1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
Oral exam, 1st semester
Classification of organic transformations.
Electron configuration of carbon. The sp3 hybridization. Nomenclature of alkanes. Homologous
series of alkanes, physical properties. Synthesis of alkanes.
Conformation of alkanes: ethane, butane.
Conformation of cycloalkanes. Isomerism of cycloalkanes.
Isomerism in organic chemistry: definition, types, classification.
Alkanes and cycloalkanes: chemical properties.
Optical isomerism. Specific rotation, symmetry properties, chirality, types of chirality: central
chirality, molecular asymmetry. Structure, naming and representation of chiral compounds.
Relative and absolute configuration.
Molecules with more than one chiral carbon. Separation of racemic mixtures. Preparation of
optically pure compounds. Stereochemical characteristics of chemical transformations.
Bond polarization: inductive and mesomeric effects, conjugation. Mesomeric structures.
The sp2 hybridization. Nomenclature of alkenes. Isomerism of alkenes. Synthesis of alkenes.
Chemical properties I – hydrogenation, oxidation.
Alkenes: chemical properties II – electrophilic additions. Mechanism of electrophilic additions.
Markovnikov’s rule. Polymerization.
Dienes: types, addition reactions. Polymerization.
The sp hybridization. Structure of the acetylenic bond. Synthesis, chemical properties.
Structure of benzene, aromaticity. Synthesis of aromatic hydrocarbons. Addition and oxidation
reactions of aromatics.
Aromatic hydrocarbons: chemical properties. Aromatic electrophilic substitution.
Substituent effects in aromatic SE reactions: reactivity and orientation.
Polycyclic aromatic compounds.
Organic halides: nomenclature, synthesis.
Organic halides: chemical properties I – nucleophilic substitution. Classification of organic halides
based on their reactivity.
Organic halides: chemical properties II – elimination, reactions with metals.
Hydroxy compounds and thio analogs: classification, nomenclature. Synthesis of compounds
containing OH/SH group. Acidity of alcohols, phenols and their thio analogs. Acidity of sulfonic
acids.
Alcohols, phenols and thio analogs: physical properties (hydrogen bonding) and chemical
properties.
Ethers and sulfides: classification, nomenclature, structure, synthesis. Chemical properties. Cyclic
ethers, crown ethers.
Nitro compounds.
Amines: classification, nomenclature, physical properties (hydrogen bonding), synthesis. Chirality
of amines.
Amines: chemical properties. Basicity of amines.
Diazomethane. Diazonium compounds. Azo compounds.
Carbonyl compounds: classification, nomenclature, structure, synthesis. General reactivity in
nucleophilic additions. Reversibility.
Carbonyl compounds: chemical properties I – nucleophilic additions.
Carbonyl compounds: chemical properties II – enolization, acidity of enols, reactions of the enolate
anion; oxidations and reductions.
Carboxylic acids and derivatives: classification, nomenclature. Structure of the carboxyl group.
Acidity of carboxylic and dicarboxylic acids. Chemical properties: decarboxylation, reduction.
Carboxylic acids and derivatives: physical properties, synthesis. General reactivity of carboxylic
acid derivatives.
Carboxylic acids: chemical properties – nucleophilic acyl substitutions.
Substituted carboxylic acids: dicarboxylic acids, hydroxycarboxylic acids, ketocarboxylic acids.
Carbonic acid derivatives.
Carbocations: types, stability; role in organic transformations.
Exam test, 1st semester
Nomenclature
Draw the structure of the following compounds!
styrene, Z-but-2-ene, allene, isoprene
biphenyl, tropylium ion, ortho/para-xylene, 9,10-dihydroanthracene, cyclopentadienide ion,
phenanthrene, tetralin
methylene chloride, isobutyl chloride, benzyl chloride, sec-butyl chloride, vicinal dihalogen
primary alcohol, allyl alcohol, ethylene oxide, ortho/para-cresol, anisole, tetrahydrofuran, glycerol,
cis/trans-2,3-dimethyloxirane, ethoxy group, ethylene glycol, enol, geminal diol
tosyl group, para-toluenesulfonic acid, dimethyl sulfoxide, diethyl disulfide, sulfanilamide
benzenediazonium chloride, secondary amine, tertiary amine, N,N-dimethylpentanamine, azobenzene,
nitronic acid, imine
acetaldol, benzaldehyd cyanohydrin, acetal
N,N-dimethylformamide, acetanilide, meso-tartaric acid, acetyl chloride, ethyl acetoacetate, aspirin,
acetic anhydride, ketene, acetonitrile, lactol, lactone, lactam, malonic acid, diethyl malonate,
salicylic acid, acetoacetic acid, maleic anhydride, alkyl carbamate/urethane, phosgene, isocyanic
acid, urea, guanidine
Stereochemistry
Determine the absolute configuration
CH2Br
COOH
OH
OH
CH2
CH2
CD2
OH
CH3
CH2
CH2
CH2
Me C NH2 Br C NH2 ClCH2 C H CH3CH2 C CH2SH
CH2
CH2
CDH
CH2
CH2
CH2OH
CH2OH
OH
OCH3
OMe
CH2 CH C CCl3 Me C H
CH2
CH3
Draw the equilibrium chair conformations of cis-1-chloro-2-methylcyclohexane/ trans-1-chloro-2methylcyclohexane, interpret E2 elimination, and the draw the structure of the product(s)!
Draw the energy diagram of SN2/SN1/E2/E1 reactions and insert structure/formula of the corresponding
starting materials/products/intermediates/transition states. Indicate the activation energy of the process
and interpret molecularity.
Draw the energy diagram of the reaction of buta-1,3-diene with HBr. Insert structure/formula of the
corresponding starting material/products/intermediate/transition states.
Draw the structure of the leaving groups formed in the nucleophilic substitution of the following
compounds and the corresponding conjugate acids. Rank the leaving groups according to their leaving
ability.
O
R O H
R O S R'
O
R NH2
R F
+
R N N
R Br
+ H
R O
H
+
R NH3
R Cl
R
I
R S H
Interpret the acidity of alcohols/phenols/enols/carboxylic acids/sulfonic acids on the basis of groundstate polarization and the stability of the corresponding anions (indicate bond polarization and draw
resonance structures)!
Definitions
conformation, conformer, chiral compound, chiral center, prochiral compound, racemic mixture, meso
compound, configuration, retention, inversion, racemization, resolution, enantiomer, asymmetric
synthesis, molecular asymmetry, diastereomerism, nucleophile, electrophile, degree of oxidation,
primary / secondary / tertiary carbon, addition, elimination, substitution, functional group, isomerism,
homologous series, atomic orbital, angular (Baeyer) strain, torsional (Pitzer) strain, tautomerization,
molecularity
Reactions: 1–92
Nomenclature
Name the following compounds/groups! (substitution names, functional group or common names)
COOH
H
C OH
H
C OH
O
CH CH2
Me
COOH
O
O
meso tartaric acid
styrene
9,10-anthraquinone
R
..
cyclopentadienide ion
9,10-dihydro-phenanthrene
tetralin
trans-2,3-dimethyloxirane
N R"(H)
C
R'
:CH2 N
O
tropylium ion
Me
O
ethylene oxide tetrahydrofuran
oxirane
imine
SO2
CH3
NH2
CH3
SO2OH
SO2NH2
Br
diazomethane
Cl
CH2
N
OCH3
CH3 SO2
mesyl group
tosyl group para-toluenesulfonic
acid
CH3
CH2
C
C
O
Me2N CH2CH2CH2CH3
H
CH3
isoprene
bromobenzene benzyl chloride
CH3
H
C CH CH2
sulfanilamide
E-but-2-ene
CH3 C N
NHOCCH3
N N
N N Cl
acetanilide
benzenediazonium
chloride
azobenzene
CH3
Cl
C OH
para-cresol
enol
CH3
resorcinol
benzol-1,3-diol
CH3CHCH3
CH3CHCH2 Cl
CH3CH2CH2CH2
OH
Cl CH3CH2CHCH3
O
O
4-hydroxybutanoic acid
lactone
Ac2O
O
CH3CH2CH2 O
CH3 O
methoxy group propoxy group
CH2 CH Cl
CH3CH2CHCH3
vinyl chloride
C O
H2N
alkyl carbamate
urethane
CH3CCH2CH2
O
CH3CHCH2C
CH3CCH2COOH
H
OH
butan-2-ol
3-hydroxybutanal
sec-butyl alcohol
CH3CCH2COOEt
O
ethyl acetoacetate
O
acetoacetic acid
3-oxobutanoic acid
NH
C
N
H
O
5-amino-pentanoic acid
lactam
O
C
O
maleic anhydride
OH
O
4-hydroxybutan-2-one
O
COOH
malonic
acid
RO
C O
OH
sec-butyl chloride
O
aniline acetic anhydride
ethyl chloroformate
COOH
CH2
CH3C
allyl chloride
Cl
butyl chloride
H
hydroquinone
benzol-1,4-diol
CH2 CH CH2 Cl
Br
isobutyl chloride isopropyl bromide
O
C CN
EtO
OH
R
phosgene
CH3C
benzaldehyde
cyanohydrin
HC
OH
C O
Cl
OH
OH
R'
Cl
H C
NMe2
acetonitrile N,N-dimethylformamide
OH
NH2
N,N-dimethylbutanamine
anisole
H2N
C
NH2
guanidine
Grading
Nomenclature (10 names+5 structures, 15=3 pts, 14=2 pts, 13=1 pts, 12=0.5 p)
Stereochemistry (2 questions)
16 reactions (16 x 1 pt)
2 general questions (energy diagram–2pts, leaving groups–1 pt, acidity–1 pt)
10 definitions (10 correct answers = 3 pt, 9 = 2 pts, 8 = 1 pt)
 3 pts
 2 pts
 16 pts
 3 pts
 3 pt
27 pts
27/26 pts = 5
25 pts = 4,5
24 pts = 4
23 pts = 3,5
22/21 pts = 3
20/19 pts = 2,5
18–16 pts = 2
15.5 pts and less = failed
1. Everybody qualified for exemption from the written test (12 mark points or higher for the 3 tests)
must write a simple test including questions of nomenclature, stereochemistry and definitions (3+2+3
points). Requirement: at least 5 points but with at least 1 point for each type of question.
2. Anybody having a successful written test but with 0 point for nomenclature (less than 11 correct
answers for 15 names/structures) and/or definitions (less than 8 correct answer out of 10) has to write
the nomenclature question and/or definitions to be eligible for oral exam (nomenclature: at least 11
correct answers for 15 names/structures; definitions: at least 8 correct answers out of 10).
3. In the case when a successful written test is followed by a failed exam, the written test remains valid
for all oral exams but it can be retaken once.