AN OUTLINE OF CHEMISTRY EXAM QUESTIONS

for human medicine

  1. Atomic structure. Basic concepts: atom,atomic nucleus, electron shell. Determination of numbers of protons, neutrons and electrons in atoms and ions with given atomic numbers and mass numbers.Quantum numbers n, l, ml, and atomic orbitals.The shapes of orbitals. Shells, subshells, and orbitals. Electron spin, spin magnetic quantum number ms.Orbital energy levels in multielectron atoms. Electron configurations of multielectron atoms: building-up principle (Madelung’s rule), Pauli exclusion principle, Hund's rule.

2.The Periodic Table.Description of groups and periods in the Periodic Table on the base of similarity in the atomic structure. Relationships between atomic electronic configurations, position of the elements in the Periodic Table and their properties.Trends in the Periodic Table: atomic and ionic size, electronegativity, electron affinity, first ionisation energy, highest oxidation number (for s- and p-block groups, and first to thirdrows of elements.

3.Chemical bonding and structure. Basic concepts:chemical bond, covalent bond, shared pair of electrons (bonding pair), polarand non-polar covalent bonds, single, double and triple bonds, ionic bond, crystal lattice, metallic bond, coordinate covalent bond, intermolecular interactions, hydrogen bond.σ- and π-bond formation by overlapping of atomic orbitals: unhybridized (s-, p-), and hybridized orbitals (sp, sp2, sp3).Explanation of the molecular geometry by using of specific hybridization scheme(sp, sp2, sp3). Prediction of the bonding type on thebasis of the electronegativity of the elements.

  1. Thermochemistry. Basic concepts:enthalpy of reaction, endo- and exothermal reactions, enthalpy of formation,enthalpy of combustion. Thermochemicalequations. Hess's law: application to calculation of reaction enthalpy from enthalpy of formation of reactants.
  2. Chemical kinetics. Basic concepts: rate of reaction, rate equation, rate constant. Catalysts, enzymes. Potential energy diagrams of chemical reactions, activation energy. Factors affecting reaction rate: nature and concentration of reagents, temperature (Arrhenius equation)and catalysts.
  3. Chemical equilibrium. Basic concepts: reversible andirreversiblereactions, chemical equilibrium, mass action law and equilibrium constant (K), its determination and meaning. Dependence of K on temperature. Homogeneous and heterogeneouschemical equilibriums.The response of system at equilibrium to the change in pressure, volume, concentration, and temperature.

7.Solutions. Basic concepts: unsaturated,saturated andsupersaturatedsolutions. Stoichiometry of mixtures: calculation of weight %, mole fraction, molarity. Gas in liquids: Henry’s law. Binary liquid mixtures: Roult’s law. Solids in liquids: lowering of vapour pressure. Colligative properties (cryoscopy: depression of freezing point, ebullioscopy:elevation of boiling point, and osmotic pressure).

  1. Solutions ofelectrolytes. Basic concepts: electrolyte andnon-electrolyte, ionization (electrolyticdissociation),ionization (dissociation) constant and degree of ionization,strong and weakelectrolytes. Acids, bases, and salts: Arrhenius theory of acids and bases,neutralization reactions,hydrolysis of salts, Broensted-Lowry theory, conjugate acids and bases.Dissociation of water,ionic product of water, and definition of pH. Solubility product – definition.Exchangereactions between electrolytes: ionic equations, conditions of practical irreversibility of reactions.
  2. Oxidation and reduction. Basic concepts: reducing agent, oxidizing agent, reduction, oxidation, redox reaction. Determination of oxidation number. Balancing redox reactions: the half-reaction method. The activity series of the elements. Electrolysis and its applications.Chemicalsources ofelectric current-galvaniccells.
  3. Chemistry of elements and their compounds. Classification of the elements as metals, nonmetals, metalloids, or noble gases by their properties.
  4. Metals from the A-groups in the Periodic Table and transition metals (Cu, Ag, Zn, Fe) - general characteristics, physical properties, chemical reactions of metals with oxygen, hydrogen, non-metals, water, acids and salts.
  5. General characteristics of nonmetals (carbon, silicon, nitrogen, phosphorus, oxygen, sulfur, halogens), their oxides and hydrides. Reactionsof nonmetalswith oxygen, hydrogen, other nonmetals and metals.
  6. Chemical properties of the basic and acidic oxides. Chemical properties of the bases and acids. Chemical tests for cations (NH4+, Ca²+, Ba²+, Fe³+, Ag+, Cu²+, Pb²+, Al³+, Zn²+) and anions (Cl‾, I‾, S²‾, SO4²‾, CO3²‾). Expression of genetic transitions between elements and their compounds by balanced chemical equations. Mainapplications, biological importanceandenvironmental impactof chemicalelements and theircompounds.

14.The structural theory of organic compounds. Empirical and molecular formulas. Representation of structural formulas: dash, condensed, bond-line, three-dimentional. Homologous series of organic compounds. Structural (constitutional) isomerism – chain isomerism, positional isomerism, functional group isomerism, geometrical (cis/trans) isomerism.

  1. Valence bond theory. Hybridization of atomic orbitals of carbon atoms (sp3, sp2 and sp). Bond angles, bond lengths, bond strength and shapes of organic molecules.
  2. Alkanes and cycloalkanes. Structure of alkanes – constitucional isomerism. Classification of carbon substitution in alkanes (primary, secondary, tertiary, or quaternary). IUPAC nomenclature. Reactions of alkanes and cycloalkanes – oxidation, radical halogenation. Sources and importance of alkanes.
  3. Alkenes. Structure and IUPAC nomenclature of alkenes. Cis/trans isomerism. Reactions of alkenes – addition of bromine and chlorine, hydrogenation. Addition of hydrogen halides and acid-catalyzed hydration. Markovnikov’s rule. Hydroxylation (reaction with KMnO4). Oxidative cleavage of alkenes. Synthesis of alkenes via dehydrohalogenation of alkyl halides and acid-catalyzed dehydration of alcohols.
  4. Alkynes. Structure of alkynes and IUPAC nomenclature. Reactions of alkynes – addition of bromine, chlorine, hydrogen bromide and hydrogen chloride, mercury(II)-catalyzed hydration. Reduction (hydrogenation) of alkynes to alkenes and alkanes. Alkyne acidity – formation of acetylide anions. Synthesis of alkynes from alkenes, alkylation of anions of terminal alkynes with primary alkyl halides.
  5. Aromatic compounds. Structure of benzene. The concept of aromacity. IUPAC nomenclature of benzene derivatives. Substitution reactions of benzene – chlorination, bromination, nitration, sulfonation, Friedel-Crafts alkylation and acylation. Substitution reactions of monosubstituted benzenes – directing, activating and deactivating effects of substituents. Synthetic applications of substitution reactions at benzene derivatives. Reactions of side chains of alkylbenzenes – halogenation and oxidation. Sources and industrial use of aromatic hydrocarbons.
  6. Alkyl halides (haloalkanes). Classification, structure andIUPAC nomenclature of alkyl halides. Isomerism. Reactions – substitution and elimination. Synthesis – by halogenation of alkanes, addition of hydrogen halides and halogens to alkenes and alkynes.
  7. Alcohols and phenols. Structure andIUPAC nomenclature of alcohols and phenols. Isomerism. Hydrogen bonding in alcohols and phenols. Acidity and basicity of alcohols and phenols. Reactions of alcohols and phenols – with active metals, convertion to ethers (Williamson synthesis), conversion to esters (acylation with acid chlorides and anhydrides). Reactions of alcohols – with hydrogen bromide and hydrogen chloride (conversion into akyl halides), acid-catalyzed dehydration (convertion into ethers and alkenes), carboxylic acids (esterification), oxidation. Multifunctional alcohols – glycols and glycerol.Reactions of benzene ring of phenols – (chlorination and bromination, nitration, sulfonation and Kolbe carboxylation). Practical use of alcohols and phenols.
  8. Carbonyl compounds. Structure andIUPAC nomenclature of aldehydes and ketones. Reactions of carbonyl compounds – addition of carbon nucleophiles (Grignard reagents, hydrogen cyanide). Reduction (hydrogenation) of carbonyl compounds. Oxidation of aldehydes (with Tollens’, Fehling’s reagents). Reaction at an -carbon atom in carbonyl compounds – acid-catalyzed and base-promoted halogenation. Industrial use of carbonyl compounds.
  9. Carboxylic acids.Structure andIUPAC nomenclature of carboxylic acids. Hydrogen bonding in carboxylic acids. Acidity and effect of structure on acidity. Reactions of carboxylic acids – with metals, bases, alcohols (esterification), convertion to acid chlorides, anhydrides and amides. Reaction at an -carbon atom – bromination and chlorination. Synthesis of carboxylic acids via oxidation of alkenes, alkylbenzenes, primary alcohols, aldehydes, hydrolysis of nitriles, carboxylation of Grignard reagents.
  10. Carboxylic acid derivatives. Acid chlorides and acid anhydrides – hydrolysis, reactions with alcohols, phenols, ammonia and amines. Esters – reactions (acid-catalyzed hydrolysis, saponification, reduction to alcohols). Amides – reactions (hydrolysis in aqueous acid and in aqueous alkali hydroxydes). Nitriles – reactions (hydrolysis in aqueous acid and in aqueous alkali hydroxydes, reduction to amines). Practical use of carboxylic acids and their derivatives.
  11. Amines. Classification, structure and IUPAC nomenclature. Basicity. Effect of structure on basicity. Reactions of amines – with acids, alkyl halides, acid chlorides and acid anhydrides. Synthesis of aliphatic and aromatic amines – via alkylation of ammonia with alkyl halides, reduction (hydrogenation) of nitro-compounds and nitriles.
  12. Lipids and detergents. Fats and oils – composition, hydrogenation of vegetable oils, saponification. Fatty acids. Soaps – structure, preparation and properties. Synthetic detergents (sodium alkylbenzenesulfonates and sodium alkyl sulfates).
  13. Carbohydrates. Classification of carbohydrates – monosaccharides, disaccharides, polysaccharides.
  14. Monosacchrides. Structure and nomenclature, Fischer projection formulas, cyclic structure of monosaccharides – Haworth projections. Reactions of monosaccharides – ester formation, oxidation (with Fehling’s or Tollens’ reagents) and reduction (hydrogenation). Polysaccharides. Starch (amylose, amylopectin) and cellulose – structure and properties.
  15. Amino acids, Peptides and Proteins. Structure, IUPAC nomenclature. Protein-derived α-amino acids. Chirality. Acid-base properties of α-amino acids. Isoelectric point. Reactions of α-amino acids (with acids, alkali hydoxydes, alcohols). Peptides – hydrolysis. Proteins – structure.
  16. Synthetic polymers. Classification of polymers. Chain-growth polymers (polyethylene, polypropylene, polystyrene, polyacrylonitrile, polymethylmetacrylate, polyvinyl chloride, polytetrafluoroethylene, diene polymers (natural and synthetic rubber), and step-growth polymers (thermosetting polymer, synthesized from phenol and formaldehyde (bakelite), polyesters, polyamides).