Natural Sciences

Activity type

Discipline chimiche

SSD

CHIM/06

Year

N/D

Semester

N/D

CFU

4

Hours distribution

40 classroom hours

Lecturers

FRANCESCA GHIRGA

Activity type

Discipline chimiche

SSD

CHIM/03

Year

N/D

Semester

N/D

CFU

5

Hours distribution

50 classroom hours

Lecturers

Academic objectives: knowledge of fundamental general and inorganic chemistry in order to give a solid background to the students and allow them to handle properly various subjects related to chemistry during the subsequent courses. Another objective is to stimulate curiosity toward matter and properties.
Knowledge of electronic structure and valence properties of the elements of the periodic table. Properties of matter related to the different states (gas, liquid, solid, crystals and so on). Basic concepts of thermodynamics. Ability to associate name of chemicals to structure and physical properties, in relation to the nature of intra and intermolecular chemical bonds. Knowledge of structure and properties of most common substances and ability to distinguish different classes.

Expected learning outcomes
Organic chemistry is a chemistry discipline involving the scientific study of the structure, reactivity, properties and applications of compounds which are formed mainly by carbon atoms, forming covalent bonds, both from natural and artificial sources The general objective, is to provide students with the knowledge and competences necessary to understand the structure, reactivity and synthetic methods of different functional groups, and the mechanisms of organic reactions. For a Natural Science student, this learning is essential, to understand physical or macroscopic properties of matter on molecular basis and to know the role and impact of organic chemistry in natural sciences, modern technology and society.
This knowledge will allow the student to be able to understand biochemistry, genetics and physiology, crucial topics in different next courses.

Dublin Descriptors
The Organic Chemistry course is devoted to provide students with the adequate knowledge to be independent in solving the examination problems or exercises.
This ability will be acquired by the means of frontal lesson and guided exercitations that will be organized in ascending order of the difficulties they pose.
Teaching materials, available on line will support students during the lessons even though studying the recommended text book is essential to acquire the skills and the competence that are necessary to perform the final exam.
In order to improve the exposure ability, students will be constantly encouraged to communicate their ideas to both specialists and non specialists audiences. The Erasmus programme will enable students to improve their communications skills, by exchanging informations, problems and solutions.
The specific objectives consist in acquiring the following knowledge and expertise:
1) to understand the importance of stereochemistry on the reactivity of organic compounds;
2) to understand the relationship between structure and reactivity for the different functional groups;
3) to acquire the basic knowledge of organic chemistry in order to understand the basic mechanism of organic reactions.
4) to acquire the basic knowledge of the organic synthesis
5) to apply the main concepts of stereochemistry to the reactivity of organic compounds.
6) to predict the reactivity and the physical properties of organic compounds.
7) to speculate about mechanistic aspect of the organic reactions.
8) to design the synthesis of organic molecules through their retrosynthetic analysis.

The specific objectives of the course include acquiring the following knowledge and skills: 1)understanding the relationship between structure and physical properties of the most common classes of organic compounds; 2)understanding the reactivity of the most common functional groups; 3)learning and rationalizing the most common reaction mechanisms in organic chemistry; 4) acquiring basic knowledge related to the synthesis of organic compounds; 5)formulating sound mechanistic hypotheses for simple organic reactions; 6) applying the fundamental concepts of organic chemistry to biological systems.

The student is expected to have a good command of the fundamentals of chemistry, including nomenclature, chemical reactions, stoichiometry, molecular structure, electronic structure, the valence bond model, thermodynamic state functions, and a general overview of kinetics. Such concepts are briefly re-introduced whenever necessary. Nevertheless, their knowledge is essential to the understanding of the material.

Module: INORGANIC CHEMISTRY

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)



Module: ELEMENTS OF ORGANIC CHEMISTRY
N/D

Module: INORGANIC CHEMISTRY
Theory and Problems of Organic Chemistry, H. Meislich H. Nechamkib, J. Sharefkin, 2nd edition.
alternatively:
W. H. Brown “Chimica Organica” Ed. Edises 2010
J. Mc Murry “Chimica Organica” 9 Ed. Ed. Piccin 2017



Module: ELEMENTS OF ORGANIC CHEMISTRY
N/D

Module: INORGANIC CHEMISTRY
N/D
Module: ELEMENTS OF ORGANIC CHEMISTRY
N/D

The course is held in the form of frontal lessons. The use of a blackboard -either a traditional, or a digital one- allows the sudents to easily take notes. Only particularly complex structures, pictures and tables are projected.

Attendance is not mandatory, but strongly suggested

The written exam measures the student's ability to correctly represent organic molecules (structure and nomenclature), as well as their knowledge on the reactivity of the most common classes of organic compounds.
The oral exam assesses the ability to present the course concepts clearly and to identify the connections between the various topics covered.

1) Given a molecular structure, identify the functional groups and provide the IUPAC name;
2) in a chemical reaction, given any two of the following—reactants, products, or reaction conditions—propose the missing one. (Example: Given reactants and products, 3) identify the reaction conditions.);
4) propose a synthetic route for a simple organic compound;
5) predict the product distribution of a chemical reaction based on experimental conditions (temperature, solvent, base/nucleophile, or different functional groups present on the substrate);
6) identify the chemical basis for the biological role of a given compound.

Module: INORGANIC CHEMISTRY

• General Chemistry recap (2 hours) 
  • Books: Theory and Problems of Organic Chemistry, H.
    
    Meislich H. Nechamkib, J. Sharefkin, 2nd edition. Chapter 1,2


• Hydrocarbons (9 hours) 
  • Books: Theory and Problems of Organic Chemistry, H.
    
    Meislich H. Nechamkib, J. Sharefkin, 2nd edition. Chapter 4-11,19


• Alkyl compounds (6 hours) 
  • Books: Theory and Problems of Organic Chemistry, H.
    
    Meislich H. Nechamkib, J. Sharefkin, 2nd edition. Chapter 13,14,18


• Carbonyl and carboxyl compounds (5 hours) 
  • Books: Theory and Problems of Organic Chemistry, H.
    
    Meislich H. Nechamkib, J. Sharefkin, 2nd edition. Chapter 15-17


• Biological macromolecules (4 hours)
  • Books: Theory and Problems of Organic Chemistry, H.
    
    Meislich H. Nechamkib, J. Sharefkin, 2nd edition. Chapter 21,22


• Summary and exercises (12 hours) 
  • Books: course notes provided by the professor