Learning outcomes expected at the level of the course (4 to 10 learning outcomes) |
After completing the course, the student will become familiarized with the major concepts of organic chemistry, which includes:
- identifying and naming of organic compounds according to functional groups and compare their physico - chemical properties;
- learn about the organic compounds isomerism, stereochemical designations, features, and separation;
- learn about organic compounds structure determination by spectroscopy (MS, NMR, IR, and UV/Vis);
- analyze the reactivity of organic compounds with respect to their structure and stereochemistry;
- propose appropriate reaction mechanisms of organic molecules that include addition, substitution and elimination;
- identify and interpret division, structure and properties of natural organic compounds ( carbohydrates, nucleic acids and lipids ).
- After performing laboratory practice student will be able to use laboratory techniques (such as extraction, distillation, reflux, chromatography, recrystallization, infrared spectroscopy, etc.), for (i) purification, (ii) isolation, (iii) synthesis, and (iv) identification of the organic compounds. |
Course content broken down in detail by weekly class schedule (syllabus) |
LECTURES AND SEMINARS:
1. Introduction: What is organic chemistry? History of organic chemistry and its modern role. The main concepts of organic chemistry (functional groups, stereochemistry, curly arrows) (2 hours)
2. The nature of chemical bonds: Electronegativity. Bonds polarity, dipol, and formal charge. Lewis structure. Atomic orbitals. Molecular orbitals. Hybridization (sp3, sp2, sp). Length and energy of the bonds. The molecular geometry. The modified hybrid orbitals. VSEPR theory. (4 hours)
3. Physical properties and intermolecular connections: Van der Waals forces. Dipole - dipole. ”Hydrogen bond”. Solubility in solvents. (2+1 hours)
4. Nomenclature and classes of organic compounds. Hydrocarbons (alkanes, cycloalkanes). Functional groups and acronyms. The nomenclature of hydrocarbons (alkenes, alkynes). Nomenclature organohalogenated compounds, alcohols, amines. Nomenclature of aldehydes and ketones, carboxylic acids, acid derivatives. Systematic (IUPAC) nomenclature. Examples. (7+2 hours)
5. Structure of molecules and isomerism. Constitutional isomers. Alkanes. Isomers. Shapes of molecules and IHD. Stereochemistry. Conformations of alkanes (ethane, butane) and rings (C3, C4, C5, cyclohexane). Mono-substituted cycloalkanes. (3+1 hours)
I. PARTIAL EXAM (written, 1hour and 10 min)
6. Configuration of the cis / trans and E / Z; CIP rule. Conformations of disubstituted cycloalkanes. Alkenes. Chirality and the plane of symmetry. Molecules with one stereocenter. Enantiomers and racemic mixtures. The properties of the enantiomers. Optical activity. Polarimeter. Determination of tetrahedral stereogenic center. Fischer projections. Relative configuration. Molecules with two stereocenter. The properties of enantiomers, diastereomers and meso compounds. The separation of the racemate. Chiral molecules without stereocenter. (9+2 hours)
7. Determining organic structures. Introduction. Mass spectrometry (MS). Resolution. Molecular ion. Isotopes. Fragmentation. Examples of mass spectra. Electromagnetic radiation. Ultraviolet and visible spectroscopy (UV/Vis). Infrared spectroscopy (IR). Nuclear magnetic resonance (NMR). 13C NMR. 1H NMR. Chemical shift. Spin-spin coupling. Examples of IR, and NMR spectra. (6+3 hours)
8. Organic reactions. Definitions of basic terms. The division of reactions to the change of structure and to the reaction type. Acidity, basicity, and pKa. Factors that enhance the acidity (the size of atoms, electronegativity, resonance, hybridization, inductive effects, charge, solvation, steric effects). Acid - base reactions. The rules for determining the oxidation state of carbon. Oxidation - reduction reactions. Usage of the curly arrows in the reaction mechanism. Intermediates. Nucleophiles and electrophiles. (4 hours)
II. PARTIAL EXAM (written, 1hour and 10 min)
9. Alkanes and cycloalkanes. Oxidation. Halogenation. Alkyl halides. Nucleophilic substitution at the saturated carbon (SN1 and SN2 mechanism). Elimination reactions (E1, E2 mechanisms). Alkenes and alkynes. Electrophilic additions and free radical, polymerization. Conjugated unsaturated compounds. 1,2 - and 1,4 - addition. Aromatic compounds. Electrophilic and nucleophilic aromatic substitution. Phenols. Alcohols and ethers. Organometallic compounds. Aldehydes and ketones. Nucleophilic addition to the carbonyl group. Carboxylic acids and derivatives. Nucleophilic substitution at the carbonyl group. Amines. Heterocyclic compounds. (18+5 hours)
10. Carbohydrates. Amino acids. Nucleic acid. Lipids. (5+1 hours)
III. PARTIAL EXAM (written, 1hour and 10 min)
IV. PARTIAL EXAM (oral, 30 min)
LABORATORY EXERCISES:
Laboratory safety and rules. Isolation and purification of organic compounds. Crystallization and melting point determination. Distillation. Extraction. Organic compounds synthesis. Diazotation. Carbonyl compounds-nucleophilic addition. Carboxylic acid derivatives-nucleophilic substitution. Electrophilic aromatic substitution. Oxidation-reduction reactions. Chromatography. Thin-layer chromatography. Column chromatography. Organic compounds characterization. Characteristic reactions of functional groups. Methods of spectroscopic analysis. |
