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Organic Chemistry (9 CFU) (Canale 1); Program 2024-2025 Introduction to Organic Chemistry: electronic structure of atoms; Lewis bond model; electronegativity; dipole moment of bonds and molecules. Covalent bonding according to the valence bond model: hybridization of atomic orbitals. Formal charge. Resonance. Intermolecular interactions (dipole-dipole interactions, hydrogen bonding, van der Waals forces); polarizability; solubility and physical properties of organic compounds. Acid-base properties: acidity and basicity according to Brønsted-Lowry (Ka and pKa) and according to Lewis. Alkanes. Structural isomers. Molecular models. Perspective and projective formulas. Alkyl groups. Nomenclature. Physical properties. Conformation of alkanes (Newman and sawhorse representations). Cycloalkanes. Nomenclature. Physical properties. Cis-trans isomers. Ring tension. Conformation of cycloalkanes and substituted cycloalkanes. Chirality. Chiral and achiral molecules. Stereocenter (definition). Stereoisomers and Enantiomers. Absolute configuration R/S. Molecules with more than one stereocenters: diastereoisomers and meso compounds. Fischer projections. Properties of stereoisomers. Optically active compounds (observed and specific rotation). Alkenes. Structure and nomenclature. Geometric isomers (cis/trans and E/Z notations). Alkene reactions. Electrophilic additions to double bonds: hydrogen halide additions. Relative stability of carbocations. Rearrangement of carbocations. Hydration reaction of alkenes: acid-catalyzed process. Acid-catalyzed addition of alcohols to alkenes; chlorine and bromine addition to alkenes: halonium ion. Alkene oxidations: glycol formations, epoxidation, ozonolysis. Alkene reductions. Heat of hydrogenation and alkene stability. Regioselectivity and stereoselectivity in addition reactions to alkenes. Alkynes. Structure and nomenclature. Reactivity of alkynes. Addition of H 2 , X 2 , HX and hydration. Acidity of alkynes. Alkylation of acetylide anions. Alkyl halides. Structure and nomenclature. Preparation: halogenation of alkanes, addition of X 2 and HX to alkenes, allyl bromination, formation from alcohols. Aliphatic nucleophilic substitution. SN2 and SN1 mechanisms: stereochemistry and kinetic evidence. Factors affecting the rate of SN2 and SN1 processes: structure of nucleophile, RX, leaving group, and solvent effect. Examples of SN2 and SN1 processes. Beta-elimination reactions. Zaitzev's rule, E2 and E1 mechanism. E2 and E1 comparison. Stereochemistry of E2. Alcohols. Structure, nomenclature and physical properties. Acid-base reactions. Preparation of alcohols from alkenes and alkyl halides. Reactions of alcohols: conversion to alkyl halides and tosylates. Reactions of alcohols: acid-catalyzed dehydration. Ethers. Structure, nomenclature and physical properties. Preparation of ethers: Williamson synthesis. Reactions of ethers: cleavage with acids. Epoxides. Structure, nomenclature and their reactivity in acid- or base-catalyzed processes. Benzene and benzene derivatives. Nomenclature. Resonance energy and aromaticity. Mono- and polysubstituted derivatives. Polycyclic and heterocyclic aromatic compounds. Electrophilic aromatic substitution: halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation reactions. Substituent effects (activation/deactivation and directing effects in electrophilic aromatic substitution processes on substituted benzene rings). Oxydation of alkylbenzenes. Ketones and aldehydes. Nomenclature. Structural characteristics of the carbonyl group. Preparation of aldehydes and ketones. Nucleophilic addition to carbonyl carbon: addition of HCN, alcohols, amines, Grignard reagents. Oxidation and reduction of aldehydes and ketones. Carboxylic acids. Structure and nomenclature. Physical properties. Acidity and effect of substituents. Preparation of carboxylic acids. Reduction of carboxylic acids. Nitriles. Nomenclature. Hydrolysis of nitriles. Derivatives of carboxylic acids. Structure and nomenclature. Conversion of carboxylic acids to acyl chlorides, anhydrides, esters, amides and alcohols. Acyl nucleophilic substitution. Reactions of acyl halides, anhydrides, esters and amides. Enolate anions. Keto-enol tautomeria. Racemization in alpha to carbonyl. Halogenation in alpha position. Acidity of hydrogens in alpha to a carbonyl. Formation of enolates. Alkylation of enolates. Malonic synthesis. Acetoacetic synthesis. Aldolic condensation: symmetrical, cross-linked and intramolecular aldolic reactions. Amines. Classification of amines. Nomenclature. Basicity of amines. Structure-basicity relationship in aliphatic, aromatic and aromatic heterocyclic amines. Preparation of amines. Reactions of amines. Pyridine, pyrrole, imidazole. Carbohydrates. Classification. D- and L-monosaccharides: Fischer projections. Hemiacetal cyclic structure: Haworth formulas and chair conformations. Epimers and anomers. Mutarotation. D- Glucose, D-fructose, D-ribose, D-mannose, D-galactose. Monosaccharide reactions: glycoside formation, reduction and oxidation. Disaccharides: maltose, cellobiose, lactose, sucrose. Polysaccharides: starch, glycogen and cellulose. Amino acids. Classification. alpha-natural amino acids. Acid-base properties. Isoelectric point. Synthesis of amino acids. Polypeptides and proteins: primary, secondary (alpha-helix and structure beta sheet), tertiary and quaternary structure. Chemical synthesis of polypeptides: protecting and activating groups. Hints on solid-phase synthesis. Lipids. Classification. Triglycerides: saturated and unsaturated fatty acids. Oils and fats. Soaps and detergents. Structure of phospholipids, prostaglandins, terpenes and steroids. Nucleic acids. Purine and pyrimidine nitrogenous bases, nucleosides, nucleotides, DNA, RNA (hint).

The student should have a good knowledge of the fundamental topics taught in the first-year General and Inorganic Chemistry course: periodic table; electronegativity and electronic configuration; chemical bonds, hybridization, resonance; Broensted acids and bases; Lewis acids and bases.

Testi adottati: J. McMurry CHIMICA ORGANICA Piccin, IX edizione (2017) W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote CHIMICA ORGANICA EdiSES, V edizione (2015) (e-book compreso nel prezzo della copia cartacea; disponibilità: 18 mesi dalla attivazione) K. P. C. Vollhardt, N. Schore CHIMICA ORGANICA Zanichelli, quarta Edizione (2021) P. Y. Bruice CHIMICA ORGANICA EdiSES, III edizione (2017) (e-book compreso nel prezzo della copia cartacea; disponibilità: 18 mesi dalla attivazione)

Lessons are given with the support of slides and explanations on the blackboard. During lessons students are encouraged to participate and a proper number of lessons will be devoted to exercises conceived as a tool to consolidate the new topics and as an opportunity for additional explanations and clarifications.

It is strongly recommended to attend lessons. The exam is a compulsory basis for other programs.

The examination consists of a written test followed by an oral test. The written examination consists of two parts: 1) a 10-question multiple-choice quiz that may contain theoretical questions and exercises on the topics covered in the lecture; some of the questions may require a brief answer; 2) two open-ended problems (total duration of examination 90 minutes). Admission to the oral examination is possible if the mark in the written examination is 17/30 or higher. The oral examination lasts approximately 30 minutes and consists of 3 questions on the entire syllabus. To access the written examination, students must register on e-learning and on INFOSTUD. To access the oral examination, students must register on e-learning.

Lessons are given with the support of slides and explanations on the blackboard. During lessons students are encouraged to participate and a proper number of lessons will be devoted to exercises conceived as a tool to consolidate the new topics and as an opportunity for additional explanations and clarifications.

Organic Chemistry (9 CFU) (Canale 1); Program 2024-2025 Introduction to Organic Chemistry: electronic structure of atoms; Lewis bond model; electronegativity; dipole moment of bonds and molecules. Covalent bonding according to the valence bond model: hybridization of atomic orbitals. Formal charge. Resonance. Intermolecular interactions (dipole-dipole interactions, hydrogen bonding, van der Waals forces); polarizability; solubility and physical properties of organic compounds. Acid-base properties: acidity and basicity according to Brønsted-Lowry (Ka and pKa) and according to Lewis. Alkanes. Structural isomers. Molecular models. Perspective and projective formulas. Alkyl groups. Nomenclature. Physical properties. Conformation of alkanes (Newman and sawhorse representations). Cycloalkanes. Nomenclature. Physical properties. Cis-trans isomers. Ring tension. Conformation of cycloalkanes and substituted cycloalkanes. Chirality. Chiral and achiral molecules. Stereocenter (definition). Stereoisomers and Enantiomers. Absolute configuration R/S. Molecules with more than one stereocenters: diastereoisomers and meso compounds. Fischer projections. Properties of stereoisomers. Optically active compounds (observed and specific rotation). Alkenes. Structure and nomenclature. Geometric isomers (cis/trans and E/Z notations). Alkene reactions. Electrophilic additions to double bonds: hydrogen halide additions. Relative stability of carbocations. Rearrangement of carbocations. Hydration reaction of alkenes: acid-catalyzed process. Acid-catalyzed addition of alcohols to alkenes; chlorine and bromine addition to alkenes: halonium ion. Alkene oxidations: glycol formations, epoxidation, ozonolysis. Alkene reductions. Heat of hydrogenation and alkene stability. Regioselectivity and stereoselectivity in addition reactions to alkenes. Alkynes. Structure and nomenclature. Reactivity of alkynes. Addition of H 2 , X 2 , HX and hydration. Acidity of alkynes. Alkylation of acetylide anions. Alkyl halides. Structure and nomenclature. Preparation: halogenation of alkanes, addition of X 2 and HX to alkenes, allyl bromination, formation from alcohols. Aliphatic nucleophilic substitution. SN2 and SN1 mechanisms: stereochemistry and kinetic evidence. Factors affecting the rate of SN2 and SN1 processes: structure of nucleophile, RX, leaving group, and solvent effect. Examples of SN2 and SN1 processes. Beta-elimination reactions. Zaitzev's rule, E2 and E1 mechanism. E2 and E1 comparison. Stereochemistry of E2. Alcohols. Structure, nomenclature and physical properties. Acid-base reactions. Preparation of alcohols from alkenes and alkyl halides. Reactions of alcohols: conversion to alkyl halides and tosylates. Reactions of alcohols: acid-catalyzed dehydration. Ethers. Structure, nomenclature and physical properties. Preparation of ethers: Williamson synthesis. Reactions of ethers: cleavage with acids. Epoxides. Structure, nomenclature and their reactivity in acid- or base-catalyzed processes. Benzene and benzene derivatives. Nomenclature. Resonance energy and aromaticity. Mono- and polysubstituted derivatives. Polycyclic and heterocyclic aromatic compounds. Electrophilic aromatic substitution: halogenation, nitration, sulfonation, Friedel-Crafts alkylation and acylation reactions. Substituent effects (activation/deactivation and directing effects in electrophilic aromatic substitution processes on substituted benzene rings). Oxydation of alkylbenzenes. Ketones and aldehydes. Nomenclature. Structural characteristics of the carbonyl group. Preparation of aldehydes and ketones. Nucleophilic addition to carbonyl carbon: addition of HCN, alcohols, amines, Grignard reagents. Oxidation and reduction of aldehydes and ketones. Carboxylic acids. Structure and nomenclature. Physical properties. Acidity and effect of substituents. Preparation of carboxylic acids. Reduction of carboxylic acids. Nitriles. Nomenclature. Hydrolysis of nitriles. Derivatives of carboxylic acids. Structure and nomenclature. Conversion of carboxylic acids to acyl chlorides, anhydrides, esters, amides and alcohols. Acyl nucleophilic substitution. Reactions of acyl halides, anhydrides, esters and amides. Enolate anions. Keto-enol tautomeria. Racemization in alpha to carbonyl. Halogenation in alpha position. Acidity of hydrogens in alpha to a carbonyl. Formation of enolates. Alkylation of enolates. Malonic synthesis. Acetoacetic synthesis. Aldolic condensation: symmetrical, cross-linked and intramolecular aldolic reactions. Amines. Classification of amines. Nomenclature. Basicity of amines. Structure-basicity relationship in aliphatic, aromatic and aromatic heterocyclic amines. Preparation of amines. Reactions of amines. Pyridine, pyrrole, imidazole. Carbohydrates. Classification. D- and L-monosaccharides: Fischer projections. Hemiacetal cyclic structure: Haworth formulas and chair conformations. Epimers and anomers. Mutarotation. D- Glucose, D-fructose, D-ribose, D-mannose, D-galactose. Monosaccharide reactions: glycoside formation, reduction and oxidation. Disaccharides: maltose, cellobiose, lactose, sucrose. Polysaccharides: starch, glycogen and cellulose. Amino acids. Classification. alpha-natural amino acids. Acid-base properties. Isoelectric point. Synthesis of amino acids. Polypeptides and proteins: primary, secondary (alpha-helix and structure beta sheet), tertiary and quaternary structure. Chemical synthesis of polypeptides: protecting and activating groups. Hints on solid-phase synthesis. Lipids. Classification. Triglycerides: saturated and unsaturated fatty acids. Oils and fats. Soaps and detergents. Structure of phospholipids, prostaglandins, terpenes and steroids. Nucleic acids. Purine and pyrimidine nitrogenous bases, nucleosides, nucleotides, DNA, RNA (hint).

The student should have a good knowledge of the fundamental topics taught in the first-year General and Inorganic Chemistry course: periodic table; electronegativity and electronic configuration; chemical bonds, hybridization, resonance; Broensted acids and bases; Lewis acids and bases.

Testi adottati: J. McMurry CHIMICA ORGANICA Piccin, IX edizione (2017) W. H. Brown, B. L. Iverson, E. V. Anslyn, C. S. Foote CHIMICA ORGANICA EdiSES, V edizione (2015) (e-book compreso nel prezzo della copia cartacea; disponibilità: 18 mesi dalla attivazione) K. P. C. Vollhardt, N. Schore CHIMICA ORGANICA Zanichelli, quarta Edizione (2021) P. Y. Bruice CHIMICA ORGANICA EdiSES, III edizione (2017) (e-book compreso nel prezzo della copia cartacea; disponibilità: 18 mesi dalla attivazione)

Lessons are given with the support of slides and explanations on the blackboard. During lessons students are encouraged to participate and a proper number of lessons will be devoted to exercises conceived as a tool to consolidate the new topics and as an opportunity for additional explanations and clarifications.

It is strongly recommended to attend lessons. The exam is a compulsory basis for other programs.

The examination consists of a written test followed by an oral test. The written examination consists of two parts: 1) a 10-question multiple-choice quiz that may contain theoretical questions and exercises on the topics covered in the lecture; some of the questions may require a brief answer; 2) two open-ended problems (total duration of examination 90 minutes). Admission to the oral examination is possible if the mark in the written examination is 17/30 or higher. The oral examination lasts approximately 30 minutes and consists of 3 questions on the entire syllabus. To access the written examination, students must register on e-learning and on INFOSTUD. To access the oral examination, students must register on e-learning.

Lessons are given with the support of slides and explanations on the blackboard. During lessons students are encouraged to participate and a proper number of lessons will be devoted to exercises conceived as a tool to consolidate the new topics and as an opportunity for additional explanations and clarifications.