OVERVIEW

Teaching of Organic Chemistry I for the Course in CTF held by Dr. Silvana Alfei, a confirmed researcher of DIFAR's Organic Chemistry Group (SSD CHIM / 06). The course is in the first semester of each a.c from the first useful day according to the didactic calendar until the last useful day and according to the timetable decided by the Timetable Committee. In the case of missed lessons for any reason (including holidays) is the use of the teacher to retrieve them.

AIMS AND CONTENT

LEARNING OUTCOMES

The course aims to provide logical and systemic tools, curating their learning, to enable everyone concerned to achieve good knowledge of structure, physical characteristics, reactivity, mechanistic action, synthesis of the main functional groups of organic chemistry as a basis for all the future studies and their theoretical and applicative insights.

AIMS AND LEARNING OUTCOMES

The course aims to describe the fundamental principles of Organic Chemistry by facilitating its study with the introduction of electronic theories and the continuous application of their concepts, in order to give the matter some consistency. Without these assumptions, Organic Chemistry may appear to be a non-homogeneous set of methods and reactions to be learned in a mnemonic manner.The main knowledge will cover:- the general aspects and the foundations of reactivity- the characteristics of the main functional groups- the stereochemistry, that is, the three-dimensional aspects that can characterize an organic molecule- the bases for describing the mechanism of a reaction.The main skills (ie the ability to apply acquired knowledge) will be:-identifies how a functional group can react-use the knowledge gained to propose the synthesis of an organic molecule

TEACHING METHODS

The lesson consists of 3 weekly lessons of 2 hours each, during which all the notions of the course are given to the students by using slides organized by the teacher. The complete slides that cover the whole course program are provided to students since the first day of lessons and are sufficient for comprehensive preparation. However, support texts and exercises are recommended. One day a week, however, the lesson is turned on the blackboard to accustom the student to the design of molecules and reactive schemes. Lessons are also supplemented with exercises.Furthermore the last part of the course (about 1 month) is devoted exclusively to exercises and simulations.

SYLLABUS/CONTENT

Spatial organization of organic molecules. The carbon. Structural, optical and conformational isomerism. Fischer Projections. Racemic mixtures. Newman Projections. Alcanes: radical alogenation and preparations. Alicyclic hydrocarbons: stability of cycloalcans. Cyclopropane preparations. Alchenes: the double ethylene bond. Geometric isomerism. Electrophilic and nucleophilic reagents. Reactions: catalytic hydrogenation; Addition of HX, X2, HClO, HBrO, H2SO4, H2O. Markovnikov rule and carbocations. Isomerization of olefins. Oximercuratin-demercuration. Hydroboration-oxidation. HBr anti-Markovnikov addition. Allylated alogenation. Oxidation. Oxidative scissions. Preparations. Alchine: the triple acetylene bond. Acidity of acetylene hydrogen; Formation of metal derivatives. Reactions: alchine reductions to cis or trans alchenes or to alcanes; Addition of X2, HX, H2O. Preparations. Polyenes isolated, conjugated, accumulated. Cumulenes. Resonance in conjugated dienes. Electrophilic addition to conjugated dienes. Aromatic hydrocarbons. Benzene: aromatic electrophilic replacement reactions. Inflence of substituents and orientation. Mesomeric and Inductive Effect. Substituents Classification. Arenas: preparations and reactions. Alkyl halides: SN2, SN1, E2, E1 reactions. Reactions with metals. Reductions. Preparations. Vinyl halides: electrophilic addition reactions, dehydrohalogenation, magnesium reaction; Inertia towards replacements. Preparations. Aryl halides: aromatic nucleophilic substitution reactions (addition-elimination, elimination-addition); Reaction with magnesium and lithium alkyl. Preparations. Alcohols: Hydrogen bonds. Acid-base properties. Formation of salts and ethers. Reactions: oxidation, dehydration, transformation in alkyl halides. Eliminations and substitutions. Preparations. Phenols: acid-base properties. Formation of ethers. Reactions by Kolbe and Raimer-Tiemann. Preparations. Ether: acid cleavage. Basic Properties. Trialchiloxonium salts. Synthesis of Williamson. Preparations. Epoxides: catalyzed addition of water, HX, alcohols, ammonia, amines, HCN, Grignard, metal hydrides. Preparation: olefin oxidation, dehydrohalogenation of aloidrines. Organometallic compounds: reactivity. Preparations of lithium, magnesium, zinc, cadmium organometallics. Grignard: reactions with acids, water, oxygen, halogens, carbon dioxide, carbonyl compounds, esters, acyl chlorides, epoxies, disubstituted amides, nitriles. Secondary reactions. Cadmium-organic and lithium dialkyl cuprate: reactions. Reformatsky. Aldehydes and ketones: the carbon-oxygen bond. Reactions: catalytic reduction; Clemmensen's reduction. Oxidation of aldehydes. Nucleophilic additions to carbonyl. Reductive amination; Reduction by Wolff-Kishner; Cannizzaro's reaction. Hydrogen acidity in alpha to carbonyl. Enolization. Carbanions-enol-anion. Acid or base catalyzed Alfa halogenation. Aloform reaction. Aldol condensation. Wittig's reaction. Preparations. Oxidation of Oppenauer and reduction of Meerwein-Pondorf-Oppenauer-Verley. Carbenes. Carboxylic acids: acidity; Salt formation. Reduction with lithium aluminum hydride. Formation of acyl halides. Hell-Volhard-Zelinsky. Acyl derivatives. The acyl function. Substitution of acyl nucleophile. Fischer Esterification. Reactions with Grignard and lithium aluminum hydride. Acyl halides and carboxylates, cadmium-organic compounds and dialkylated lithium. Reductions of acyl halides. Claisen condensation. Nitrile synthesis, malonic synthesis. Acetoacetic synthesis. Nitriles: Catalytic addition of water and alcohols, reduction of imines and amines, Reactions with Grignard. Acidity of hydrogen in alpha at CN. Acetonitrile alkylation. Nitrile preparations. Amin: nitrogen stereochemistry, acid-base properties. Reactions with: alkaline metals, Grignard, acyl halides, anhydrides, alkyl halides, carbonyl compounds, nitrous acid. Amine preparations: Gabriel synthesis, degradation of Hofmann, Curtius, Schmidt. Methylation of Eschweiler-Clarke. Diabetic salts: structure and stability. Replacement reactions of nitrogen with -Cl, -Br, -CN, -I, -F, -OH, -H and of copulation. Diazomethane: structure. Reactions with: inorganic acids, carboxylic acids, mobile hydrogen compounds, acyl chlorides. Arndt-Eistert's reaction. Preparation. Amino acids: structure, nomenclature, peptide bond.

RECOMMENDED READING/BIBLIOGRAPHY

John McMurry, CHIMICA ORGANICA, Ed. Piccin

Paula Yurkains Bruice, CHIMICA ORGANICA, Ed. EdiSES

Botta et all, CHIMICA ORGANICA, Ed. Edi-Ermes

Solomons Fryhle, CHIMICA ORGANICA, Ed. Zanichelli

Brown, CHIMICA ORGANICA, Ed. EdiSES

Fessenden & Fessenden, CHIMICA ORGANICA, Ed. Piccin

M.V. D’Auria, O.T. Scafati, A. Zampella, GUIDA RAGIONATA allo SVOGIMENTO di ESERCIZI di CHIMICA ORGANICA, Ed. Loghia

TEACHERS AND EXAM BOARD

Exam Board

SILVANA ALFEI (President)

FRANCESCO LUCCHESINI

PAOLO OLIVERI

LESSONS

LESSONS START

End of September 2016: the first useful day according to the didactic calendar, except for unforeseen.

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

A Written test composed of five exercises to which a score is associated to reach the maximum score of 30. Access to oral exam is precluded to candidates who do not qualify for the sufficiency with the minimum score of 18.

ASSESSMENT METHODS

The exam consists of two parts that take place on the same day: the first part involves a written test consisting of 5 questions on the topics taught in lessons (duration 60-90 minutes); The second part (only for students who have reached the minimum score of 18 in the script) consists of an oral exam that, starting from the discussion of the answers delivered by the student in the written test, intends to acquire a more comprehensive and complete picture of the candidate's preparation (duration 40 Minutes). No tests “in itinere” are given. No pre-appeals or post-appeals or extraordinary appeals are granted.

Exam schedule