Faculty of Medicine, Masaryk University, Brno Syllabus of the subject-matter required for the Admission Examination CHEMISTRY ____________________________________________________________________ Atoms and molecules. Subatomic particles, atomic and mass numbers. Relative atomic mass of an element, molecular mass of a compound. Amount of a substance, the mole of an element or a compound, Avogadro´s constant. Diatomic elements. The molar mass of a compound, the molar volume of gases at standard temperature and pressure. Names and formulas of common inorganic ions and compounds (translation of a name to a formula, naming of a compound given the formula). Stoichiometric calculations from chemical formulas. Chemical equations, balancing equations, mass relations in chemical reactions. Calculations of reacting masses, amounts of substances (and volumes of gases) from chemical equations. Atomic structure, the electron configuration of elements, the successive filling of the energy sublevels and orbitals by electrons. Valence electrons, s, p, and d elements. The Periodic Table of elements, established names of some groups of elements. The periodicity of the properties of the elements. The positions of the representative (s and p) elements in the table. Transition (d and f) elements, the locations of the metals, and nonmetals. Chemical bonds. The octet rule. Single and multiple covalent bonds, coordinate covalent bond. The typical numbers of covalent bonds for nonmetals. Spatial orientation of covalent bonds, hybridization of atomic orbitals, shapes of simple molecules. Polar covalent bond, electronegativity, polar and nonpolar molecules. The ionic bond and ionic compounds. Weak intermolecular bonding (the hydrogen bond). Solutions - expressing the composition of solutions: mass fraction (percentage by mass), amount-of-substance concentration (molarity), and mass concentration, calculations. Equivalent amounts of acids and bases required for neutralization (titration of an acid with a base). Solutions of nonelectrolytes and electrolytes, dissociation and ionization of electrolytes, strong and weak electrolytes. Concentrations of ions in solutions of strong electrolytes. Types of chemical reactions. Protolytic reactions: Definition of acids and bases (Brønsted), conjugate pairs. Amphoteric compounds and ions. Strong acids and bases. Weak acids and bases, ionization constants. Ionization of water, the ionic product of water. Concentration of hydrogen ions, the pH value. Solutions of strong acids and bases - calculations (for a given concentration or pH value). Hydrolysis of ions (classification of aqueous solutions of the salts as acidic, alkaline, or essentially neutral). Oxidation-reduction reactions, oxidizing agents and reducing agents. Balancing redox equations. Half equations in redox reactions and the numbers of electrons lost or gained. Heats of reaction and other enthalpy changes. Hess´s law. Reaction rate, factors that influence reaction rates. Chemical equilibrium, equilibrium constants, and the general relationship for the equilibrium concentrations of reactants and products. Factors that influence equilibria (changes in temperature, concentration, and pressure). Hydrogen and oxygen, properties, ionic and covalent hydrides and oxides; acid-forming, basic, and amphoteric oxides. Water. Characterictics of some of the elements (chlorine, sulphur, nitrogen, phosphorus, carbon, silicon, alkali metals and alkaline earth metals, iron, copper, aluminium and zinc) and of their important compounds (oxides, hydroxides, covalent hydrides, oxyacids, and salts). Bonds in organic compounds, typical properties of organic compounds. Types of reactions in organic chemistry (reactions by addition, elimination, dehydration, condensation, hydrolysis, oxidation, reduction, etc.). Notation of structural and abbreviated (rational) formulas. Isomerism – various types of structural isomerism and stereoisomerism. Nomenclature of organic compounds: Systematic IUPAC names – general principles in systematic nomenclature: functional names of hydrocarbons and of some groups of compounds, substitutive names for the most organic compounds. Application of these principles in the nomenclature of hydrocarbons and some important groups of organic compounds. The trivial (or semisystematic) names for the most common compounds. Hydrocarbons, names for the groups derived from hydrocarbons. Saturated and unsaturated hydrocarbons, arenes – chemical formulas, typical reactions. Organic halides, nitrocompounds, amines – various types and important structures, basicity of amines, formation of amides. Alcohols and phenols – classification, typical reactions (esterification, ethers, oxidation of alcohols, quinones). Aldehydes and ketones - oxidation and reduction, formation of acetals. Carboxylic acids – reactivity of the carboxyl group. Survey of the common names and structures of the most important carboxylic acids (monocarboxylic and dicarboxylic, saturated and unsaturated, hydroxyacids, ketoacids), names for acyls. Acid halides, anhydrides, esters, amides, nitriles. Urea. Heterocyclic compounds – names and structures of the various common types. The purine and pyrimidine bases of nucleic acids. Uric acid. Saccharides - classification, biological importance, structure of monosaccharides (acyclic oxo-forms, hemiacetal cyclic forms, anomers), formation of glycosides. Reducing and nonreducing disaccharides, polysaccharides. Lipids - fatty acids bound in lipids, acylglycerols, hydrolysis of fats and oils, saponification, soap. Main constituents of phospholipids. Steroids – the structure of the steroid ring system, biological roles of some sorts of steroid compounds. Structures, common and systematic names of the twenty standard (proteinogenous) amino acids, polarity of the side chains. Peptide bond. Proteins – the primary structure, general features of secondary, tertiary, and quaternary structure. Disulfide cross-links, hydrogen bonds and other noncovalent interactions stabilizing the secondary and tertiary structure of proteins, denaturation of proteins. Two main classes of proteins. The general structure of nucleic acids: components of nucleosides and nucleotides, the types of bonds connecting the components, phosphodiester bonds in polynucleotides. The double helix of DNA. The function of DNA and of three major types of RNA in transcription of the genetic code and protein biosynthesis. Six main classes of enzymes. Important hydrolases of the digestive tract. Common chemical names of vitamins. The anabolic and catabolic character of metabolic pathways, importance of biological oxidations in catabolism of nutrients, high-energy (macroergic) compounds and the energetic yield of metabolism. The role of the citric acid cycle and the mitochondrial electron-transport chain. The end products of anaerobic and aerobic glucose degradation, ßoxidation of fatty acids, the nitrogenous end-products of amino acid and purine catabolism. Examples of admission test questions In each question, only one answer is correct at the most (i.e., one or none): - What would be the volume of 12 g of gaseous oxygen at standard temperature and pressure? (The answer should be rounded off to three significant digits.) (A) 8.40 L (B) 192 L (C) 16.8 L (D) 22.4 L - Calculate the pH of a 0.05 mol L-1 solution of potassium hydroxide: (A) 6.50 (B) 12.5 (C) 13.0 (D) 12.7 - Which of the following is the acid-forming oxide? (A) Ag2O (B) CO (C) Mn2O7 (D) N2O - Give the common name of the compound whose condensed formula is HOOC-CH2-CH(OH)-COOH: (A) Lactic acid (B) oxaloacetic acid (C) acetoacetic acid (D) tartaric acid - Which of the following heterocycles is a part of the haemoglobin molecule? (A) Purine (B) porphin (C) pyridine (D) indole Recommended literature: An Overview of Chemistry, Táborská E., Dostál J., Masaryk University Brno, 2010