxidation. HBr's anti-Markovnikov addition. Allyl halogenation. Oxidations. Oxidative cleavages. Preparations. Alkynes: the triple acetylene bond. Acidity of acetylene hydrogen; formation of metal derivatives. Reactions: reductions to alkanes and to cis or trans alkenes; addition of X2, HX, H2O. Preparations. Structure of isolated, conjugated and accumulated dienes. The cumulens. Resonance in conjugated dienes. Aromatic hydrocarbons. Benzene: aromatic electrophilic substitution reactions. Orienting influence of substituents. Mesomeric and inductive effect. Classification of substituents. The arenas: preparations and reactions. Alkyl halides: SN2, SN1, E2, E1 reactions. Reactions with metals. Reduction to alkanes. Preparations. Vinyl halides: electrophilic addition reactions, dehydrohalogenation, reaction with magnesium; inertia towards substitutions. Preparations. Aryl halides: aromatic nucleophilic substitution reactions (addition-elimination, elimination-addition); reaction with magnesium and lithium alkyls. Preparations. Alcohols: hydrogen bonds. Acid-base properties. Formation of salts and ethers. Reactions: oxidation, dehydration, transformation into alkyl halides. Eliminations and replacements. Preparations. Phenols: acid-base properties. Formation of ethers. Kolbe and Raimer-Tiemann reactions. Preparations. Ethers: acid splitting. Basic properties. Trialkyloxonium salts. Williamson synthesis. Preparations. Epoxides: addition of HX catalyzed water, alcohols, ammonia, amines, HCN, Grignard, metal hydrides. Preparations: oxidation of olefins, dehydrohalogenation of halohydrins. Organometallic compounds: reactivity. Preparations of organometals of lithium, magnesium, zinc, cadmium. Grignard: reactions with acids, water, oxygen, halogens, carbon dioxide, carbonyl compounds, esters, acid chlorides, epoxides, disubstituted amides, nitriles. Secondary reactions. Organic cadmium and lithium dialkylcuprates: reactions. Reformatsky. Aldehydes and ketones: the carbon-oxygen bond. Reactions: catalytic reduction; Clemmensen reduction. Oxidation of aldehydes. Nucleophilic addition to the carbonyl. Reductive amination; Wolff-Kishner reduction; Cannizzaro reaction. Acidity of hydrogens in alpha to carbonyl. Enolization. Carbanions-enolanions. Catalyzed alpha halogenation. Haloform reaction. Introduction to aldol condensation. Wittig reaction. Preparations. Oppenauer oxidation and Meerwein-Pondorf-Oppenauer-Verley reduction. Carbeni. Carboxylic acids: acidity; salt formation. Reduction with lithium aluminum hydride. Formation of acyl halides. Hell-Volhard-Zelinsky reaction: reaction equation and products. Acyl derivatives. The acyl function. Nucleophilic acyl substitution. Fischer esterification. Reactions with Grignard and lithium aluminum hydride. Acyl and carboxylated halides, organic cadmium compounds and lithium dialkylcuprates. Reductions of acyl halides. Claisen condensation. Nitrile synthesis, malonic synthesis. Acetoacetic synthesis. Nitriles: catalyzed addition of water and alcohols, reduction to imines and amines, Reactions with Grignard. Acidity of hydrogens in alpha to CN. Alkylation of acetonitrile. Preparations of nitriles. Amines: stereochemistry of nitrogen, acid-base properties. Reactions with: alkali metals, Grignard, acyl halides, anhydrides, alkyl halides, carbonyl compounds, nitrous acid. Amine preparations: Gabriel synthesis, Hofmann, Curtius, Schmidt degradation. Eschweiler-Clarke methylation. Salts of diazonium: structure and stability. Nitrogen replacement reactions with -Cl, -Br, -CN, -I, -F, -OH, -H and copulation. Diazomethane: structure. Reactions with: inorganic, carboxylic acids, mobile hydrogen compounds, acyl chlorides. Arndt-Eistert reaction. Preparation. Introduction to amino acids generic structure and configuration of natural alpha amino acids.

RECOMMENDED READING/BIBLIOGRAPHY

R. T. MORRISON, R. N. BOYD "ORGANIC CHEMISTRY" (Ambrosiana Publishing House) M. LOUBON "ORGANIC CHEMISTRY" (EdiSES) John McMurry, ORGANIC CHEMISTRY, Ed. Piccin Paula Yurkains Bruice, ORGANIC CHEMISTRY, Ed. EdiSES Botta et all, ORGANIC CHEMISTRY, Edi-Ermes Ed Solomons Fryhle, ORGANIC CHEMISTRY, Ed. Zanichelli Brown, ORGANIC CHEMISTRY, Ed. EdiSES Fessenden & Fessenden, ORGANIC CHEMISTRY, Ed. Piccin M.V. D'Auria, O.T. Scafati, A. Zampella, REASONED GUIDE to LEISURE EXERCISES of ORGANIC CHEMISTRY, Ed. Loghia

Any other texts will be communicated to students year by year at the beginning of the course. Texts that the student had available are evaluated by the teacher for their suitability at the beginning of the course.