Organska kemija I

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UČNI NAČRT PREDMETA / COURSE SYLLABUS Predmet: ORGANSKA KEMIJA 1 Course Title: ORGANIC CHEMISTRY 1 Študijski program in stopnja Študijska smer Letnik Semester Study Programme and Level Study Field Academic Year Semester VSŠP Kemijska tehnologija, 1. stopnja / 1. 2. st
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PSP Chemical Technology, 1 Cycle / 1 2nd Vrsta predmeta / Course Type: obvezni / Mandatory Univerzitetna koda predmeta / University Course Code: KT108 Samost. delo Predavanja Seminar Vaje Klinične vaje Druge oblike Individual ECTS Lectures Seminar Tutorial Work študija Work 60 15 / / / 75 5 Nosilec predmeta / Lecturer: doc. dr. Bogdan Štefane / Dr. Bogdan Štefane, Assistant Professor Jeziki / Languages: Predavanja / Lectures: slovenski / Slovenian Vaje / Tutorial: slovenski / Slovenian Pogoji za vključitev v delo oz. za opravljanje Prerequisites: študijskih obveznosti: Študent oz. kandidat mora imeti predmet The course has to be assigned to the student. opredeljen kot študijsko obveznost. Vsebina: Content (Syllabus outline): Nomenklatura (poimenovanje) organskih spojin. Nomenclature of organic compounds. Structure and bonding of organic compounds; acids and Struktura in vezi v organskih spojinah, kislost in bases. The nature of chemical bonds, bond bazičnost. Narava kemijske vezi, vezna entalpija, (dissociation) enthalpy, hybridization, ionic and hibridizacija, ionske in kovalentne vezi; struktura covalent bonds; structure of ethane, ethene etana, etena in etina; polarnost vezi in and ethyne; bond polarity and elektronegativnost; toksičnost kemikalij in varno electronegativity; toxicity of chemicals and delo z njimi. risks. The nature of organic compounds. Narava organskih spojin. Alkanes and cycloalkanes: nomenclature, Alkani in cikloalkani: nomenklatura, izomerija, isomerism, conformations; cis‐trans isomerism konformacije; cis‐trans izomerija pri cikloalkanih, of cycloalkanes, equatorial and axial ekvatorialni in aksialni substituenti pri cikloheksanu; substituents in cyclohexane; physical properties fizikalne lastnosti alkanov, nafta. of alkanes; naphtha. Alkenes and alkynes: Alkeni in alkini: nomenklatura, elektronska nomenclature, electronic structure, cis‐trans struktura, cis‐trans izomerija, pravila sekvence in isomerism, sequence rules and Z,E‐
Z,E‐konfiguracija; tipi organskih reakcij, mehanizmi configuration; kinds of organic reactions; mechanisms, reaction intermediates and in reakcijski intermediati ter prehodna stanja; 1 od 4 transition states; rate of the reaction, kineticsand thermodynamics; synthesis and transformations of alkenes and alkynes; addition reactions, mechanisms, polymerization; natural rubber. Stereochemistry: tetrahedral carbon atom; chirality, optical activity, absolute configuration; enantiomers, diastereo(iso)mers, meso compounds; presentation of the structure, stereochemistry of reactions; chirality in Nature, chiral drugs. Alkyl halides:nomenclature, synthesis and transformations; SN1 and SN2 reactions, E1 and E2 reactions, E1cb; PCB and other pollutants in Nature. Alcohols, ethers andphenols:nomenclature, properties, synthesisand transformations; hydrogen bonding, acidity; cyclic ethers (epoxides); ethanol as chemical, drug and poison. KT
reakcijska hitrost, kinetika in termodinamika; sinteza alkenov in alkinov ter njihove pretvorbe; adicijske reakcije, mehanizmi, polimerizacija, naravni kavčuk. Osnove stereokemije: tetraedrski ogljikov atom in stereokemija; kiralnost, optična aktivnost, absolutna konfiguracija; enantiomeri, diastereoizomeri, mezo spojine; projekcijske formule, stereokemija reakcij; kiralnost v naravi, kiralna zdravila. Alkil halogenidi: nomenklatura, sinteza in pretvorbe alkil halogenidov; SN1 in SN2 reakciji, E1 in E2 reakciji, E1cb; PCB in drugi naravni polutanti. Alkoholi, etri in fenoli: nomenklatura, lastnosti, sinteza in pretvorbe; vodikova vez, kislost alkoholov in fenolov, ciklični etri (epoksidi); etanol kot kemikalija, zdravilo in strup. UL
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Temeljna literatura in viri / Readings: ‐ J. McMurry: Fundamentals of Organic Chemistry, Brooks/Cole Publishing Company, 4th Edition, Pacific Grove 1998, 566 pages (50%). Supplementary reading: (a) P. W. Atkins, M. J. Frazer, M. J. Clugston, R. A. Y. Jones: Kemija, zakonitosti in uporaba (translated by A. Kornhauser, S. A. Glažar), Tehniška založba Slovenije d. d., Ljubljana, 1997. (b) M. Tišler: Organska kemija, 3. popravljena in dopolnjena izdaja, Državna založba Slovenije, Ljubljana, 2005. Cilji in kompetence: Objectives and Competences: Cilj predmeta je, da študent pridobi: Objectives of the course are mastering basic temeljno znanje iz organske kemije tj. poznavanje knowledge of organic chemistry: nomenclature, nomenklature organskih spojin, poznavanje structural features, functional groups, posameznih vrst organskih spojin (po funkcionalnih reactivity, and typical transformations of skupinah) in njihovih strukturnih značilnosti ter organic compounds. Basic knowledge of organic reaktivnosti, poznavanje osnov organske stereochemistry, reaction mechanisms and stereokemije, reakcijskih mehanizmov in intermediates. Knowledge of the basic intermediatov, poznavanje osnovnih principov principles of organic chemistry and accessing organske sinteze. literature sources. Competences: Basic knowledge of organic chemistry: nomenclature, structure, reactivity, toxicity of fundamental organic compounds and basic transformations of organic compounds. Ability to understand structure‐reactivity relationship, i.e. to predict chemical properties of a given 2 od 4 UL
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organic compound from its structure and vice versa. Predvideni študijski rezultati: Intended Learning Outcomes: Znanje in razumevanje Knowledge and Comprehension Študent se nauči osnov organske kemije: Student understands and is familiar with: poimenovanja organskih spojin, posameznih vrst – Structure of organic compounds and organskih spojin (po funkcionalnih skupinah) in functional groups njihovih strukturnih značilnosti ter reaktivnosti, – Isomerisation and nomenclature of organic osnov organske stereokemije, reakcijskih compounds mehanizmov in intermediatov ter osnovnih – Basic transformations of organic compounds principov organske sinteze. – Typical reagents used for performing basic organic reactions Uporaba Application Študent pridobi temeljno znanje, ki je osnova za Mastered knowledge of organic chemistry is nadaljnji študij kemije in se navezuje na večino basic knowledge needed for studding chemical ostalih predmetov študija kemije. To znanje je engineering. The knowledge is interconnected nujno potrebno pri kasnejšem delu v praksi. with majority of other subjects concerning the program. Course is also fundamental for understanding biochemistry subjects and curses concerning organic materials and ecology. Refleksija Analysis Zavedanje, da je za popolno razjasnitev kemijske Student is capable of recognising different basic reakcije potreben natančen študij vsake reakcijske types of organic compounds, predict there stopnje. physical properties, toxicity, reactivity, etc. Skill‐transference Ability Prenosljive spretnosti Pri predmetu se študenti z reševanjem različnih The student acquires skills that are required for problemov izurijo v uporabi znanja in analitičnega a basic synthetic laboratory work and for razmišljanja. handling with chemicals. The knowledge on organic chemistry enables better understanding of the basic principles of other subjects and courses within the study. Metode poučevanja in učenja: Learning and Teaching Methods: Predavanja; seminarji Lectures, seminar work, training by analytical solving of the theoretical problems. Delež (v %) / Načini ocenjevanja: Weight (in %) Assessment: Pisni izpit (nadomestita ga lahko dva Written exam. Written exam can be pozitivno ocenjena kolokvija). passed by two positive partial exams. Reference nosilca / Lecturer's references: ‐ ŠTEFANE, Bogdan. Selective addition of organolithium reagents to BF[sub]2‐chelates of [beta]‐
ketoesters. Organic letters, ISSN 1523‐7060, 2010, vol. 12, no. 13, str. 2900‐2903, doi: 10.1021/ol100620j. [COBISS.SI‐ID 34162181] ‐ WANG, Jingxin, ŠTEFANE, Bogdan, JABER, Deana, SMITH, Jacqueline A. I., VICKERY, Christopher, DIOP, 3 od 4 UL
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Mouhamed, SINTIM, Herman O. Remote C‐H functionalization : using the N‐O moiety as a atom‐
economical tether to obtain 1,5‐ and the rare 1,7‐C‐H insertions. Angewandte Chemie, ISSN 1433‐7851. [Print ed.], 2010, vol. 49, no. 23, str. 3964‐3968, doi: 10.1002/anie.201000160. [COBISS.SI‐ID 34061573] ‐ NAKAYAMA, Shizuka, KELSEY, Ilana, WANG, Jingxin, ROELOFS, Kevin, ŠTEFANE, Bogdan, LUO, Yiling, LEE, Vincent T., SINTIM, Herman O. Thiazole orange‐induced c‐di‐GMP quadruplex formation facilitates a simple fluorescent detection of this ubiquitous biofilm regulating molecule. Journal of the American Chemical Society, ISSN 0002‐7863, 2011, vol. 133, no. 13, str. 4856‐4864, doi: 10.1021/ja1091062. [COBISS.SI‐ID 34845957] 4 od 4