CODE 65100 ACADEMIC YEAR 2016/2017 CREDITS 8 cfu anno 1 CHIMICA E TECNOLOGIE CHIMICHE 8757 (L-27) - SCIENTIFIC DISCIPLINARY SECTOR CHIM/06 TEACHING LOCATION SEMESTER 2° Semester PREREQUISITES Propedeuticità in ingresso Per sostenere l'esame di questo insegnamento è necessario aver sostenuto i seguenti esami: Chemistry and Chemical Technologies 8757 (coorte 2016/2017) GENERAL AND INORGANIC CHEMISTRY 65096 2016 Propedeuticità in uscita Questo insegnamento è propedeutico per gli insegnamenti: Chemistry and Chemical Technologies 8757 (coorte 2016/2017) BIOLOGICAL CHEMISTRY 25727 Chemistry and Chemical Technologies 8757 (coorte 2016/2017) LABORATORY OF ORGANIC CHEMISTRY 65111 Chemistry and Chemical Technologies 8757 (coorte 2016/2017) ORGANIC CHEMISTRY 2 65113 AIMS AND CONTENT LEARNING OUTCOMES The students will be provided with the fundamental notions of organic chemistry. First some basic concepts on atomic and molecular orbitals, chemical bonds, shape of the molecules, acid and bases, will be given. Then, the structure, nomenclature, synthesis and reactivity of the main classes of functional groups (aliphatic and aromatic hydrocarbons, alkyl and aryl halogen derivatives, alcohols and thiols, phenols, ethers, amines, aldehydes, ketones, carboxylic acids and their derivatives) will be described, not overlooking the stereochemical aspects. TEACHING METHODS Traditional lessons in the classroom (64 hours). The solutions of problems will be treated in additional and optional tutoring hours. The attendance is not compulsory but, for statistical means, it wil be anyway monitored. SYLLABUS/CONTENT Introduction to organic chemistry Chemodiversity in organic chemistry. Lewis formulas. Representation of molecules. VSEPR theory. Molecular orbitals. Tridimensional structure. Alkanes and cycloalkanes. Constitutional isomers The concept of functional group Survey of the main functional classes and basic systematic nomenclature Physico-chemical properties of organic compounds Acid-base properties (Bronsted) of organic compounds Stereochemistry and conformational equilibria of organic molecules Generality on organic reactions: names of main reactions, thermodynamical and kinetic aspects Electrophilic addition to C=C bonds Generality and Markovnikov rule. Hammond postulate Addition of hydrogen halides, water, halogens, boranes, formation of bromohydrins Reactions of dienes and alkynes Aromatic compounds benzene and aromaticity aromatic electrophilic substitutions: halogenation, nitration, solfonation, Friedel-Crafts acylations and alkylations steric and electronic effects of substituents. Orientation of electrophilic substitutions on monosubstituted benzenes. naphthalene: properties and electrophilic substitutions Heteroaromatic compounds. Basic properties. Tautomeric equilibria. The reactions of C=O bonds Reversible nucleophilic additions to carbonyl compounds: gem-diols, acetals, imines Generality of acylic nucleophilic substitutions Preparation and hydrolysis of: acyl chlorides, anhydrides, esters, amides, nitriles Acyl derivatives of other oxyacids: arbonic acid, sulphonic acids, nitric acid, sulphuric acid, phosphoric acid Redox reactions in organic chemistry formal hydrogenations and dehydrogenations involving redox at C atom hydrogenation of alkenes and alkynes oxidation of oxygenated functionalities reduction of oxygenated functionalities reductive amination other redox reactions at C atom monooxygenation of hydrocarbons epoxidation dihydroxylation ozonolysis redox reactions involving N and S. Nomenclature and properties of sulphur derivatives. oxidative additions of halides to metals: Grignard and organolithium reagents Formation of C-C bonds Reactions of Grignard and organolithium reagents with carbonyl and acyl derivatives Acidity at the alpha position: aldol and Claisen reactions Aliphatic Nucleophilic Substitutions SN2 reactions: generality and application to th synthesis of ethers, amines, and to enolate alkylations E2 elimination SN reaction E1 elimination Reactivity of epoxides with nucleophiles Terpene biosynthesis Other reactions of aromatic compounds aromatic nucleophilic substitution: SNAr mechanism, benzyne, SN1 Diazonium salts. Diazocopulation radical reactions Generality radical polymerization of ethylene and styrene halogenation of alkanes phenol synthesis via cumene hydroperoxide auto-oxidation. Radical inhibitors quinones and hydroquinones RECOMMENDED READING/BIBLIOGRAPHY The program will not follow a specific book. Anyway, students are advised to integrate the lessons with consultation of any Organic Chemistry book for chemists (that can be borrowed in the library). For example: Jonathan Clayden, Nick Greeves, Stuart Warren, Peter Wothers, Fondamenti di Chimica Organica, Zanichelli Brown-Foote, CHIMICA ORGANICA, Edises J. McMurry, CHIMICA ORGANICA, Piccin A.A. varii, CHIMICA ORGANICA (a cura di B. Botta), ediermes Yurkanis Bruice, CHIMICA ORGANICA, EdiSES TEACHERS AND EXAM BOARD LUCA BANFI Ricevimento: Luca Banfi is always present in the department from 8.30 to 13.00 and from 15.00 to 18.30. However, due to the many lessons and exams he is involved in and to the institutional meetings, it is impossible to establish in advance a time interval where he will be surely not engaged. Therefore students are pleased to take an appointment in advance by E-mail. They will be received in few days. Exam Board LUCA BANFI (President) ANDREA BASSO CHIARA LAMBRUSCHINI LISA MONI RENATA RIVA SERGIO THEA LESSONS LESSONS START From february, 20, 2017 (according to the timetable that will be reported on www.ctc.unige.it). Class schedule ORGANIC CHEMISTRY EXAMS EXAM DESCRIPTION The students who want to be submitted to the exam must registrate at least 48 hours in advance on https://servizionline.unige.it/studenti/esami/prenotazione The exam will be essentially oral. However, it will be preceded, on the same day, by a written exam, whose aim is just to filter off the unprepared students in order to avoid useless loss of time for both sides. Therefore the written exam will not involve solution of problems, it will be relatively easy, and onlt these four outcomes will be communicated few hours after its end: excellent, good, sufficient and not sufficient. Only the students who have gained the first three grades will be admitted to the oral exam. The grade obtained during the written exam will not count for the final grade, apart from the fact that the maximum available grade for those judged "sufficient" will be 26. Even the students who have got "excellent" may eventually fail the oral exam. The oral exam will involve 3 questions. The first one will be quite general and will be taken from a list that will be made public, during the course, through the "aulaweb" service. The second and third will be more specific. The relative weight of the three questions will be, approximately, 50%, 25%, 25%. When students who have got "excellent" in the wrtten exam, answers very well to the first question, the commission may decide to stop the exam (with a grade of 30) or to pose a more difficult question in order to judge if the student is worth the "cum laude". During the oral exam the student must demonstrate to have reached the learning outcomes, both orally and (most importantly) writing formulas, chemical equations, mechanisms. In case of students who have certified a "specific learning disease" (DSA) the commission may decide to go directly thrpough the oral exam where the student will be given enough time to understand the questions and answer to them. Requests of these aids must be presented not directly to the professor, but to the reference persons for DSA at the School of Science. When the commission will judge that the learning oucomes have not been reached, the students willbe invited to repeat the exam in one of the subsequent dates. When the commission have decided for a positive grade, the student may ask to refuse ot and repeat the exam. However the commission will decide whether to accept or not this refusal. In any case the request of refusal must be presented at once, and students are not allowed to change their minds later. If, later,the students repeats the exam and obtain an inferior grade, he/she can not ask to receive the grade that he/she had preiously refused. ASSESSMENT METHODS The oral exam is always carried out by two teachers with at least 5 years of experience and will last at least 30 minutes. In this way, taking into account also the preliminary written exam, the commission is definitely able to verify with high accuracy if the student has reached or not the learning outcomes. During the oral exam the student must demonstrate to have reached the learning outcomes, both orally and (most importantly) writing formulas, chemical equations, mechanisms. When the commission will judge that the learning oucomes have not been reached, the students willbe invited to repeat the exam in one of the subsequent dates. Exam schedule Data appello Orario Luogo Degree type Note 28/06/2017 09:00 GENOVA Scritto 12/07/2017 09:00 GENOVA Scritto 27/07/2017 09:00 GENOVA Scritto 04/09/2017 09:00 GENOVA Scritto 19/09/2017 09:00 GENOVA Scritto 17/11/2017 09:00 GENOVA Scritto + Orale 08/01/2018 09:00 GENOVA Scritto + Orale 22/01/2018 09:00 GENOVA Scritto + Orale FURTHER INFORMATION Only the students who have already successfully obtained the credits for "General Chemistry and Laboratory" will be admitted to the exam.
