B006416 - ORGANIC CHEMISTRY

Italian

Italian

Knolewdge acquired:
The course is aimed to provide the students with a basic knowledge of organic chemistry. The knowledge of this subject is a fundamental requirement for understanding the complex biochemical mechanisms found in living organisms, such as metabolism and energetic balance, formation of secondary metabolites, action of enzymes and biologically active substances, etc.
Competence acquired:
Ability to recognize the main classes of organic compounds according to the functional groups linked in the molecule. Evaluation of the possibility of transforming the existing functional groups and adding new groups in order to increase the reactivity and/or carry out the preparation of a target compound. General view of the most important classes of organic reactions and related reaction mechanisms.
Skills acquired (at the end of the course):
At the end of the course the students will acquire the ability of writing the structures of organic molecules on the basis of both trivial and IUPAC names. The students, on the basis of the structure of a given compound, will be able to predict its properties, such as acidity, basicity, electrophilic and/or nucleophilic character, optical activity, etc. Furthermore, they will acquire the capability of understanding the general problems related to reactivity of organic compounds, such as formation of by-products, stereo- and regioisomers, etc..

Knolewdge acquired:
The course is aimed to provide the students with a basic knowledge of organic chemistry. The knowledge of this subject is a fundamental requirement for understanding the complex biochemical mechanisms found in living organisms, such as metabolism and energetic balance, formation of secondary metabolites, action of enzymes and biologically active substances, etc.
Competence acquired:
Ability to recognize the main classes of organic compounds according to the functional groups linked in the molecule. Evaluation of the possibility of transforming the existing functional groups and adding new groups in order to increase the reactivity and/or carry out the preparation of a target compound. General view of the most important classes of organic reactions and related reaction mechanisms.
Skills acquired (at the end of the course):
At the end of the course the students will acquire the ability of writing the structures of organic molecules on the basis of both trivial and IUPAC names. The students, on the basis of the structure of a given compound, will be able to predict its properties, such as acidity, basicity, electrophilic and/or nucleophilic character, optical activity, etc. Furthermore, they will acquire the capability of understanding the general problems related to reactivity of organic compounds, such as formation of by-products, stereo- and regioisomers, etc..

The course aims to provide students with a basic knowledge of organic chemistry, with particular regard to biological implications of organic molecules. The basic concepts of structure and bonding are introduced, the structure and reactivity of the main functional groups, with a sketch of the fundamental reaction mechanisms. The last part regards the chemistry of biomolecules (lipids, carbohydrates, amino acids, peptides and proteins, nucleic acids).

The course aims to provide students with a basic knowledge of organic chemistry, with particular regard to biological implications of organic molecules. The basic concepts of structure and bonding are introduced, the structure and reactivity of the main functional groups, with a sketch of the fundamental reaction mechanisms. The last part regards the chemistry of biomolecules (lipids, carbohydrates, amino acids, peptides and proteins, nucleic acids).

Courses to be used as requirements
Courses required: General and Inorganic Chemistry
Courses recommended: Mathematics, Physics

Courses required: General and Inorganic Chemistry

CFU: 6
Total hours of the course (including the time spent in attending lectures, seminars, private study, examinations, etc...): 150
Hours reserved to private study and other indivual formative activities:102
Contact hours for: Lectures (hours): 48
Contact hours for: Laboratory (hours): 0
Contact hours for: Laboratory-field/practice (hours): 0
Seminars (hours): 0
Stages: 0
Intermediate examinations: 0

CFU: 6
Total hours of the course: 150
Hours reserved to private study and other indivual formative activities: 102
Contact hours for: Lectures (hours): 48

Exam modality: Discussion on the general properties of a class (more classes)of organic compounds. Solving of problems related to the reactivity, reaction mechanisms. Regio- and stereoisomerism.
Programme (short version for Diploma Supplement):
Hybridization and shapes of the molecules. Acidity, basicity, electrophilic and nucleophilic character of organic compounds. Redox reactions. Main classes of organic compounds: their synthesis and reactivity. Addition, elimination, and substitution reactions. Structural and stereoisomerism. Biologically relevant organic compounds: amino acids, peptides, proteins, mono- di-, and polysaccharides, lipids.

Exam modality: Discussion on the general properties of a class (more classes)of organic compounds. Solving of problems related to the reactivity, reaction mechanisms. Regio- and stereoisomerism.

Course Contents (detailed program): Introduction: beginning and development of organic chemistry. Fundamental discoveries. Organic compounds and their interest from economical, social, and cultural points of view.
Hybridization of the carbon atom and shape of the molecules. Bondsethylene and acetylene. Bond length and strength. Acid-base theories. Inductive and resonance effects.
Structure and stability of carbocations. Hyper-conjugative effects.
Classification of the organic chemistry reactions. Electrophiles and nucleophiles: definition, analogies and differences between acid-base and E/N behaviour. Acid (protic and Lewis) attack onto unsaturated species: activation of the carbonyl group and double carbon-carbon bond.
Alkanes: definition, nomenclature and physical properties. Structural isomerism. Reactivity. General remarks on the reactions: kinetic plots, definition of reaction coordinate, transition state, and reaction intermediate. Hammond postulate. Newman projection formulas, conformational analysis. Cycloalkanes: stability and combustion enthalpies, angle bond strains and torsion strains. Conformational analysis of cycloalkanes.
Alkenes: definition, nomenclature, and physical properties. Isomerism. Structure and stability. Structural and stereo- isomerism (cis/trans, E/Z). Reactivity. Markovnikov’s rule.
Dienes: definition, classification, and nomenclature. Structural features of 1,2- and 1,3-dienes. Diels-Alder cycloadditions.
Alkynes: structural features and nomenclature. Acidity.
Aromatic compounds. Meaning of the term. Pioneering studies on benzene and its derivatives. Reactivity of benzene. Kekulé formulas. Empirical resonance energy. Huckel’s rule. Electrophilic substitution reactions. Kinetic plots of the main aromatic electrophilic substitutions. Activating and deactivating groups toward aromatic electrophilic substitution. Analysis of inductive and conjugative effects. Orientation. Ortho/para ratio in disubstituted derivatives of benzene. Elimination-addition reactions via benzene, nucleophilic substitutions SN1Ar and SN2Ar: decomposition of diazonium salts.
Stereoisomerism. Diastereoisomers and enantiomers: definition and examples. Symmetry elements. Concept of chirality. Nomenclature of diastereoisomers (geometric isomers) by means of E/Z method. Principles of polarimetry. Specific rotation and optical purity. Optically active compounds with one stereogenic center: attribution of the stereochemistry by means of the relative method D/L and the absolute method R/S. Compounds with two stereogenic centers. Compounds having two equivalent stereogenic centers: meso isomers. Prochirality. Resolution of racemic mixtures. Chirality in compounds without stereogenic centers.
Aliphatic nucleophilic substitutions SN1 and SN2: features of nucleophiles and leaving groups, stereochemical aspects, circumstances that favor the SN1 and SN2. Substitutions vs. eliminations.
Halohydrocarbons: definition, nomenclature, physical properties. Reactivity.
Grignard’s reagents: preparation and reactions with polar multiple bonds. Reaction with aldehydes, ketones
Alcohols: definition, classification, nomenclature, physical properties. Preparation of 1,2-diols: methods and stereochemical aspects. Glycerol.
Esters: definition. Esters of carboxylic acids. Formation according to Fischer. Acid and alkaline (saponification) hydrolysis. Mechanism of alkaline hydrolysis. Stereochemical proofs of the mechanism. Waxes, oils, and fats. Esters of non-carboxylic acids. Phospholipids.
Ethers: definition, nomenclature, and physical properties. Epoxides: preparation and reactivity.
Phenols: definition, nomenclature, and reactivity. Electrophilic substitutions on the ring by weak electrophiles.
Sulfur-containing compounds. Thiols, thiophenols and thioethers. Oxidation of thiols and thioethers.
Carbonyl compounds: definition, nomenclature of aldehydes and ketones, physical properties. Reactivity of the carbonyl group. Reaction with nitrogen, carbon, oxygen, and sulfur nucleophiles. Addition of hydride ion. Cannizzaro reaction. Reactions involving the carbon adjacent to the carbonyl: aldol reaction and mixed aldol reactions.
Carboxylic acids: definition, nomenclature, and physical properties. Reactions of carboxylic acids: formation of esters and other functional derivatives. Dicarboxylic acids, hydroxyacids and oxoacids.
Amines: definition, classification, nomenclature, and physical properties. Basicity of alkylamines and arylamines in comparison with ammonia. Reactions of amines with electrophiles.
-Amino acids: definition, nomenclature, and physical properties. Classification according to chemical and biological criteria. Structure and amphoteric character, isoelectric point. Stereochemistry. Peptides and their synthesis: use of protecting groups. Proteins.
Carbohydrates: definition and classification. Monosaccharides belonging to D series. Fischer projection formulas. Chain elongation of an aldose (Kiliani-Fischer). Shortening the chain of an aldose (Ruff and Wohl degradations). Ancient and actual meaning of the term epimeric sugars. Reaction of monosaccharides with Tollens, Fehling, and Benedict reactants. Glucose:  and forms. Mutarotation. Stability of -and - glucose. Disaccharides and polysaccharides.

J. Gorzynski Smith, Fondamenti di Chimica Organica, McGraw-Hill, Milano.
J. McMurry, Fondamenti di Chimica Organica, Zanichelli, Bologna.
W. Brown, T. Poon, Introduzione alla Chimica Organica, EdiSES, Napoli.
Material provided by the teacher

J. Gorzynski Smith, Fondamenti di Chimica Organica, McGraw-Hill, Milano.
J. McMurry, Fondamenti di Chimica Organica, Zanichelli, Bologna.
W. Brown, T. Poon, Introduzione alla Chimica Organica, EdiSES, Napoli.
Material provided by the teacher

Frequency of lectures, practice and lab:
Highly recommended
Teaching tools:
Molecular models.
Office hours:
By e-mail contact with the teacher.

Frequency of lectures, practice and lab:
Highly recommended
Teaching tools:
Molecular models.
Office hours:
By e-mail contact with the teacher.