CODE 60822 ACADEMIC YEAR 2023/2024 CREDITS 8 cfu anno 2 CHIMICA E TECNOLOGIA FARMACEUTICHE 8451 (LM-13) - GENOVA SCIENTIFIC DISCIPLINARY SECTOR CHIM/06 TEACHING LOCATION GENOVA SEMESTER 1° Semester PREREQUISITES Propedeuticità in ingresso Per sostenere l'esame di questo insegnamento è necessario aver sostenuto i seguenti esami: Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) GENERAL AND INORGANIC CHEMISTRY (PCT)(MD) 55401 2022 Propedeuticità in uscita Questo insegnamento è propedeutico per gli insegnamenti: Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) FOOD CHEMISTRY 64194 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) DRUGS ANALYSIS II 80445 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) PHARMACEUTICAL AND TOXICOLOGICAL CHEMISTRY II (PCT) 67558 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) INSTRUMENTAL ANALYSIS OF DRUGS (WITH PRACTICE) 80452 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) PLANT BIOLOGY AND BIOACTIVE COMPOUNDS (I.C.)(PCT MD) 80447 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) BIOCHEMISTRY AND APPLIED BIOCHEMISTRY (I.C.)(PCT MD) 80520 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) PHYSICS METHODS IN ORGANIC CHEMISTRY (MD) 64193 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) ORGANIC CHEMISTRY II (PCT)(MD) 60828 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) PHARMACEUTICAL TECHNOLOGY AND LAW I (PCT) 67569 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) PHARMACOLOGY AND PHARMACOTHERAPY (PCT) 67563 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) GENERAL PHARMACOLOGY AND TOXICOLOGY (PCT MD) 64200 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) PHARMACEUTICAL TECHNOLOGY AND LAW II (WITH PRACTICE9 (PCT MD) 67615 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) APPLIED MEDICINAL CHEMISTRY (MD) 67617 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) COSMETIC PRODUCTS 67501 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) DRUG SYNTHESIS (WITH PRACTICE) 80453 Pharmaceutical chemistry and technology 8451 (coorte 2022/2023) MEDICINAL AND TOXICOLOGICAL CHEMISTRY I 80446 TEACHING MATERIALS AULAWEB OVERVIEW The course concerns the teaching of Organic Chemistry I for the CTF Degree Course, held by Prof. Silvana Alfei of the DIFAR Organic Chemistry group (SSD CHIM / 06). The purpose of the course is to provide students with the elements of Organic Chemistry necessary to successfully tackle subsequent subjects (Organic Chemistry II) including professionalizing ones such as Pharmaceutical Chemistry I and II, and those for which practical laboratories are provided. AIMS AND CONTENT LEARNING OUTCOMES As part of the need to give students a robust foundation in Organic Chemistry, in order to be able to face the subsequent Organic Chemistry II course, the program carried out includes notions of nomenclature of the main organic molecules, notions concerning the chemistry of the main functional groups and systems aromatics, and notions concerning nomenclature and structure of the 20 natural amino acids. An essentially mechanistic approach is followed for the rationalization of the experimental results described. AIMS AND LEARNING OUTCOMES The course aims to provide logical and systemic tools, taking care of their learning, to allow all attending students to achieve a good knowledge of structure, physical characteristics, reactivity, mechanistic action, synthesis of the main functional groups of organic chemistry as a basis for all future studies in the sector and their theoretical and applicative insights. The course aims to describe the fundamental principles of Organic Chemistry facilitating their study with the introduction of electronic theories and the continuous application of their concepts, in order to give the subject a certain coherence. Without these assumptions, in fact, Organic Chemistry can appear as a non-homogeneous set of methods and reactions to be learned in a mnemonic way. The main knowledge will concern: - the general aspects and foundations of reactivity - the characteristics of the main functional groups - stereochemistry, that is the three-dimensional aspects that can characterize an organic molecule - the basis for describing the mechanism of a reaction. The main skills (i.e. the ability to apply the knowledge acquired) will be: - identify the way in which a functional group can react - use the acquired knowledge to propose the synthesis of an organic molecule PREREQUISITES Passing the preparatory exam in General and Inorganic Chemistry. TEACHING METHODS The course includes 3 weekly lectures of 2 hours each during which all the notions concerning the program of the CTF Course are transmitted to the students in detail using slides organized by the teacher himself. The complete slides that cover the entire program of the course are provided to students from the first day of class and are sufficient for an exhaustive preparation. However, supporting texts and exercises are highly recommended. Most of the lessons are held on the blackboard to accustom the student to drawing molecules and reactive patterns. The lessons are also supplemented with exercises and examples on a topic-by-topic basis. The last part of the course (after the Christmas break) is instead dedicated exclusively to exercises and simulations. SYLLABUS/CONTENT Spatial organization of organic molecules. Carbon. Structural, optical and conformational isomerism. Fischer projections. Racemic mixtures. Newman projections. Alkanes: radical halogenations and preparations. Alicyclic hydrocarbons: stability of cycloalkanes. Preparations of cyclopropanes. Alkenes: the ethylene double bond. Geometric isomerism. Electrophilic and nucleophilic reagents. Reactions: catalytic hydrogenation; addition of HX, X2, HClO, HBrO, H2SO4, H2O. Markovnikov's rule and carbocations. Isomerization of olefins. Oxymercuriation-demercuriation. Hydroboration-oxidation. HBr's anti-Markovnikov addition. Allyl halogenation. Oxidations. Oxidative cleavages. Preparations. Alkynes: the triple acetylene bond. Acidity of acetylene hydrogen; formation of metal derivatives. Reactions: reductions to alkanes and to cis or trans alkenes; addition of X2, HX, H2O. Preparations. Structure of isolated, conjugated and accumulated dienes. The cumulens. Resonance in conjugated dienes. Aromatic hydrocarbons. Benzene: aromatic electrophilic substitution reactions. Orienting influence of substituents. Mesomeric and inductive effect. Classification of substituents. The arenas: preparations and reactions. Alkyl halides: SN2, SN1, E2, E1 reactions. Reactions with metals. Reduction to alkanes. Preparations. Vinyl halides: electrophilic addition reactions, dehydrohalogenation, reaction with magnesium; inertia towards substitutions. Preparations. Aryl halides: aromatic nucleophilic substitution reactions (addition-elimination, elimination-addition); reaction with magnesium and lithium alkyls. Preparations. Alcohols: hydrogen bonds. Acid-base properties. Formation of salts and ethers. Reactions: oxidation, dehydration, transformation into alkyl halides. Eliminations and replacements. Preparations. Phenols: acid-base properties. Formation of ethers. Kolbe and Raimer-Tiemann reactions. Preparations. Ethers: acid splitting. Basic properties. Trialkyloxonium salts. Williamson synthesis. Preparations. Epoxides: addition of HX catalyzed water, alcohols, ammonia, amines, HCN, Grignard, metal hydrides. Preparations: oxidation of olefins, dehydrohalogenation of halohydrins. Organometallic compounds: reactivity. Preparations of organometals of lithium, magnesium, zinc, cadmium. Grignard: reactions with acids, water, oxygen, halogens, carbon dioxide, carbonyl compounds, esters, acid chlorides, epoxides, disubstituted amides, nitriles. Secondary reactions. Organic cadmium and lithium dialkylcuprates: reactions. Reformatsky. Aldehydes and ketones: the carbon-oxygen bond. Reactions: catalytic reduction; Clemmensen reduction. Oxidation of aldehydes. Nucleophilic addition to the carbonyl. Reductive amination; Wolff-Kishner reduction; Cannizzaro reaction. Acidity of hydrogens in alpha to carbonyl. Enolization. Carbanions-enolanions. Catalyzed alpha halogenation. Haloform reaction. Introduction to aldol condensation. Wittig reaction. Preparations. Oppenauer oxidation and Meerwein-Pondorf-Oppenauer-Verley reduction. Carbeni. Carboxylic acids: acidity; salt formation. Reduction with lithium aluminum hydride. Formation of acyl halides. Hell-Volhard-Zelinsky reaction: reaction equation and products. Acyl derivatives. The acyl function. Nucleophilic acyl substitution. Fischer esterification. Reactions with Grignard and lithium aluminum hydride. Acyl and carboxylated halides, organic cadmium compounds and lithium dialkylcuprates. Reductions of acyl halides. Claisen condensation. Nitrile synthesis, malonic synthesis. Acetoacetic synthesis. Nitriles: catalyzed addition of water and alcohols, reduction to imines and amines, Reactions with Grignard. Acidity of hydrogens in alpha to CN. Alkylation of acetonitrile. Preparations of nitriles. Amines: stereochemistry of nitrogen, acid-base properties. Reactions with: alkali metals, Grignard, acyl halides, anhydrides, alkyl halides, carbonyl compounds, nitrous acid. Amine preparations: Gabriel synthesis, Hofmann, Curtius, Schmidt degradation. Eschweiler-Clarke methylation. Salts of diazonium: structure and stability. Nitrogen replacement reactions with -Cl, -Br, -CN, -I, -F, -OH, -H and copulation. Diazomethane: structure. Reactions with: inorganic, carboxylic acids, mobile hydrogen compounds, acyl chlorides. Arndt-Eistert reaction. Preparation. Introduction to amino acids generic structure and configuration of natural alpha amino acids. RECOMMENDED READING/BIBLIOGRAPHY R. T. MORRISON, R. N. BOYD "ORGANIC CHEMISTRY" (Ambrosiana Publishing House) M. LOUBON "ORGANIC CHEMISTRY" (EdiSES) John McMurry, ORGANIC CHEMISTRY, Ed. Piccin Paula Yurkains Bruice, ORGANIC CHEMISTRY, Ed. EdiSES Botta et all, ORGANIC CHEMISTRY, Edi-Ermes Ed Solomons Fryhle, ORGANIC CHEMISTRY, Ed. Zanichelli Brown, ORGANIC CHEMISTRY, Ed. EdiSES Fessenden & Fessenden, ORGANIC CHEMISTRY, Ed. Piccin M.V. D'Auria, O.T. Scafati, A. Zampella, REASONED GUIDE to LEISURE EXERCISES of ORGANIC CHEMISTRY, Ed. Loghia Any other texts will be communicated to students year by year at the beginning of the course. Texts that the student had available are evaluated by the teacher for their suitability at the beginning of the course. TEACHERS AND EXAM BOARD SILVANA ALFEI Ricevimento: The day dedicated to receptions is Friday from 11.00 onwards by appointment. However, meetings with students and / or undergraduates can be arranged from time to time according to the needs and requirements of the students themselves and upon request both during the entire period of the course and beyond. Exam Board SILVANA ALFEI (President) OMAR GINOBLE PANDOLI ANDREA BASSO (Substitute) GUENDALINA ZUCCARI (Substitute) LESSONS LESSONS START End of September: first useful day according to the didactic calendar, barring unforeseen events. Class schedule The timetable for this course is available here: Portale EasyAcademy EXAMS EXAM DESCRIPTION Written assignment in preparation for the oral question. ASSESSMENT METHODS The assessment of the knowledge acquired by the students will take place only during the scheduled exam sessions. No ongoing tests will be carried out. Exam schedule Data appello Orario Luogo Degree type Note 17/06/2024 11:00 GENOVA Scritto 08/07/2024 11:00 GENOVA Scritto 16/09/2024 11:00 GENOVA Scritto 03/02/2025 11:00 GENOVA Scritto 17/02/2025 11:00 GENOVA Scritto