Ateneo - UPO

Alcohols and ethers
Aldehydes e ketones
Aromatic hydrocarbons
Carboxylic acids
Aliphatic and aromatic amines
Aromatic aldehyides
Phenols
Outline on main sulfur containing compounds

Structure, nomenclature and properties of the main penta- and hexacyclic etherocyclic systems
Functionalization of electron-rich and electron-poor heterocyclic systems
Synthetic entries into the main heterocyclic systems and their products of benzo-condensation

N. E. Shore, P. Vollhardt, Chimica organica, Zanichelli
W.H. Brown, C.S. Foote, Chimica organica, Edises
J. McMurry, Chimica organica, Piccin
Broggini-Zecchi. La Chimica degli Eterocicli. La Scientifica, 2009 (paperback/e-Book)

D’Auria et al.. Guida Ragionata allo Svolgimento degli Esercizi di Chimica Organica. Loghia

Additional textbook
R. Norman, J.M. Coxon, Principi di sintesi organica, Ed. Piccin

Knowledge of the reactivity of the main functional groups of organic molecules, with emphasis on reaction mechanisms, also with links to biological examples to exemplify the prerequisites to other disciplines. Introduction of the basic concepts of organic synthesis, to prepare the student to the construction of even polyfunctional molecules. Applications of these concepts to the chemistry of heterocycles. Development of an adequate self-learning ability. Ability to apply their knowledge, understanding, and ability to solve problems to new or unfamiliar issues, inserted in a more general (or interdisciplinary) context.

Knowledge of the structure and properties of the main functional groups of organic compounds. Ability to manage the resonance formulas and concepts of acidity and basicity in organic chemistry.

Lectures with multimedia support and exercises. In particular, the use of concepts in facing specific problems will be shown in order to provide a problem-solving ability.

Supporting material for the course will be added to the DIR platform

The exam will take place orally with the request for the synthesis of a polyfunctional molecule, with consequent discussion of synthetic and mechanistic aspects, with particular attention to the ability to establish logical connections between different topics. The oral exam will include both the organic chemistry and the chemistry of heterocyclic compounds.

Alcohols: nomenclature and properties. Preparation and reactivity. Cromium oxidations (Jones, CrO3-pyridine, PDC, PCC) Swern oxidation. Diols. Degradation with periodate and permanganate. Pinacolinic trasposition, mechanism and stereochemistry.Substitutions of the hydroxyl group with halogens. Sulfonates. Lithium, magnesium and copper (mention) organometallic reagents: comparison of reactivity.
Ethers: nomenclature and properties. Preparation and reactivity.
Aldehydes and ketons: nomenclature and properties. Preparation and carbonyl reactivity. Keto-enol tautomerism. Acyl nucleophilic addition reactions: addition of organometallic compounds, hydrides, HCN, alcohols ammonia derivatives. Bayer-Villiger reaction. Mention to the concept of protecting groups. Acetals as protecting groups. Wittig reaction. Enolate ions. Mechanism of base and acid catalyzed ketones halogenation. Aldol condensation with mention to stereochemical aspects.
Aromatic hydrocarbons. Aromaticity. Huckel rule. Omoaromatic and structures of main heterocyclic compounds. Aromatic ions.
Electrophilic aromatic substitution: nitration, sulfonation, Halogenation, Friedel-Crafts alkylation and acylation, chloromethylation reaction. Mechanism and substituent effect on reactivity and orientation. Electrophilic substitution on polycyclic aromatic compounds.
Nucleophilic aromatic substitution. Mechanisms of addition-elimination and elimination-addition.
Carboxylic acids: acyl halides, esters and amides. Nucleophilic acyl substitution reactions. Mechanisms of basic and acid hydrolysis of esters. Hofmann transposition of amides. Hell-Vohlard-Zelinsky.
Dicarboxylic acids; alkylation of malonates and acetacetates. Ketoacids and ketoesters; Claisen and Dieckmann condensation acid and basic cleavage and keto-enol tautomerism.. Claisen reaction. Perkin condensation. Oxyacids. Reformatsky reaction. Mannich condensation. -Unsaturated carbonyl compounds: Preparation and reactivity. Michael reaction and Robinson annulation. Mention to aliphatic nitroderivatives.
Aliphatic and aromatic amines: basicity and preparations. Reactivity: quaternari ammonium salts and Hofmann degradation, amides and sulfonamides, Hinsberg test, reaction with nitrous acid. Diazonium salts: formation and reactivity. Azo-, azoxi e idrazoderivatives.
Aromatic aldehyides: formylation reactions (Gattermann, Gattermann-Koch, Vielsmeier).
Phenols: acidity and preparations. Reactivity. Fries transposition. Kolbe and Reimer-Tiemann reaction. Quinones.
Mention on main sulfur containing compounds: Thiols, thiophenols, sulfides, sulfoxides, sulfones, sulfenic, sulfynic and sulfonic acids, sulfonyl chlorides and sulfonamides.

Structure and properties of the main heterocycles systems (nomenclature, aromaticity, tautomerism, acid-base properties)
General synthetic methods for heterocyclic compounds.
Survey of the major electron-rich (pyrrole, furan, thiophene, 1,2-azoles, 1,3-azoles and their products of benzo-condensation) and electron-poor systems (pyridine, pyrilium ion and their benzo-condensed products.

The student has to demonstrate an adequate knowledge and understanding of the topics developed during the course, with particular focus on the proper understanding of the logic of organic chemistry. It is expected the student to be able to apply knowledge and understanding in dealing with even complex problems with sufficient personal good sense.