Topics of the Medical Chemistry exam (2006/2007)
General Chemistry
1/ Basic structure of atoms. Atomic number, mass number. Elements, compounds. Isotopes.
Radioactivity. Avogadro’s number. Definition of mole. Electronic structure of atoms. Building
up principle. Quantum numbers. Atomic orbitals. Pauli exclusion principle. Hund’s rule.
2/ The periodic table. Explanation of periodic properties: relationship to electron configuration.
Periodic classification of the elements. Atomic and ionic radius.
3/ Molecular substances: chemical bonding. Describing ionic, covalent and metallic bonding.
Ionic bonds, ionization energy and electron affinity. Formation of a crystalline solid.
Monatomic and polyatomic ions, naming of these ions and their salts. Metallic bonding.
4/ Describing covalent bonds. Molecular orbital theory. Single and multiple bonds. Bonding
energies. Resonance description, delocalized bonding.
5/ Polar covalent bond. Electronegativity. Dipole moment. Geometrical arrangement of
molecules.
6/ Intermolecular forces: van der Waals forces, London forces, dipole-dipole forces. Hydrogen
bonding. Criteria of H-bond formation. Hydrogen bonding in organic compounds.
7/ States of matter. The gaseous state. State functions. Kinetic theory of gases. Maxwell’s
distribution of molecular speed. Gas laws. The ideal gas law. Real gases.
8/ Liquid state. Changes of state, phase changes related to pressure and temperature. Phase
diagrams. Intermolecular forces. Association of molecules. Solid state. Types of solids;
crystalline solids. The crystalline lattice and crystal systems. Sublimation and lyophilization.
9/ Homogenous and heterogeneous systems. Homogenous systems: mixtures of gases, solutions
and alloys. Microheterogeneous systems: colloidal state. Colloidal size. Properties of colloids.
Types of colloids. Mayor classes: hydrophobic and hydrophilic, dispersed and associated
colloids. (Micelles). Macromolecular colloids.
10/ Types of solutions. The solution process. Factors determining solubility. Saturated solutions.
Solubility and the molecular structure. Concentration of solutions, ways of expressing
concentration. Solubility constant. Solubility of gases. The effect of temperature and pressure
on solubility. Partition coefficient. Osmosis and its biological importance. Osmotic pressure.
11/ Colligative properties of solutions. Vapor-pressure of solutions. Boiling-point elevation and
freezing-point depression. Possibilities of the determination of molecular weights. Baseline of
chromatography.
12/ Chemical equilibrium, law of mass action, equilibrium constant. Le Chatelier’s principle.
Changing the reaction conditions (pressure, temperature and concentration). Application of Le
Chatelier’s principle.
13/ Electrolytes, electrolytic dissociation, degree of dissociation. Strong and weak electrolytes.
Conductivity of electrolytes. Arrhenius concept of acids and bases.
14/ Bronsted-Lowry concept of acids and bases. Conjugate acid-base pairs. Amphoteric
compounds (ampholytes). Molecular structure and acid strength. Lewis concept of acids and
bases.
15/ Equilibrium in electrolytes. Self-ionization of water. Ion product of water. pH and pOH. Acid
and base ionization equilibrium, dissociation constants (Ka and Kb). Solubility of electrolytes,
solubility product constant (Ksp). Reaction of ions with water: hydration, solvation, hydrolysis.
16/ Acidity and basicity of aqueous solutions. Acid anhydrides and base anhydrides. Metathesis
reactions: precipitation reaction, gas formation reaction. Acid-base titration; indicators.
17/ Common-ion effect. Buffers. Application of buffers. Henderson-Hasselbalch equation. Buffer
capacity.
18/ Thermodynamics. State functions (state properties) in thermodynamics. Exothermic and
endothermic reactions. Internal energy. First law of thermodynamics. Heat of reaction and
enthalpy. Hess’s law.
19/ Entropy and disorder. Second and third laws of thermodynamics. Entropy change for a
reaction. Spontaneous reactions. Free energy. Free energy and equilibrium.
20/ Oxidation and reduction. Electrodes and voltaic cells. Electromotive force. Types of
electrodes. Electrode potentials. Strength of oxidizing and reducing agents. Electrical work
and free energy change. Nernst equation. Reaction of metals with water. Redox reactions in the
living states.
21/ Reaction kinetics. Molecularity of a reaction. Reaction rate. Rate equation, rate constant.
Reaction order. Activation energy. Activated complex. Types of complex chemical reactions.
Catalysts. Homogenous and heterogeneous catalysis. Enzymes.
Inorganic chemistry
1/
Hydrogen and its compounds: water, hydrogen peroxide, ammonia, hydrogen sulfide,
hydrides. The noble gases. Electronic structure of noble gases.
2/
Halogens: electronic structure and chemical properties. Hydrogen halides and their salts,
halogen oxoacids and their salts.
3/
The elements of the oxygen group: electronic structure and chemical properties. Oxides,
peroxides, and superoxides.
Hydrogen sulfide and other sulfides. Oxides of sulfur. Oxoacids of sulfur and their salts.
4/
The elements of the nitrogen group: electronic structure and chemical properties. Ammonia.
Oxides of nitrogen. Oxoacids of nitrogen and their salts.
5/
Oxides of phosphorus. Oxoacids of phosphorus and their salts. Halogenated compounds of
phosphorus.
6/
The elements of the carbon group: electronic structure and chemical properties. Oxides of
carbon, carbonic acid and its salts. Silicates.
7/
Alkali metals: electronic structure and chemical properties. Oxides, hydroxides. Salts of
alkali metals.
8/
Alkaline earth metals: electronic structure and chemical properties. Oxides, hydroxides. Salts
of alkaline earth metals. The electronic structure and chemical properties of aluminum. The
amphoteric character of aluminum oxide. Aluminum chloride.
9/
The electronic structure and the periodic trends of d-transition elements. Oxidation states of
d-transition metals. Most important representatives: Mn, Fe, Cu, Pt and Zn.
10/ Complex compounds of d-transition metals. Formation and stability of complexes.
Coordination number. Chelate complexes. Biological importance of chelates.
Organic Chemistry
1/ The geometry of carbon-carbon bonds: hybridization of the carbon atom, sp3, sp2 and sp.
Classification of organic compounds. Functional groups of organic compounds.
2/ Structure, nomenclature and structural isomerism of alkanes (paraffins). Conformation,
conformers of ethane and butane. Nomenclature of alkyl groups. Characteristic chemical
reaction: substitution, free radical mechanism.
3/ Types of organic chemical reactions. Substitution, addition and elimination reactions.
Homolytic and heterolytic reactions, ionic and radical mechanism. Nucleophilic and
electrophilic reagents. Examples for electrophilic addition, substitution (AE and SE) and
nucleophilic addition, substitution (AN and SN).
4/ Structure and nomenclature of cycloalkanes (cycloparaffins). The role of the number of carbon
atoms of the ring in the stability. Conformations of cyclohexane: boat and chair conformations.
Axial and equatorial substituents. Isomerism of disubstituted cyclohexanes. Bi- and polycyclic
alkanes. Chemical properties of cycloalkanes.
5/ Structure and nomenclature of alkenes. Constitutional and cis-trans isomerism. Chemical
reactions of carbon-carbon double bonds: electrophilic addition. Markovnikov’s rule.
Polymerization: ionic and radical mechanism. Alkynes, acetylene, reactions of acetylene.
6/ Polarization in organic compounds; polar covalent bond, inductive effect, functional groups
causing inductive effect. Conjugation effect: position of  electron pairs. Butadiene:
delocalization of double bonds; mesomeric structures. Resonance theory. Partial addition
reaction of butadiene with bromine. Groups having conjugated effect.
7/ Structure of isoprene. Mevalonic acid. Polyisoprene, terpenes. Carotinoids. Vitamin A (retinol)
and retinal.
8/ Aromatic compounds. Structure of benzene. Stability of aromatic compounds. Hückel’s rule.
Structure of naphthalene, anthracene and phenanthrene. Derivatives of benzene: toluene,
xylenes, ethylbenzene, vinylbenzene (styrene). Aryl and aralkyl groups. 3,4 benzpyrene and
carcinogens.
9/ Chemical reactions of aromatic compounds. Electrophilic substitutions: halogenation,
sulfonation, nitration, Friedel-Crafts alkylation and acylation. Mechanism of electrophilic
aromatic substitution. Effect of substituents on aromatic substitution.
10/ Classicification and preparation of organic halogen compounds. Nomenclature of
alkylhalogenids. Mechanisms of nucleophilic substitution. Elimination reactions. Aromatic
halogenated compounds and their reactivity.
11/ Hydroxyl group containing organic compounds: enols and phenols. Classification and
nomenclature of alcohols. Chemical properties. Reactions of alcohols. Some important
alcohols.
12/ The acidity of phenols. Influencing effect of substituents on the acidity. Nomenclature of
phenols. Chemical reactions. Derivatives of phenols. Oxidation of phenols. Some important
phenols and phenol-derivatives. Esters formed from alcohols and inorganic acids: nitrites,
nitrates, sulfates and phosphates.
13/ Nomenclature and preparation of ethers, cyclic ethers and phenolethers. Chemical properties.
Chemical properties of thiols (mercaptans). Oxidation reactions. Thioethers, sulfoxides,
sulfones, sulfonic acids.
2nd semester
14/ Three-dimensional structure of molecules: constitution, conformation and configuration.
Symmetry of the molecules: chiral and achiral molecules. Optical activity. Enantiomers,
racemates. Projection formulas: Fischer projection, D and L system: relative configuration of
glyceraldehyde. R-S system of absolute configuration (Cahn, Ingold and Prelog). Priority
ranking of substituents.
15/ Molecules with more than one chiral centers. Isomers of erythrose and threose. Erithro- and
threo-stereomers in organic compounds. Diastereomers. Isomers of tartaric acid: L-, D- and
meso-isomer. Monosaccharides as compounds containing many chiral centers. Molecular
dissymmetry, allene-isomerism. Resolution: separation of racemates.
16/ Classification and nomenclature of amines. Preparation and steric structure of amines.
Chemical properties of amines. Basicity of amines in aqueous solution and in nonpolar
solvents. Salt formation. Chemical reactions of amines. Biologically important amines and
aminoalcohols. Amines as neurotransmitters. Reactions of amines with nitrous acid, formation
and reaction of diazonium salts. Sulfonamides.
17/ Classification, nomenclature of heterocyclic compounds. Three- and four-membered
heterocycles. Five-membered heterocycles with one heteroatom: furane, thiophene, pyrrole,
aromaticity, structure. Reactions. Five-membered heterocycles with two heteroatoms: oxazole,
imidazole, pyrazole, thiazole.
18/ Six-membered heterocycles with one heteroatom. Pyranes and derivatives: chromane and
flavonoids. Structure, basic character, reactions of pyridine. Derivatives: nicotinic acid and
nicotinamide. Fused rings with benzene: quinoline, isoquinoline.
19/ Six-membered heterocyclic compunds with two heteroatoms. Pyridazine, pyrazine,
piperazine. Pyrimidine and chemical properties of pyrimidine. Derivatives of pyrimidine:
uracil, thymine, cytosine, lactim-lactam tautomerism. Barbituric acid and barbiturates. Purine
and derivatives: adenine and guanine. Uric acid. pteridine and derivatives; folic acid,
riboflavine.
20/ Oxo compounds. The carbonyl group. Nomenclature, chemical properties. Preparation of
aldehydes and ketones. Chemical reactions: nucleophilic addition and condensation reactions.
21/ Reactions of the -carbon in oxo compounds: enol-oxo tautomerism, aldol addition (aldol
dimerization), role in the biological processes. Oxidation and reduction reactions.
Polymerization reactions. Important aldehydes and ketones. Quinones, redox reactions;
ubiquinone (coenzyme Q) and vitamin K.
22/ Classification and nomenclature of carboxylic acids. Preparation of carboxylic acids. Acidity,
dissociation of carboxylic acids, effect of substituents on acidity. Salts, decarboxylation,
esterification.
23/ Homologous series of saturated fatty acids. Importance, representatives. Unsaturated,
polyunsaturated fatty acids: oleic, linoleic, linolenic, arachidonic acids and omega-3unsaturated fatty acids and their role in the biological membranes.
24/ Saturated dicarboxylic acids, important representatives. Chemical properties. Unsaturated
dicarboxylic acids: maleic and fumaric acids. Aromatic mono- and dicarboxylic acids.
Hydroxy carboxylic acids, chemical properties. Lactone formation. Important representatives.
25/ Halogenated carboxylic acids. Oxo acids. Important representatives. Chemical properties.
“Ketone bodies”. Organic derivatives of carbonic acid and their importance.
26/ Carboxylic acid derivatives: esters, thioesters, acyl halides, carboxylic acid anhydrides,
nitriles and amides. Acylation reactions, acylating agents. Acetyl-coenzyme-A.
27/ Mechanism of esterification. Hydrolysis of esters: saponification. Important esters: esters in
fruits, waxes, triglycerids. Soaps, detergents.
28/ Classification of lipids. Phosphatidic acid and its derivatives. Sphingomyelin. Neutral lipids.
Biological membranes.
29/ Classification, structure and nomenclature of amino acids. Proteinogenic amino acids, oneand three-letter abbreviations. Optical activity (stereochemistry) of amino acids. Amphoteric
character: dipolar ions, isoelectric points. Essential amino acids, biological importance of
amino acids. Qualitative tests for amino acids. Preparation of amino acids, resolvatation.
Chemical reactions of the amino and carboxyl groups and the side chains.
30/ Structure and nomenclature of peptides. Stereochemistry of the peptide bond. Conformational
studies on peptides. Chemical synthesis of peptides.
31/ Biological importance of peptides. Naturally occurring peptides. Some important peptide
hormones, peptide analogs. Peptide antibiotics.
32/ Structure and functions of proteins. Physical and chemical properties of proteins: solubility,
amphoteric character. Qualitative tests. Purification of proteins. Proteins and proteids. Threedimensional structure of proteins: primary, secondary, tertiary structures. Denaturation of
proteins.
33/ Biological importance of proteins: transport proteins, contractile proteins, and structural,
nutrient and storage, defense and regulation proteins. Types of enzyme reactions.
34/ Classification of carbohydrates. Configuration of monosaccharides. Structure of D-glucose,
mutarotation of D-glucose, anomers. Cyclic structures: furanose; hemiacetal formation.
Haworth formulas. Conformation of D-glucose.
35/ Chemical properties of monosaccharides: oxidation and reduction reactions: aldonic, aldaric,
and uronic acids, polyalcohols. Identification of monosaccharides. Reactions of the hydroxyl
groups: ester and ether formation. Phosphate and sulfate esters. O- and N-glycosides.
36/ Important monosaccharides: aldoses and ketoses (trioses, tetroses, pentoses, hexoses) and
derivatives. D-glucosamine, D-galactosamine, N-acetyl-derivatives, sialic acid. L-ascorbic acid
(Vitamin C).
37/ Structure of disaccharides. Nonreducing disaccharides: sucrose and trehalose. Reducing
disaccharides: maltose, isomaltose, lactose, cellobiose.
38/ Oligosaccharides. Cyclodextrines and their importance. Oligosaccharides in glycoproteins.
Complex oligosaccharides, structure of polysaccharides. Energy-storage and structural
polysaccharides.
39/ Steroids. Steroidal ring, the fusion of the rings. Classification of steroids. Structure, physical
and chemical properties of cholesterol, cholesterolesters. Ergosterol. Vitamin D2 and D3;
1, 25-dihydroxycholecalciferol.
40/ Bile acids. Conformation of bile acids. Detergent effect. Steroid hormones. Corticosteroids:
mineralo- and glucocorticoids. Sex hormones: androgens, estrogens and progestogens. Steroid
glycosides.
41/ Structure, nomenclature and properties of nucleosides. Structure, nomenclature, chemical and
biological properties of nucleotides. Nucleotide coenzymes.
42/ Nucleic acids, RNA and DNA. Acidic, basic and enzymatic hydrolysis of nucleic acids,
products of the hydrolysis. Primary structure of nucleic acids: 3’,5’-phosphodiester linkage.
Chemical properties of nucleic acids.
43/ Sequence-analysis of nucleic acids, the possibilities of the chemical synthesis of nucleic acids.
The structure of DNA. Biological importance of nucleic acids. Classification of different types
of RNA.
44/ Water-soluble vitamins and their coenzymes.
45/ Biological importance of fat-soluble vitamins. Hypo- and hypervitaminosis.
46/ Appearance, importance, extraction of alkaloids. Classification of alkaloids. Most important
alkaloids (morphine, codeine, papaverine, cocaine, LSD, quinine and ephedrine).
47/ Antibiosis. Classification of antibiotics. Most important antibiotics.
48/ Porphin-ring containing compounds: protoporphyrin-IX and heme. Role of heme in
hemoglobin and myoglobin. Carrying of oxygen and carbondioxide. Chlorophyll.