Natural Sciences

General Chemistry recap (4 hours) Periodic properties of elements- Chemical bonds. Intermolecular forces. Acidity and basicity (Arrhenius, Lowry-Brönsted and Lewis definitions): pka, equilibtrium. Factors influencing Lowry-Brönsted acidity: electronegativity, inductive effect, resonance, polarizability. Hydrocarbons (9 hours) Alkanes and cycloalkanes (2 hours) sp3 hybridization. Nomenclature, structure and structural isomers, physical properties, solubility. Conformation of linear alkanes and Newman projections, torsional strain. Conformation of cycloalkanes, angular strain, chair conformations of cyclohexane. Reactivity: combustion. Stereochemistry (2 hours) Chirality. Stereogenic center and symmetry plane. Enantiomers and diasteroisomers. Meso-forms. Nomenclature R, S (Cahn, Ingold, and Prelog priority rules). Optical rotation. Racemates. Chirality in biologal molecules. Alkenes and Alkynes (2 hours) sp2 and sp hybridization. Nomenclature, structure, geometric stereoisomerism (cis and trans, E and Z), physical properties. Reactivity: addition of alogen-hydric acids and water, carbocations, mechanism and stereochemistry. Aromatic compounds (3 hours) Conjugation and aromaticity. Huckel rule: Aromatic, antiaromatic and non aromatic compounds. Heteroaromatics. Nomenclature and physical properties (color). Electrophilic aromatic substitution: mechanism, halogenation, resonance. Alkyl compounds (6 hours) Alkyl halides (4 hours) Nomenclature, structure, physical properties. Nucleophilic substitution (SN2 and SN1): mechanism, stereochemistry. Competition between SN2 and SN1: nucleophilicity (basicity, polarizability, steric hindrance), substrate structure, solvent. beta-Elimination (E1 and E2). mechanism, regiochemistry. E1 vs E2: influence of the alkyl halide. SN1 vs E1 and SN2 vs E2 Alcohols, ethers and amines (2 hours) Nomenclature, physical properties. Reactivity: acidity and basicity. Phenols and anilines. Carbonyl and carboxyl compounds (5 hours) Aldehydes and ketones (3 hours) Nomenclature, physical properties. Reactivity: addition to the carbonyl: reaction with boron and aluminum hydrides, water, alcohols. Addition-elimination reactions: condensation with primary amines. Keto-enol tautomerism (base-catalyzed), nucleophilicity of the enolate. Carboxylic acids and derivatives (2 hours) Esters, amides. Nomenclature, physical properties. Carboxylic acids reactivity: acidity, Fischer esterification. Reactivity of acid erivatives: hydrolysis, synthesis of amides. Biological macromolecules (6 hours) Carbohydrates (2 hours) Structure of common sugars. D, L series. Fischer formulas. Cyclic structure of monosaccharides. Anomers, epimers. Mutarotation. Polysaccharides: starch, cellulose. Proteins (2 hours) Aminoacids structure and chirality. Acid-base properties. Peptide bond. Proteins: primary, secondary, tertiary structure. Lipids (1 hour) Triglycerides. Saturated and unsaturated fatty acids. Phospholipids. Aggregation in micelles, vesicles, membranes. Nucleic Acids (1 hour) Nucleosides and nucleotides. RNA and DNA. Double helix. Summary and exercises (12 hours)

Students are expected to have basic knowledge of General and Inorganic Chemistry and, in particular, of the following fundamental concepts: atomic structure and orbitals, periodic properties of elements, hybridization, resonance, fundamental principles of thermodynamics and kinetics, chemical equilibrium, acidity, and basicity.

B. Botta, CHIMICA ORGANICA ESSENZIALE, Edi-Ermes, 2° Ed. in alternativa: W. H. Brown “Chimica Organica” Ed. Edises 2010 J. Mc Murry “Chimica Organica” 9 Ed. Ed. Piccin 2017

Attendance at lectures and tutorials is strongly suggested but is not mandatory.

The acquisition of the course credits (CFU) is subject to the successful completion of the final examination, which is scheduled during the official exam sessions published on the Infostud platform. Midterm assessments with partial exemption are also planned. The final examination consists of a written test, which serves as a prerequisite for the oral examination (the oral exam is optional for students who achieve a score higher than 22 in the written test). The written exam assesses the student's ability to apply the principles of structure and reactivity of organic compounds to problem-solving. The oral exam evaluates the student's overall knowledge of the course content, clarity of expression, and ability to make connections and critically reason through the topics covered during the lectures. Students who pass both midterm tests are exempt from written and oral exams. Passing only one midterm test exempts the student from the written exam. The written exam will be held concurrently with the written exam for the General and Inorganic Chemistry module. There is no limit to the number of exam attempts allowed during the academic year.

Frontal lectures (3 CFU): 30 hours, Tutorials (1 CFU): 12 hours. The course (4 CFU) consists of lectures integrated with tutorials. The lectures occur in classrooms with devices suitable for projecting course slides, available to enrolled students on the La Sapienza E-learning platform. The tutorials, provided throughout the course duration, cover all topics addressed during the theoretical lectures and prepare students for the written exam. Various recap sessions are planned, and exercises representative of those administered in the exams are discussed.

Richiami di Chimica Generale (4 ore) Proprietà periodiche degli elementi. Legame chimico. Legami singoli e multipli. Forze intermolecolari. Acidità e basicità (Arrhenius, Lowry-Brönsted e Lewis): pka, equilibrio. Fattori che influenzano la forza degli acidi e delle basi di Lowry-Brönsted: elettronegatività, effetto induttivo, risonanza, polarizzabilità. Idrocarburi (9 ore) Alcani e cicloalcani (2 ore). Ibridazione del carbonio sp3. Nomenclatura, struttura e isomeri strutturali, proprietà fisiche, solubilità. Conformazione di alcani lineari e proiezioni di Newman, tensione torsionale. Conformazione dei cicloalcani, tensione angolare, conformazioni a sedia del cicloesano. Reattività: combustione (cenni). Stereochimica (2 ore) Chiralità. Centro stereogenico e piano di simmetria. Enantiomeri e diastereoisomeri. Forme meso. Nomenclatura: il sistema R-S (Cahn, Ingold e Prelog). Attività ottica. Racemi. Chiralità nelle molecole biologiche. Alcheni e Alchini (2 ore) Ibridazione del carbonio sp2 e sp. Legami multipli. Nomenclatura, struttura, proprietà fisiche, stereoisomeria geometrica (cis e trans, E e Z). Reattività: addizione di acidi alogenidrici e H2O, carbocationi, meccanismo e stereochimica. I composti aromatici (3 ore) Coniugazione e aromaticità. Regola di Huckel: Composti aromatici, antiaromatici e non aromatici. Composti eterociclici aromatici (pirrolo e piridina). Nomenclatura e proprietà fisiche (colore). Reattività: sostituzione elettrofila aromatica: meccanismo dell’alogenazione. Risonanza. Composti alchilici (6 ore) Alogenuri alchilici (4 ore) Nomenclatura, struttura, proprietà fisiche. Sostituzione nucleofila alifatica (SN2 e SN1): meccanismo, stereochimica. Competizione tra SN1 e SN2: Nucleofilia (basicità, polarizzabilità, ingombro sterico), solvente, substrato. beta-Eliminazione (E1 e E2): meccanismo, regiochimica. Competizione tra E1 e E2: struttura dell’alogenuro alchilico. Competizione tra SN e E effetto del substrato, del nucleofilo/base, del solvente. Alcoli, eteri, ammine (2 ore) Nomenclatura, proprietà fisiche. Reattività: proprietà acido-base di alcoli e ammine. Effetto dell’aromaticità sull’acidità. Composti carbonilici, acidi carbossilici e loro derivati (5 ore) Aldeidi e chetoni (3 ore) Nomenclatura, proprietà fisiche. Reattività: Addizione al carbonile: Reazione con idruri del boro e dell’alluminio, alcoli. Addizione-eliminazione: condensazione con ammine primarie. Tautomeria cheto-enolica in ambiente basico. Nucleofilia dell’enolato. Acidi carbossilici e derivati (2 ore) Esteri, ammidi. Nomenclatura, proprietà fisiche. Reattività degli acidi: acidità, esterificazione di Fischer. Reazioni dei derivati degli acidi: idrolisi degli esteri, formazione di ammidi. Macromolecole biologiche (6 ore) Carboidrati (2 ore) Struttura di zuccheri comuni. Monosaccaridi D e L. Proiezioni di Fischer. Struttura ciclica dei monosaccaridi. Solubilità. Anomeri, epimeri, mutarotazione. Polisaccaridi (amido, cellulosa) Proteine (2 ore) Struttura degli amminoacidi. Chiralità. Proprietà acide e basiche. Il legame peptidico. Struttura primaria, secondaria, terziaria. Lipidi (1 ora) Trigliceridi. Grassi saturi e insaturi. Fosfolipidi. Aggregazione in micelle, vescicole, membrana cellulare. Acidi nucleici (1 ora) Nucleosidi e nucleotidi. RNA e DNA. Doppia elica. Riepilogo ed esercitazioni (12 ore) SYLLABUS General Chemistry recap (4 hours) Periodic properties of elements- Chemical bonds. Intermolecular forces. Acidity and basicity (Arrhenius, Lowry-Brönsted and Lewis definitions): pKa, equilibrium. Factors influencing Lowry-Brönsted acidity: electronegativity, inductive effect, resonance, and polarizability. Hydrocarbons (9 hours) Alkanes and cycloalkanes (2 hours) sp3 hybridization. Nomenclature, structure, and structural isomers, physical properties, and solubility. Conformation of linear alkanes and Newman projections, torsional strain. Conformation of cycloalkanes, angular strain, chair conformations of cyclohexane. Reactivity: combustion. Stereochemistry (2 hours) Chirality. Stereogenic center and symmetry plane. Enantiomers and diastereoisomers. Meso-forms. Nomenclature R, S (Cahn, Ingold, and Prelog priority rules). Optical rotation. Racemates. Chirality in biological molecules. Alkenes and Alkynes (2 hours) sp2 and sp hybridization. Nomenclature, structure, geometric stereoisomerism (cis and trans, E and Z), physical properties. Reactivity: addition of alogen-hydric acids and water, carbocations, mechanism and stereochemistry. Aromatic compounds (3 hours) Conjugation and aromaticity. Huckel rule: Aromatic, antiaromatic and non aromatic compounds. Heteroaromatics. Nomenclature and physical properties (color). Electrophilic aromatic substitution: mechanism, halogenation, resonance. Alkyl compounds (6 hours) Alkyl halides (4 hours) Nomenclature, structure, physical properties. Nucleophilic substitution (SN2 and SN1): mechanism, stereochemistry. Competition between SN2 and SN1: nucleophilicity (basicity, polarizability, steric hindrance), substrate structure, solvent. beta-Elimination (E1 and E2). mechanism, regiochemistry. E1 vs E2: influence of the alkyl halide. SN1 vs E1 and SN2 vs E2 Alcohols, ethers and amines (2 hours) Nomenclature, physical properties. Reactivity: acidity and basicity. Phenols and anilines. Carbonyl and carboxyl compounds (5 hours) Aldehydes and ketones (3 hours) Nomenclature, physical properties. Reactivity: addition to the carbonyl: reaction with boron and aluminum hydrides, and alcohols. Addition-elimination reactions: condensation with primary amines. Keto-enol tautomerism (base-catalyzed), nucleophilicity of the enolate. Carboxylic acids and derivatives (2 hours) Esters, amides. Nomenclature, physical properties. Carboxylic acids reactivity: acidity, Fischer esterification. Reactivity of acid derivatives: hydrolysis, synthesis of amides. Biological macromolecules (4 hours) Carbohydrates (2 hours) Structure of common sugars. D, L series. Fischer formulas. Cyclic structure of monosaccharides. Anomers, epimers. Mutarotation. Polysaccharides: starch, cellulose. Proteins (2 hours) Aminoacids structure and chirality. Acid-base properties. Peptide bond. Proteins: primary, secondary, tertiary structure. Lipids (1 hour) Triglycerides. Saturated and unsaturated fatty acids. Phospholipids. Aggregation in micelles, vesicles, membranes. Nucleic Acids (1 hour) Nucleosides and nucleotides. RNA and DNA. Double helix. Summary and exercises (12 hours)

Students are expected to have basic knowledge of General and Inorganic Chemistry and, in particular, of the following fundamental concepts: atomic structure and orbitals, periodic properties of elements, hybridization, resonance, fundamental principles of thermodynamics and kinetics, chemical equilibrium, acidity, and basicity.

B. Botta, CHIMICA ORGANICA ESSENZIALE, Edi-Ermes, 2° Ed. in alternativa: W. H. Brown “Chimica Organica” Ed. Edises 2010 J. Mc Murry “Chimica Organica” 9 Ed. Ed. Piccin 2017

Attendance at lectures and tutorials is strongly suggested but is not mandatory.

The acquisition of the course credits (CFU) is subject to the successful completion of the final examination, which is scheduled during the official exam sessions published on the Infostud platform. Midterm assessments with partial exemption are also planned. The final examination consists of a written test, which serves as a prerequisite for the oral examination (the oral exam is optional for students who achieve a score higher than 22 in the written test). The written exam assesses the student's ability to apply the principles of structure and reactivity of organic compounds to problem-solving. The oral exam evaluates the student's overall knowledge of the course content, clarity of expression, and ability to make connections and critically reason through the topics covered during the lectures. Students who pass both midterm tests are exempt from written and oral exams. Passing only one midterm test exempts the student from the written exam. The written exam will be held concurrently with the written exam for the General and Inorganic Chemistry module. There is no limit to the number of exam attempts allowed during the academic year.

Frontal lectures (3 CFU): 30 hours, Tutorials (1 CFU): 12 hours. The course (4 CFU) consists of lectures integrated with tutorials. The lectures occur in classrooms with devices suitable for projecting course slides, available to enrolled students on the La Sapienza E-learning platform. The tutorials, provided throughout the course duration, cover all topics addressed during the theoretical lectures and prepare students for the written exam. Various recap sessions are planned, and exercises representative of those administered in the exams are discussed.