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, oils and fats.
Course Content - Last names M-Z
Ibridazione e forma delle molecole. Acidità, basicità, carattere elettrofilo e nucleofilo dei composti organici. Reazioni redox. Principali classi di composti organici: loro sintesi e reattività. Reazioni di addizione, eliminazione e sostituzione. Isomeria strutturale e stereoisomeria. Composti organici biologicamente importanti: amminoacidi, peptici, proteine, mono-, di- e polisaccaridi, oli e grassi.
Textbooks:
J. McMurry, Fondamenti di Chimica Organica, 3a edizione 2009, Zanichelli, Bologna.
W. Brown, T. Poon, Introduzione alla Chimica Organica, 4a edizione 2009, EdiSES, Napoli.
J. Gorzynski Smith, Fondamenti di Chimica Organica, 1a edizione 2009, McGraw-Hill, Milano.
Textbooks:
J. McMurry, Fondamenti di Chimica Organica, 3a edizione 2009, Zanichelli, Bologna.
W. Brown, T. Poon, Introduzione alla Chimica Organica, 4a edizione 2009, EdiSES, Napoli.
J. Gorzynski Smith, Fondamenti di Chimica Organica, 1a edizione 2009, McGraw-Hill, Milano.
Learning Objectives - Last names A-L
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.
Learning Objectives - Last names M-Z
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..
Prerequisites - Last names A-L
Courses required: General and Inorganic Chemistry
Courses recommended: Mathematics, Physics
Prerequisites - Last names M-Z
Courses required: General and Inorganic Chemistry
Courses recommended: Mathematics, Physics
Teaching Methods - Last names A-L
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:120
Contact hours for: Lectures (hours): 50
Contact hours for: Laboratory (hours): 0
Contact hours for: Laboratory-field/practice (hours): 0
Seminars (hours): 0
Stages: 0
Intermediate examinations: 0
Teaching Methods - Last names M-Z
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:120
Contact hours for: Lectures (hours): 50
Contact hours for: Laboratory (hours): 0
Contact hours for: Laboratory-field/practice (hours): 0
Seminars (hours): 0
Stages: 0
Intermediate examinations: 0
Further information - Last names A-L
Usually Monday 3.00-6.00 pm. Otherwise agreement between students and teacher.
Further information - Last names M-Z
Orario di ricevimento
Normalmente il lunedì dalle 15.00 alle 18.00. Altrimenti accordi tra studenti e docente.
Type of Assessment - Last names A-L
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.
Type of Assessment - Last names M-Z
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 program - Last names A-L
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. pi-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.
alpha-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: alpha and beta forms. Mutarotation. Stability of alpha- and beta- glucose. Disaccharides and polysaccharides.
Course program - Last names M-Z
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. pi-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.
alpha-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: alpha and beta forms. Mutarotation. Stability of alpha- and beta- glucose. Disaccharides and polysaccharides.