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. Bio- and pharmaceutically relevant organic compounds: amino acids, peptides, proteins, mono- di-, and polysaccharides, lipids.
During the first lesson it is suggested a large list of recent texts aimed particularly at students of CdS in Pharmacy, both in Italian and English.
Learning Objectives
The course is aimed to provide the students with a basic knowledge of organic chemistry. as an extremely necessary tool to deal with successive courses in particular of biochemistry and pharmaceutical chemistry
Prerequisites
Courses required: General and Inorganic Chemistry
Courses recommended: Mathematics
Teaching Methods
CFU: 9
Total hours of the course (including the time spent in attending lectures, seminars, private study, examinations, etc...): 225
Hours reserved to private study and other indivual formative activities:153
Contact hours for: Lectures (hours): 72
Contact hours for: Laboratory (hours): 0
Frontal lectures with slides and molecular models
Further information
Slides in Powerpoint (course and exercises).
Frequency of lectures is highly recommended
Type of Assessment
Oral examination
Course program
Introduction to Organic Chemistry and general aspects.
What is organic chemistry. Area of interest. Origins of the Organic Chemistry. Definition. The vis vitalis and experience of Wohler. Atomic structure. The periodic table. energy levels and atomic orbitals. Shape of the orbitals. electron distribution. Relative energies of atomic orbitals. chemical bonds. Resonance. Electronegativity and polarity of the bond. Dipole moment. Calculate the formal charge. Calls on the allocation of the degree of oxidation of an element. United hybridization and relative molecular geometry. Classification of chemical bonds. ionic bond. Covalent CT (single, double and triple). Covalent heteropolar. The carbon atom. ground state. excited state. carbon chemical bonds. Representation of an organic structure. Polarity of the molecules. Lewis structures. formal charges. Symbols and definitions related to the writing of the reactions. Possible mechanisms involved in reactions of organic compounds. Reactions that provide a polar mechanism. Reactions involving a radical mechanism. Classification of reactions. substitution reactions. addition reactions. elimination reactions. transposition reactions.
Acids and bases. Acids and bases Arrhenius. Acids and Bases Brønsted-Lowry. acidic pKa and strength. Factors which affect the acidity and the basicity. nature of the solvent. The dissociation of water (Keq, Ka and kw). The definition and the pH scale. Calculation of pH of aqueous solutions of strong acids and bases, weak acids and bases. The hydrolysis of salts. Acids and bases according to Lewis. Electrophiles and nucleophiles.
Review and nomenclature of the main functional groups. Alkanes and cycloalkanes. Classif. hydrocarbons. alkanes electronic structure. structural isomers. IUPAC nomenclature of alkanes. Alkyl radicals. Conformations of alkanes. Natural sources of alkanes. Reactivity of alkanes. Oxidation of alkanes: combustion. Bullets on oxidation and reduction concepts, oxidizing and reducing, balancing of redox reactions. Cycloalkanes and stabilization (torsional strain, steric strain). Conformations of cyclohexane; modes of representation. axial and equatorial bonds. Monosubstituted cyclohexanes. Disubstituted cyclohexanes. conformational analysis. Isomerism and stereoisomerism. constitutional isomers and stereoisomers.
Alkenes. Orbitals. IUPAC Nomenclature of alkenes. Geometric isomerism. Notation cis / trans (examples of cycloalkane). Notation E / Z. industrial sources. Reactivity of alkenes. Mechanism of electrophilic addition reaction. Electrophilic addition of water and of hydrogen halides. Halogenation. Stereochemistry halogenation. Addition of bromine and chlorine. halohydrins of training. The rule of thumb Markovnikov. The carbocations and their stability. theoretical justification of the Markovnikov rule. hydrogenation reaction. Oxidative cleavage of the C-C double bond with KMnO4.
Alkyne. alkyne electronic structure. IUPAC Nomenclature of alkynes. industrial sources. Reactivity of alkynes. Acidity of terminal alkynes. Addition of water and in acidic or basic mechanism.
Isomerism and stereoisomerism. Isomerism: constitutional isomers and stereoisomers. molecular chirality. Symmetry and chirality. Stereogenic centers and centers of chirality. IUPAC recommendations. Enantiomers. cyclic compounds containing a chiral center. Nomenclature of enantiomers: rules of Cahn-Ingold-Prelog and notations R / S. Unconvent. Fischer. Fischer projections. enantiomers optical activity. Measurement of Optical: polarimeter. Specific rotation. Racemic mixture and optical purity. Molecules with two or more centers of chirality. Chiral molecules with two centers of chirality. Erythro and threo forms. Fischer projections of compounds with more centers of chirality. Achiral molecules with two centers of chirality: meso forms. cyclic compounds containing two centers of chirality. Separation of enantiomers: resolution. Resolution for conversion into diastereomers. Resolution by means of enzymes. Elements of symmetry: the center of inversion and rotation axis simple. Rules for manipulating the Fischer projections. Conformational equilibria in solution. Disubstituted derivatives of cyclohexane.
Types of organic reactions. Homolytic or heterolytic breaking and formation of bonds.
Alkyl halides. electronic structure of alkyl halides. IUPAC Nomenclature of alkyl halides. Reactivity of alkyl halides. Aliphatic nucleophilic substitution. Mechanisms of aliphatic nucleophilic substitution. Factors that influence the performance of the monomolecular nucleophilic substitution. Factors affecting the bimolecular nucleophilic substitution. Elimination. organometallic compounds: The Grignard reagent (alkyl / aryl magnesium compounds).
Preparation of compounds organomagnesiaci: because the synthesis of the Grignard reagents must be carried out in an inert atmosphere and in an anhydrous environment. Reactivity of organomagnesiaci compounds. Reactions with aldehydes and ketones: reaction mechanism.
radical reactions: general characteristics. Halogenation of alkanes. Mechanism of the reaction of halogenation of alkanes. Halogenation allyl radical to carbon. Free-radical addition to double bonds. Polymers and polymerization reactions. Examples (PVC et al.)
Alcohols and thiols. Electronic structure of the alcohols. IUPAC nomenclature of alcohols. Definition of alcohol. Preparation of alcohols. Reaction of carbonyl compounds with Grignard reagents. Reactivity of alcohols. The acidity and alkalinity of the alcohols. acid-base reactions. Reactions involving the breaking of the carbon-oxygen bond. Reaction of the alcohol with thionyl chloride. elimination reactions: dehydration of alcohols. Reactions that do not involve the breaking of the carbon-oxygen bond. Transformation of alcohols into esters. Oxidation of alcohols. Obs. of primary alcohols to aldehydes. Obs. of primary alcohols to carboxylic acids and of secondary alcohols to ketones. electronic structure of thiols. IUPAC nomenclature of thiols. Alcohols of practical interest. stereochemical aspects of nucleophilic substitution reactions on alcohols.
Ethers and epoxides. Electronic structure of the ethers. IUPAC nomenclature of ethers. Preparation of the ethers. Intermolecular dehydration of alcohols. Synthesis of symmetrical ethers. Mechanism of the formation of symmetrical ethers by the intermolecular dehydration of alcohols. Williamson synthesis of ethers. IUPAC nomenclature of epoxides.
conjugated systems. Conjugation, resonance and allyl carbocations. resonant examples. The length of the carbon-carbon bond in 1.3-butadiene. conjugated diene. Nomenclature and chemical-physical characteristics of the conjugated dienes. Reactivity of conjugated diene. System description 1,3-butadiene. Electrophilic addition 1.2 and 1.4. Mechanism of the halogen acid addition reaction to conjugated dienes Reaction of Diels-Alder cycloaddition. Mechanism of the reaction of Diels-Alder cycloaddition. Stereo- and regiochemistry of the Diels-Alder reaction. Dienes blocks and cumulative.
aromatic compounds and reactivity. Aroma: concept and criteria Benzene: structure, thermodynamic stability. The resonance energy. Nomenclature of benzene derivatives. Benzene according to the theory of resonance. Resonance: concept, formulas and limit ratio than chemical balance. Contribution of the formulas limit the hybrid description. Aromatic compounds, chemical-physical properties. monocyclic aromatic compounds, bicyclic and polycyclic. The dell'aromaticità criteria: the rule of Huckel. Examples of aromatic carbon and hetero-polycyclic systems. Reactivity of aromatic compounds. Electrophilic aromatic substitution reaction. Mechanism of electrophilic aromatic substitution reaction. The five important reactions: nitration, Sulphonation. Friedel-Crafts alkylation, Friedel-Crafts Acylation and Halogenation. Replace. Aromatic electrophilic of monosubstituted benzenes. electronic effect of substituents (substituents EWG and EDG): considerations of a second electrophilic substitution: activating, deactivating and exceptions. orientation effects in monosubstituted benzenes.
Phenols. Acidity of phenols Preparation of phenols. Ossidaz. of cumene. Reactivity of phenols. Reactions of substitution on the aromatic ring. oxidation reactions (quinones).
aromatic heterocyclic systems. Classification of aromatic heterocycles. Eteroaromaticità. elettronricchi systems: pentatomic heterocycles containing only one atom (furan, thiophene, pyrrole). pentatomic benzocondensati heterocycles containing only one heteroatom (benzopirrolo or indole). elettronpoveri systems: esatomici heterocycles with one heteroatom (pyridine) .Sistemi heterocyclic and their nomenclature depending on the size of the cycle and the number of heteroatoms present. condensed heterocyclic systems
Aldehydes and ketones. electronic structure of aldehydes and ketones. IUPAC Nomenclature of aldehydes and ketones. Preparation of aldehydes and ketones. Preparation of aldehydes and ketones from carboxylic acids and derivatives. Preparation of carboxylic acids. Preparation from chlorides of carboxylic acids. Preparation of esters. Preparation of amides. Reactivity of aldehydes and ketones. nucleophilic addition reaction to carbonyl double bond. Catalysis acid and base in the nucleophilic addition reactions to the carbonyl double bond. Comparison of reactivity between aldehydes and ketones. Stereochemistry of the nucleophilic addition reaction to carbonyl double bond. nucleophilic addition reactions. Carbon nucleophiles. Addition of hydrogen cyanide. Addition of organometallic compounds, of terminal alkynes, of carbanions: oxygen nucleophiles: addition of water, the alcohols: hemiacetals and cyclic hemiacetals. Nucleophilic sulfur. Addition of thiols. Nucleophilic nitrogen. Addition of ammonia and primary amines, ammonia derivatives. oxidation reactions. reduction reactions. Reduction to alcohols.
The amines. Aliphatic amines IUPAC Nomenclature of amines. primary amines. secondary amines tertiary amines. Quaternary ammonium salts. amino group as a substituent. Arylamines (aniline). Nitrogen electronic structure. Ammonia Reaction between ammonia and acids. Reactions of ammonia amines Properties. Basicity and nucleophilicity. Preparation of amines. direct alkylation. Amines via reduction reactions. Reduction of nitriles. Reduction of amides. Reaction with nitrous acid: the diazonium salts: Reaction of primary amines with nitrous acid. Reaction of secondary amines with nitrous acid. Reaction of tertiary aliphatic amines with nitrous acid. Reaction of aromatic amines with nitrous acid.
Carboxylic acids and their derivatives. electronic structure of carboxylic acids. IUPAC nomenclature of carboxylic acids. Acidity of carboxylic acids. Inductive effects in the aliphatic carboxylic acids. Dicarboxylic acids. Saturated and unsaturated fats. 3 acids and 6. Preparation of carboxylic acids: oxidative and hydrolytic methods. Reactivity of carboxylic acids. electronic structure and IUPAC nomenclature of acid chlorides. Preparation and reactivity of acid chlorides. The anhydrides. electronic structure and IUPAC Nomenclature for Foreign. Preparation and reactivity of Foreign. Fischer esterification. basic hydrolysis of an ester. Lipids: the "fat" (triglycerides, glycerophospholipids). Saponification reaction. The soaps. Oils and waxes. Hydrogenated fats. Preparation of an ester by acyl chloride. The lactones. The thioesters. electronic structure and IUPAC nomenclature of amides. chemical-physical properties of the amides. Preparation and reactivity of amides. Hydrolysis of amides. Preparation and reactivity of nitriles. Reactions of reduction of carboxylic acids and derivatives. Reduction in foreign to primary alcohols. Reduction of amides to amines. Sulfonic acids.
Enols, enolate anions. Acidity of hydrogens in to the carbonyl group. Unsaturated aldehydes and ketones . Reactivity of enolate anions. Alkylation reactions.
Carbohydrates. Definition, Background. Classification of carbohydrates. Monosaccharides, oligosaccharides and polysaccharides. Aldoses. Ketosis Fischer Convention. Series steric and relative IUPAC nomenclature. Construction from synthesis Kiliani-Fischer from D-glyceraldehyde in the series of D-aldoses. Acronyms. The family of D-ketosis. The mutarotation and poor glucose reducing power. anomeric form. cyclic structures of monosaccharides. Haworth formula. furanosidiche and piranosidiche structures. Anomeric configuration and . Definition of anomers. The epimers. conformational structure. Carbohydrate oxidation: Tollens test, Fehling's reagent; types of sugar acids. Reduction of carbohydrates: sugars alcohol. Amino sugars. Deossicomposti. Glycosides: glycoside bond and diglicosidico. Disaccharides: nomenclature and properties. Sucrose and sweeteners. Lactose, maltose and cellobiose. Polysaccharides: starch, cellulose, chitin, pectin, cellulose, glycogen.
The nitrogenous bases in DNA and RNA. Nucleosides and nucleotides. Examples
Amino acids, peptides and proteins. Amino acids. Definition and classes. Structure of proteinogenic amino acids. natural amino acids not Proteinogenic. Polarity and classification of amino acids. acid-base properties of amino acids. The isoelectric point, definition, values. Electrophoresis. Peptides. peptide bond: formation and properties. Conventions. Peptides of biological interest. Structure of proteins. Determination of the primary structure of peptides and proteins (eg human insulin). Determination of amino acid composition. Identification of amino acid N-terminal amino acid C-terminal identification. secondary, tertiary and quaternary structure of proteins (eg, albumin, hemoglobin). Proteins such as enzymes. Properties, definitions: apoenzyme, holoenzyme. The major cofactors.
Alpha-substitutions and condensations of the carbonyl compounds. The keto-enolica- Alfa halogenation of ketones and acids carbossilici- Condensation aldolica- aldol condensations incrociate- The Claisen-condensation reactions of beta-dicarbonilici- compounds The reaction of Michael-
Terpenes, history, classification of Ruzicka: emiterpeni, monoterpenes, sesquiterpenes, diterpenes, tri- and tetraterpenes. acyclic and cyclic monoterpenes. Examples of geraniol and nerol. biological precursors of terpenes: dimetilallilpirofosfato and isopentenilpirofosfato. Genesis of higher terpenes (diagram and related precursors). Examples of classes of emiterpeni (pheromones), acyclic and cyclic monoterpenes, carotenoids (lycopene, carotenes). The class C30: steroids. Animal sterols (lanosterol, cholesterol) and plant (stigmasterol and ergosterol). The importance of cholesterol (HDL, LDL, total cholesterol, risk index). of cholesterol metabolism products. Signs to cardiac glycosides, male sex hormones, female and progestagens.