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ORGANIC AND INORGANIC CHEMISTRY 2
(obiettivi)
The course aims to provide a correct knowledge of the fundamental principles of organic chemistry, proposing the contents into two distinct phases that are closely and logically linked. In the first phase the teaching is addressed to provide basic knowledge about classification and nomenclature of organic compounds, about the symbolism used to represent both structures and reactions, as well as over the chemical-physics, acid-base, nucleophilic-electrophilic properties of the considered compounds. In the second phase the teaching is instead focused on the description of the different reactivity involved by different classes of compounds, rationalizing the study through the analysis of the relevant mechanisms. In the context of the described methodology the objectives to be achieved are: 1) attainment of a suitable degree of specialized knowledge, understood as the ability to invoke theories, rules, nomenclature etc.; 2) capacity to properly interpret and process the reaction schemes and propose alternatives to the encountered syntheses; 3) establish connections between different studied subjects.
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BOTTA BRUNO
( programma)
Organic Chemistry
Structure and properties
Carbon compounds, Lewis structural formulas, types of bonds, functional groups, formal charge
stereoisomer characteristics, identifies configuration of double bond cis (Z) /trans (E) identifies configuration of stereocenters (R)/(S), identifies rotation under plane-polarized light to determine whether molecule is (+) or (-), need to do laboratory tests where the molecule is put in plane-polarized light bonding and molecular structure atomic orbitals, covalent bond formation—molecular orbital (MO) method, hybridization of atomic orbitals, electronegativity and polarity, oxidation number, intermolecular forces, solvents, resonance and delocalized π electrons.
Chemical reactivity and organic reactions.
Reaction mechanism, carbon-containing intermediates, types of organic reactions, electrophilic and nucleophilic reagents, thermodynamics bond-dissociation energies, chemical equilibrium rates of reactions, transition-state theory and enthalpy diagrams, brönsted acids and bases basicity (acidity) and structure, Lewis acids and bases.
Alkanes and cyclic hydrocarbons
Definition, nomenclature of alkanes, preparation of alkanes, chemical properties of alkanes.
Nomenclature and structure, geometric isomerism and chirality, conformations of cycloalkanes and chemical properties.
Stereochemistry
Stereoisomerism, optical isomerism, relative and absolute configuration, molecules with more than one chiral centre, synthesis and optical activity.
Alkenes
Nomenclature and structure, geometric (cis-trans) isomerism, preparation of alkenes, chemical properties of alkenes, substitution reactions at the allylic position, summary of alkene chemistry
Alkyl halides
Introduction, synthesis of alkyl halides and chemical properties.
Alkynes and dienes
Alkynes, chemical properties of acetylenes, alkadienes, MO theory and delocalized π systems. Addition reactions of conjugated dienes, polymerization of dienes, cycloaddition.
Benzene and polynuclear aromatic compounds
Introduction, aromaticity and Hückel's rule, polynuclear aromatic compounds, nomenclature chemical reactions.
Alcohols and thiols
Alcohols, nomenclature and H-bonding, preparation and chemical properties. Thiols, nomenclature and chemical properties.
Ethers, epoxides, glycols, and thioethers
Ethers, introduction and nomenclature, preparation, chemical properties. Cyclic ethers. Epoxides, introduction, nomenclature, chemical properties and synthesis. Glycols, nomenclature and chemical properties. Preparation of 1,2-glycols, unique reactions of glycols.
Thioethers, introduction, nomenclature and chemical properties.
Carbonyl compounds: aldehydes and ketones
Introduction, nomenclature, preparation, and chemical properties. Oxidation and reduction of the carbonyl group.
Carboxylic acids and their derivatives
Introduction, nomenclature, preparation of carboxylic acids and carboxylic acid derivatives. Chemical properties of carboxylic acids and carboxylic acid derivatives.
Amines
Nomenclature and physical properties, preparation, chemical properties, reactions of quaternary ammonium salts, ring reactions of aromatic amines, spectral properties, reactions of aryl diazonium salts, summary of amine chemistry
Phenolic compounds
Introduction, Preparation, chemical properties, analytical detection of phenols, summary of phenolic chemistry, summary of phenolic ethers and esters
Aromatic heterocyclic compounds
Five-membered aromatic heterocycles with one heteroatom, six-membered, heterocycles with one heteroatom, compounds with two heteroatoms
Carbohydrates and nucleic acids
Introduction, classification of carbohydrates, the D and L notation, the configuration of aldoses and ketoses. The reactions of monosaccharides in basic solutions. The oxidation-reduction reactions of monosaccharides . lenghtening the chain: the kiliani-fisher synthesis. Shortening the chain: the Ruff degradation. chemical properties of monosaccharides, evidence for hemiacetal formations as exemplified with glucose, stereochemistry and structure proof , disaccharides
Amino acids, peptides, proteins
Introduction, preparation of α-amino acids, chemical properties of amino acids, peptides
Reactivity and Reactions
Radicals
Radical stability. The reactivity-selectivity principle. The chlorination and bromination of alkanes.
Radical addition to alkenes. The sterochemistry of radical substitution and radical addition reactions.
Substitution and elimination reactions
Mechanism and factors that affect reactions SN2. Mechanism and factors that affect reactions SN1.
The stereochemistry of SN2 and SN1 reactions. Competition between SN2 and SN1. The E1 and E2 reactions. Competition between E1 and E2 reactions, and between SN2/E2and SN1/E1 reactions.
Reactions of benzene and of substituted benzenes
The general mechanism of electrophilic aromatic substitution reactions. Halogenation, nitration, sulfonation, Friedel-Crafts acylation and alkylation. The effect of substituents on reactivity and on orientation. Nucleophilic aromatic substitution: addition-elimination mechanism and elimination-addition mechanism.
Carbonyl compounds: reaction of carboxylic acids and carboxylic acid derivatives
General mechanism for nucleophilic addition-elimination reactions. Reactions of acyl halides, acid anhydrides, esters. Acid and basic catalyzed hydrolyses of esters, amides and nitriles.
Carbonyl compounds: reactions of aldehydes, ketones and α,β-unsaturated carbonyl compounds
Reactions of carbonyl compounds with: Grignard reagents, acetylide ions, hydride ions, hydrogen cyanide, amines and amines derivatives, water, alcohols, sulphur nucleophiles. The Wittig reaction. Nucleophilic addition to α,β-unsaturated aldehydes and ketones. α,β-unsaturated carboxylic acid derivatives.
Carbonyl compounds: reactions at the α-carbon
Keto-enol tautomerism. How enolate ions and enols react. Alkylating the α-carbon of carbonyl compounds. Alkylation of the α-carbon using an enamine intermediate. The Michael reaction. Aldol condensation and Claisen condensation. The Robinson annulation.
 Testi:
Graham Solomons, Craig Fryhle: Organic Chemistry Ed. Wiley
Paula Bruice: Organic Chemistry Ed Pearson Chimica Organica: Bruno Botta Ed. Edi-Ermes
(Date degli appelli d'esame)
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6
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CHIM/06
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48
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Attività formative di base
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