COURSE OBJECTIVE:
The primary objective of the course is to introduce students to the fundamental principles of modern organic chemistry, understanding the relationship between structure and reactivity of organic compounds, and the application of organic synthesis methods in the biosciences and industry.
COURSE Isyllabus:
1. CARBON COMPOUNDS AND INTRODUCTION TO THE STRUCTURAL THEORY OF ORGANIC CHEMISTRY: introduction to structural theory: empirical and structural molecular formulas, isomers, the tetrahedral structure of methane; chemical bonds ? the octet rule, ionic and covalent compounds, Lewis structures, resonance; quantum mechanics (the Schrödinger wave equation), atomic and molecular orbitals; structure of methane and ethane: sp3 hybridization; structure of ethene: sp2 hybridization, cis-trans isomerism; structure of ethyne: sp hybridization.
2. INTRODUCTION TO ORGANIC REACTIONS: ACIDS AND BASES: Types of chemical reactions and their mechanisms; acid-base reactions, the Br?nsted, Lowry, and Lewis definitions of acids and bases; heterolysis of carbon bonds (carbocations and carbanions), strength of acids and bases, relationship between structure and reactivity of acids, acidity of carboxylic acids, organic compounds as bases; introduction to the mechanisms of organic reactions.
3. CLASSES OF CARBON COMPOUNDS, FUNCTIONAL GROUPS: Hydrocarbons: alkanes, alkenes, alkynes, and aromatic compounds; polar covalent bonds, polar and nonpolar molecules, functional groups in organic molecules, alkyl halides, alcohols, ethers, amines, aldehydes and ketones, carboxylic acids, esters and amides, nitriles. Relationship between the structure and physical properties of molecules (hydrogen bonds, van der Waals forces).
4. ALKANES ? CONFORMATIONAL ANALYSIS AND INTRODUCTION TO SYNTHESIS: Conformational analysis of alkanes, relative stability of cycloalkanes ? ring strain, cis- and trans-isomerism of cycloalkanes, synthesis of alkanes and cycloalkanes, planning organic synthesis ? retrosynthetic analysis (synthons, strategies for functional group interconversion, stereochemical and topological strategies), examples of syntheses of biologically and pharmacologically important molecules based on retrosynthetic analysis.
5. STEREOCHEMISTRY AND CHIRALITY I: biological significance of chirality; isomerism: constitutional isomers and stereoisomers; chiral molecules and enantiomers, nomenclature of enantiomers (Cahn-Ingold-Prelog R, S rules), relative and absolute configuration, optical activity of enantiomers, molecules with multiple stereocenters, meso compounds, Fischer projection formulas, stereoisomerism of cyclic compounds.
6. STEREOCHEMISTRY AND CHIRALITY II: Heteroatoms as stereocenters, axial chirality (atropisomerism), helicity, homochirality in nature, pseudoasymmetry, prochirality, diastereoisomerism, preparation of enantiomerically pure compounds (fractional crystallization of racemates, chromatographic separation of enantiomers on chiral stationary phases), chiral drugs ? interaction of drug enantiomers with receptors.
7. IONIC REACTIONS ? NUCLEOPHILIC SUBSTITUTION REACTIONS OF ALKYL HALIDES: Nucleophilic substitution reactions: nucleophiles, leaving groups; kinetics, mechanism, and stereochemistry of SN2 and SN1 reactions (carbocations); examples of organic syntheses through functional group transformation using SN2 reactions.
8. IONIC REACTIONS ? ELIMINATION REACTIONS OF ALKYL HALIDES: influence of the nucleophile on competing elimination and substitution reactions; mechanism of E1 and E2 reactions, stereoselectivity and regioselectivity of E1 reactions, stereospecificity of E2 reactions of substituted cyclohexanes, regioselectivity in elimination reactions (Hofmann's and Zaitsev's rules), carbanion mechanism of elimination reactions (E1cB).
9. ALKENES AND ALKYNES I: PROPERTIES AND SYNTHESIS: determining the configuration of E- and Z-diastereomers, relative stability of alkenes, cycloalkenes, synthesis of alkenes by dehydrohalogenation of alkyl halides and dehydration of alcohols, carbocation stability and molecular rearrangements, synthesis of alkynes by elimination reactions, acidity of terminal alkynes and substitution of acidic hydrogen atoms of terminal alkynes.
10. ALKENES AND ALKYNES II: ADDITION REACTIONS: addition of hydrogen halides to alkenes (Markovnikov's rule), stereochemistry of ionic addition reactions to alkenes, oxymercuration and demercuration of alkenes (Markovnikov addition), synthesis of alcohols by hydroboration and oxidation of alkenes (syn-hydration, anti-Markovnikov rule), hydroboration of alkenes and synthesis of alkylboranes, addition of halogens to alkenes, stereochemistry of halogen addition reactions to alkenes.
11. DETERMINATION OF THE STRUCTURE OF ORGANIC COMPOUNDS BY NUCLEAR MAGNETIC RESONANCE AND MASS SPECTROMETRY: introduction to nuclear magnetic resonance (NMR) spectroscopy, nuclear spin, shielding and deshielding of protons, chemical shift, chemically equivalent and nonequivalent protons, signal splitting: spin-spin coupling, 1H and 13C one- and two-dimensional nuclear magnetic resonance spectroscopy (1D and 2D NMR), application of nuclear magnetic resonance in medicine; introduction to mass spectrometry, ionization and fragmentation of the molecular ion, determination of molecular formula and mass, application of mass spectrometry in biomedicine.
12. RADICAL REACTIONS: energies of homolytic bond cleavage and relative stability of radicals, selectivity in radical substitution reactions, chlorination of methane ? activation energy, halogenation of higher alkanes, geometry of alkyl radicals, radical additions to alkenes (anti-Markovnikov addition of hydrogen halides), radical polymerization of alkenes, radicals in biology, medicine, and industry.
13. ALCOHOLS: synthesis of alcohols from alkenes, reactions of alcohols, alcohols as acids, conversion of alcohols into alkyl halides, mechanism of the reaction of alcohols with hydrohalic acids, alcohol derivatives with leaving groups: tosylates, mesylates, and triflates, reactions of alcohols with aldehydes and ketones ? formation of hemiacetals and acetals, silyl ethers ? protecting groups for alcohols, sugar alcohols.
14. ETHERS: synthesis of ethers, silyl protecting groups in ethers, reactions of ethers (cleavage of ethers by strong acids), cyclic ethers (epoxides): synthesis by epoxidation of alkenes, Sharpless asymmetric epoxidation of alkenes; reactions of epoxides (acid-catalyzed ring opening, carcinogenicity of epoxides through biological oxidation), crown ethers: phase-transfer catalysts, antibiotic transport and crown ethers.
Prerequisites for course enrollment:
Passed courses: General Chemistry
Attended courses: Inorganic Chemistry, Chemical Analysis of Materials
Prerequisites for taking the course exam:
Passed courses: General Chemistry, Inorganic Chemistry, Chemical Analysis of Materials
Development of students' general and specific competencies:
The primary educational objective is for students to master the principles of organic chemistry and methods of organic synthesis, and their application in the synthesis of new compounds.
Specific competencies: mastering basic techniques for working in the synthesis of organic compounds and their identification.
Student obligations in teaching and methods of fulfilling them:
Attendance at lectures and exercises is mandatory. Continuous knowledge assessment will be conducted through tests during lectures, the results of which will determine exemption from the written part of the exam.
Method of course delivery:
Lectures (ex cathedra) and exercises
Method of knowledge assessment and examination:
Colloquia during the semester, written and oral exam.
Method of monitoring the quality and success of the course:
Student survey
Course learning outcomes:
Analyze the structure of carbon compounds, define organic compounds and the nature of the chemical bond in organic molecules based on molecular orbital theory and hybrid atomic orbitals
Define the basic types of organic reactions and explain the basic reaction mechanisms while recognizing reactive reaction intermediates
Apply IUPAC rules for naming organic compounds and define classes of compounds
Explain the conformations of alkanes and cycloalkanes, define and name isomers
Define the basic synthesis reactions and reactions involving alkanes, alkenes, alkynes, alcohols, ethers, and explain radical reactions
Program-level learning outcomes to which the course contributes:
Explain the scientific foundations important for chemistry and materials engineering, particularly in the fields of chemistry, physics, mathematics, and chemical engineering
Recognize the fundamental elements of chemistry and materials engineering: structure, properties, production, and use of materials
Gather information from various sources
Define simple problems in the field of chemistry and materials engineering in order to solve them
Analyze materials using chemical and physical techniques as well as laboratory equipment and devices
Theoretically interpret the results of experimental work
Organize effective work in the laboratory, independently or as part of a multidisciplinary team
Use appropriate methods and equipment related to the production, characterization, and use of materials, while ensuring occupational safety
Present the results of their work in written and oral form
Develop work ethics, personal responsibility, and a commitment to continuous improvement
Required literature:
T. W. G. Solomons, C. B. Fryhle, Organic Chemistry, J. Wiley, New York, 2003.
L. G. Wade Jr., Organic Chemistry, Pearson Prentice Hall, London, 2006.
J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, Oxford, 2001.
S. H. Pine, Organic Chemistry (Organska kemija), Školska knjiga, Zagreb, 1994.
V. Rapić, Nomenclature of Organic Compounds (Nomenklatura organskih spojeva), Školska knjiga, 3rd revised and supplemented edition, Zagreb, 2004.
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T. W. G. Solomons, C. B. Fryhle, Organic Chemistry, J. Wiley, New
York, 2003.,
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L. G. Wade Jr., Organic Chemisty, Pearson Prentice Hall, London, 2006.,
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J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry,
Oxford University Press, Oxford, 2001.,
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S. H. Pine, Organska kemija, Školska knjiga, Zagreb, 1994.,
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V. Rapić, Nomenklatura organskih spojeva, Školska knjiga, III izmijenjeno i nadopunjeno izdanje, Zagreb, 2004.,
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