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Module 1. Fundamentals of the structure of organic compounds. Hydrocarbons
(alkanes, cycloalkanes, alkenes, alkadienes, alkynes, arenes) and their functional
derivatives (halogen, nitrogen containing compounds, hydroxyderivatives of
hydrocarbons). Aldehydes and ketones.
What type of chemical reactions is characteristic for alkanes?
elimination (E)
radical substitution (SR)
nucleophylic substitution (SN)
electrophylic substitution (SE)
electrophylic joining (AE)
ANSWER: B
2. Racemic mixture:
A. contains asymmetric molecules of the certain compound
B. contains equal quantities of diastereomers
C. contains chiral molecules of the certain compound
D. contains equal quantities of enantiomers
E. contains achiral molecules of the certain compound
ANSWER: D
3. The different spatial localization of atoms or atom groups in the molecule as a result of its rotation around
σ-bonds is named:
A. optical isomery
B. geometrical isomery
C. structural isomery
D. configuration
E. conformation
ANSWER: E
4. Optical activity is measured using an instrument called:
A. spectrophotometer
B. manometer
C. thermometer
D. polarimeter
E. refractometer
ANSWER: D
5. What carbon atom is chiral?
A. does not have any substituents
B. has 3 types of the substituents
C. has 4 different substituents
D. has 1 type of the substituents
E. has 2 types of the substituents
ANSWER: C
6. Conformation is:
A. the different spatial localization of atoms or atom groups in the molecule as a result of its rotation around
π-bonds;
B. the phenomenon of existence of compounds which are similar by qualitative and quantitive structures but
are different by locations of bonds in molecule.
C. the different sequence of atoms in the molecule of the organic compound;
D. the different locations of identical functional groups and double or triple bonds;
E. the different spatial localization of atoms or atom groups in the molecule as a result of its rotation around
σ-bonds;
ANSWER: E
7. In which sequence the stability of alkyl radicals: methyl, primary, secondary tertiary decreases?
A. primary < CH3< secondary < tertiary
B. primary > CH3> secondary > tertiary
C. tertiary > primary > secondary > CH3
D. CH3> primary > secondary > tertiary
1.
A.
B.
C.
D.
E.
E. tertiary>secondary>primary>CH3
ANSWER: E
8. Free radicals are:
A. charged particles containing not coupled electron
B. not charged particles containing not coupled electron (one-electronic orbital)
C. the particles containing trivalent carbon atom with lone electronic pair
D. intermediate active particles containing negatively charged carbon atom
E. intermediate active particles containing positively charged carbon atom
ANSWER: B
9. Free radicals are formed as a result of:
A. homolytic cleavage of covalent bond in a molecule
B. metallo organic compounds ionization
C. actions of the strong bases on compounds with enough polar C-H bond
D. proton addition or another electrophilic particle to one of the atoms bonded to
each other with double or triple bond
E. direct compound ionization in strongly polar media
ANSWER: A
10. Carbcations - are:
A. charged particles containing not coupled electron
B. not charged particles containing not coupled electron (one-electronic orbital)
C. particles containing trivalent carbon atom with lone electronic pair
D. intermediate active particles containing negatively charged carbon atom
E. intermediate active particles containing positively charged carbon atom
ANSWER: E
11. As a result of homolytic cleavage of the chemical bond are formed?
A. only anions
B. free radicals and ions
C. free radicals
D. only cations
E. cations and anions
ANSWER: C
12. As a result of heterolytic cleavage of chemical bond are formed?
A. free radicals and ions
B. only anions
C. only cations
D. cations and anions
E. free radicals
ANSWER: D
13. In which of the following organic reactions mechanisms as intermediate active particles ions are formed?
A. Heterolytic
B. Homolytic
C. Trimolecular
D. Bimolecular
E. Monomolecular
ANSWER: A
14. Conformers are:
A. Stereoisomers, having a various spatial arrangement of atoms in a molecule and possessing the greatest
stock of energy
B. Compounds, differing by an arrangement of substitutes concerning a plane of double bond
C. Isomers, differing by an arrangement of functional groups
D. Conformations with the least stock of energy
E. The compounds differing from each other by an arrangement of atoms in a molecule in space concerning
multiple bond
ANSWER: D
15. Configurational isomers are:
A. the organic compounds with a various spatial arrangement of atoms in a molecule, caused
by rotation around of p -bond
B. isomers, differing by an arrangement of functional groups
C. isomers, differing by an arrangement of multiple bonds
D. the organic compounds with a various spatial arrangement of atoms in a molecule, caused
by rotation around of s-bond
E. the organic compounds differing from each other by a relative arrangement of atoms in a molecule in
space
ANSWER: E
16. Isomers of carbon chain (carbon skeleton) - compounds which are differ in:
A. arrangement of atoms and atomic groups in space
B. position of multiple bond in a molecule
C. the nature of functional groups
D. various sequence of linkage of the atoms forming a carbon skeleton of a molecule
E. various position of functional groups in a molecule
ANSWER: D
17. Enantiomers - are isomers, which are:
A. represent the racemate
B. have the various order of linkage of carbon atoms in a molecule
C. have an identical configuration at one of asymmetrical carbon atom, but various at other one
D. differ by configuration at one of asymmetrical carbon atoms
E. contain asymmetrical carbon atoms and related to each other as a subject and its mirror image
ANSWER: E
18. Asymmetrical (chiral) carbon atom is?
A. Out from a plane of double bond
B. In sр-hybridization
C. In sр2-hybridization
D. Contacted with four various substituents
E. In sр3-hybridization
ANSWER: D
19. What is the radical name which shown: CH3-CH2-CH2-?
A. Isobutyl
B. Methyl
C. Isopropyl
D. Butyl
E. n-propyl
ANSWER: E
20. To which class of compounds does ethylene glycole (ethandiol-1,2) belong?
A. carboxylic acids
B. alcohols
C. ketones
D. aldehydes
E. phenols
21. What is class of compound: CH3-O-CH3?
A. Ethers
B. Carboxylic acids
C. Ketones
D. Aldehydes
E. Alcohols
ANSWER: A
22. What is the name of the functional group –SH?
A. cyano-group
B. mercapto-group
C. imino-group
D. amino-group
E. sulfuric group
ANSWER: B
23. What class of compound: CH3-CH2-OH?
A. Thiols
Carboxylic acids
Ketones
Aldehydes
Alcohols
ANSWER: E
24. What is the name of the functional group shown below:-NO2?
A. nitrozo-group
B. sulfuric group
C. carboxylic group
D. amino-group
E. nitro-group
ANSWER: E
25. What is the name of the functional group: =NH?
A. nitrozo-group
B. hydroxy-group
C. imino-group
D. amino-group
E. nitro-group
ANSWER: C
26. What is the name of the functiona;l group -NH2?
A. mercapto-group
B. nitro-group
C. imino-group
D. amino-group
E. diazo-group
ANSWER: D
27. In saturated organic compounds the atom of Carbon has:
A. sp5-hybridization
B. sp4-hybridization
C. sp3-hybridization
D. sp2-hybridization
E. sp- and sp2-hybridization
ANSWER: C
28. Alkenes are organic compounds that:
A. contain two double - C - C - bonds
B. contain Carbon cycle
C. contain - C - C – and triple bond (- C ≡ C - )
D. contain only one - C - C – and double bond (- C = C -)
E. contain only - C - C - and - C - H - σ bonds
ANSWER: D
29. What type of chemical reactions is characteristic for alkanes?
A. elimination (E)
B. radical substitution (SR)
C. nucleophilic substitution (SN)
D. electrophilic substitution (SE)
E. electrophilic addition (AE)
ANSWER: B
30. What are the products of the reaction C6H5−ONa + C2H5−Br ↔?
A. C6H5−O−C2H5 + Na + Br2
B. C6H5−O−C2H5 + NaBr
C. C6H5−ONa + C2H5−Br
D. C6H6 + NaBr + C2H6
E. C6H5−OBr + C2H5−Na
ANSWER: B
31. The products of reaction CH3−O−CH3 + HI → are:
A. CH4 +HOH + CH3I
B. CH3−OI + CH4
B.
C.
D.
E.
C. CH3−OH + CH3−OH
D. CH3−OH + CH3I
E. CH2I−O−CH3 + H2
ANSWER: D
32. The general formula of saturated monothio alcohols is:
A. CnH2nSH
B. CnH2n-3SH
C. CnH2n+2SH
D. CnH2n-2SH
E. CnH2n+1SH
ANSWER: E
33. Mercaptane group is:
A. -N=N−
B. -Hg
C. -SN
D. -SCN
E. -CN
ANSWER: C
34. What is the product of reaction of ethanol with acetic acid?
A. ethylacetate
B. acetoasetic ether
C. ethyl formiate
D. diethyl ether
E. acetanhydride
ANSWER: B
35. The general formula of saturated monohydroxy alcohols is:
A. CnH2nOH
B. CnH2n-3OH
C. CnH2n+2OH
D. CnH2n-2OH
E. CnH2n+1OH
ANSWER: E
36. To distinguish glicerol and ethanol it is necessary to use:
A. FeCl3
B. Cu(OH)2
C. HBr
D. KMnO4
E. [Ag(NH3)2]OH
ANSWER: B
37. Choose the right name of the next compound CH3−C≡C−CH2−CH2−OH:
A. pentyne-3-ol-5
B. pentyne-2-ol-5
C. 5-hydroxypentyne-2
D. pentyne-3-ol-1
E. 2-propinylethanol
ANSWER: D
38. Sulphanilic acid has acidic centre:
A. SO2NH3
B. SO2NH2
C. -SO3NH2
D. -SO3H
E. -SO2H
ANSWER: D
39. Aniline C6H5NH2 is:
A. crystal solid. It is formed in the process of rotting of corpses. In the human organism it is used for
synthesis of biologically active polyamines which take part in the biosynthesis of DNA and RNA.
B. gas with the smell of ammonium. Methylamine is used in the production of medicines, dyes, insecticides
and fungicides
C. white crystal solid. It is used as stimulator of CNS
D. liquid. It is formed in the process of rotting of corpses like putrescin
E. colourless liquid with peculiar smell. It is poisonous. It is used in the process of synthesis of dyes,
medicines, plastic materials
ANSWER: E
40. The products of reaction CH3CH2NH2 + CH3I → are:
A. C2H5NO3 + H2
B. C2H5NO3 + H2O
C. C2H5NO2 + H2O+ CH3I
D. C2H5NO2 + HI
E. CH3CH2NHCH3 + HI
ANSWER: E
41. The products of reaction C2H5Cl + H2O ↔ are:
A. C2H5OH + Cl2
B. C2H5OCl + H2
C. CH3Cl + CH3Cl + H2O
D. C2H5OCl + H2O
E. C2H5OH + HCl
ANSWER: E
42. For the aromatic hydrocarbons the most character are reactions of:
A. Nucleophilic substitution
B. Electrophilic accession
C. Electrophilic substitution
D. Elimination
E. Radical substitution
ANSWER: C
43. Reactions of nitration, sulfonation, alkylation, acylation for aromatic hydrocarbons go by the following
mechanism:
A. Free radical substitution
B. Electrophilic substitution
C. Nucleophilic accession
D. Elimination
E. Nucleophilic substitution
ANSWER: B
44. Name the mechanism of the toluene nitration by the benzene ring.
A. SE
B. E1
C. E2
D. SN1
E. SN2
ANSWER: A
45. Name the mechanism of the substitution reaction in benzene molecule.
A. SE
B. SE and SN
C. SR
D. SN
E. SR and SN
ANSWER: A
46. Hydroxyl group in phenol molecule is orients in the following locations:
A. -o
B. –о, -m
C. -m
D. -m, p
E. –о, -p
ANSWER: E
47. Which of the following compounds belongs to carbocyclic?
Furan
Benzene
Tetrahydrofuran
Pyridine
Hexane
ANSWER: B
48. Reaction of the transformation of toluene in benzoic acid takes place in the following conditions:
A. Action of hydrogen peroxide at the room temperature
B. Heating with sulfate acid
C. Boiling with potassium permanganate
D. Action of sodium hydroxide at the room temperature
E. Boiling on the air
ANSWER: C
49. Which of the following substitutes belongs to the meta-orientants?
A. -ОН
B. -C2H5
C. -N(CH3)2
D. -СООH
E. -NH2
ANSWER: D
50. Substituent of the II type (m-orientant) is:
A. Amino-group
B. Hydroxyl group
C. Alkyl group
D. Halogen
E. Carbonyl group
ANSWER: E
51. Which of the following substitutes belongs to the meta-orientants?
A. -SO3H
B. -OH
C. -C2H5
D. -Cl
E. -Br
ANSWER: A
52. Which of the following substitutes belongs to the orto- and para-orientants?
A. Carboxyl group
B. Nitro-group
C. Aminogroup
D. Carbonyl group
E. Sulfo-group
ANSWER: C
53. Which of the following substitutes does not belong to the meta-orientants in the electrophilic substitution
reactions in benzene ring?
A. NO2
B. NH2
C. COH
D. SO3H
E. COOH
ANSWER: B
54. According to the Hukel’s rule number of A-electrons in the aromatic system determine by the formula
(4n + 2). What number of --electrons acridine molecule contains?
A. 6
B. 10
C. 8
D. 14
E. 12
ANSWER: D
A.
B.
C.
D.
E.
55. One of the conditions of formation of aromatic system is Hukel’s rule, according to which the number of
electrons that take part in the conjugation, express by the following formula:
4n
n+2
4n + 2
2n + 2
n + 4, where n = 1,2,3,4
ANSWER: C
56. At the reduction of nitrobenzene in alkali medium it is possible to obtain separate any of the following
compounds. Which of these compounds is the end product of this reaction?
A. nitrobenzene
B. aniline
C. phenylhydroxylamine
D. azobenzene
E. hydrazobenzene
ANSWER: B
57. Which of the following compounds form at the reduction of nitrobenzene by Zinin’s reaction?
A. Nitrobenzol, phenylhydroxylamine, azoxibenzol, azobenzol, hydrazobenzol, aniline
B. nitorbenzol, phenylhydroxylamine, aniline
C. Aniline and nitroaniline
D. Azoxibenzol and benzoldiazonium chloride
E. Nitrobenzol, benzoldiazonium chloride
ANSWER: A
58. What color has methylorange in acidic medium?
A. purple
B. yellow
C. colorless
D. pink
E. red
ANSWER: E
59. What color has methylorange in alkali medium?
A. purple
B. yellow
C. colorless
D. pink
E. red
ANSWER: B
60. What color has methylorange in neutral medium?
A. purple
B. pink
C. colorless
D. orange
E. red
ANSWER: D
61. What compound has the most basic properties?
A. CH3–NH2
B. CH3–OH
C. CH3–SH
D. CH3–O–CH3
E. CH3–S–CH3
ANSWER: A
62. Which reaction can be used to distinguish trimethylamine and n-propylamine?
A. alkylation
B. acylation
C. interaction with HCl
D. isonitrile test
E. interaction with dil. H2SO4
A.
B.
C.
D.
E.
ANSWER: D
63. Definitions “primary”, “secondary”, “tertiary” in amines associated with:
A. Dependence near which carbon atom (primary, secondary or tertiary) is amino-group
B. Number of amino-groups in the molecule
C. Number of hydrocarbons residues near nitrogen atom
D. Nature of hydrocarbon groups near nitrogen atom
E. Number of σ-bounds which nitrogen atom
ANSWER: C
64. For the amines alkylation use:
A. acetic anhydride
B. alkanes
C. halogenalkanes
D. acetic acid
E. halogenanhydrides of the carboxylic acids
ANSWER: C
65. What reagent can be used to distinguish glycerol from ethyleneglycol?
A. NaNО2
B. NaOH
C. Na met.
D. Cu(OH)2
E. KHSO4
ANSWER: E
66. Name the product of interaction of ethyl alcohol and acetic acid:
A. acetanhydride
B. diethyl ether
C. ethylacetate
D. ethylformiate
E. ethylformiate
ANSWER: C
67. Chose the secondary alcohol:
A. СН3- СН(ОН)-СН3
B. СН3 -СН2 -СН2 -ОН
C. НО-СН2 -СН2-ОН
D. (СН3)2-С(ОН)-СН3
E. СН2=СН-СН2-ОН
ANSWER: A
68. Which of the following acids belongs to OH-acids:
A. ethaneamine
B. ethane
C. acetone
D. ethanol
E. benzene
ANSWER: D
69. Choose the reagent, which can be used to obtain propanol-2 from acetone:
A. HCOH
B. CH3OH
C. CH3I
D. HCN
E. Н2
ANSWER: E
70. Which of the following compounds will interact with Сu(OH)2?
A. Pentanol-2
B. Ethanol
C. Propanol-1
D. Isobutyl alcohol
E. Ethanediol-1,2
ANSWER: E
71. What reagent can be used to distinguish glycerol from ethanol?
A. Cu(OH)2
B. HBr
C. FeCl3
D. KMnO4
E. Ag2O
ANSWER: A
72. Choose correct name of glycerol by the international nomenclature:
A. Propanetriol-1,2,3
B. Propanol-1
C. Propanol-2
D. Propanetriol-1
E. Propanediol-1,2,3
ANSWER: A
73. What reagent can be used to distinguish ehandiol-1,2 from ethanol?
A. conc. HNO3 and conc. H2SO4
B. Sodium chloride
C. Cooper hydroxide (II)
D. powder of cooper at the 280-3000С
E. Phosphorus pentachloride
ANSWER: C
74. Choose the formula of methanol homologue:
A. C3H5OH
B. C6H5OH
C. C7H15OH
D. C2H4(OH)2
E. C3H3OH
ANSWER: C
75. Choose the secondary alcohol:
A. 2-butanol
B. 1-butanol
C. 3-methylpentanol-3
D. 2-methylbutanol-2
E. 3-pentanol
ANSWER: A
76. Choose the primary alcohol:
A. 3-methylbutanol-2
B. 2-methylbutanol-2
C. 2-butanol
D. 1-butanol
E. 3-pentanol
ANSWER: D
77. Haw mane hydroxyl groups has glycerol?
A. 1
B. 2
C. 3
D. 4
E. 5
ANSWER: C
78. General formula of saturated alcohols is the following one:
A. CnH2n+1OH
B. CnH2nOH
C. CnH2n+2
D. CnH2n–2OH
E. C2nH2n+2
ANSWER: A
79. Interaction of alcohols with halogenalkanes belongs to the following type of reaction:
Polymerization
Accession
Elimination
Decomposition
Substitution
ANSWER: E
80. Glycerol belongs to:
A. Aldehydes
B. Polyatomic alcohols
C. Carbohydrates
D. Fats
E. Esters
ANSWER: B
81. Choose the chemical formula of propanol:
A. CH3OH
B. C3H7OH
C. C2H5OH
D. C4H9OH
E. C5H9OH
ANSWER: B
82. Ethanol is more easily soluble in:
A. Water
B. Oils
C. Benzene
D. Fats
E. Alkalis
ANSWER: A
83. Qualitative reaction on Glycerol is an interaction with:
A. Calcium hydroxide
B. Cooper (ІІ) oxide
C. Cooper (ІІ) hydroxide
D. Cooper (І) oxide
E. Alkali
ANSWER: C
84. Choose the mechanism of etherification reaction:
A. SN1
B. E1
C. E2
D. SN2
E. S
ANSWER: D
85. Trinitrate glycerol by the chemical nature is:
A. Ester
B. Acid
C. Ether
D. Polyatomic alcohol
E. Alcohol
ANSWER: A
86. Etherification reaction is the interaction between:
A. Alcohol and acid
B. Acid and aldehyde
C. Alcohol and aldehyde
D. Alcohol and alcohol
E. Ketone and aldehyde
ANSWER: D
87. Choose the reaction of ester formation:
A. Interaction of alcohols between each other
A.
B.
C.
D.
E.
Interaction of alcohols with metallic sodium
Interaction of alcohols with carboxylic acids
Interaction of alcohols with halogenalkanes
Interaction of alcohols with alkali
ANSWER: C
88. Choose the reaction of ether formation:
A. Interaction of alcohols with alkali
B. Interaction of alcohols with metallic sodium
C. Interaction of alcohols with carboxylic acids
D. Interaction of alcohols with halogenalkanes
E. Interaction of alcohols between each other
ANSWER: E
89. What compound will react with sodium hydroxide?
A. Propane
B. Benzene
C. Phenol
D. Ethylene
E. Butane
ANSWER: C
90. Reagent for the phenol identification is:
A. Bromine water
B. Potassium permanganate solution
C. Freshly precipitated cooper (ІІ) hydroxide
D. Ammonium solution of silver (І) oxide
E. Chloride acid
ANSWER: A
91. Which type of reaction is most common for alkyl halides?
A. AR (radical addition)
B. nucleophilic addition (AN)
C. electrophilic addition (AE)
D. nucleophilic substitution (SN)
E. electrophilic substitution (SE)
ANSWER: D
92. Formalin is used in medical practice as a disinfectant, conservant for anatomical wet preparations. What
is formalin?
A. 40% water solution of acetic aldehyde
B. 40% water solution of formic aldehyde
C. 40% water solution of benzaldehyde
D. 20% water solution of acetic aldehyde
E. 10% water solution of formic aldehyde
ANSWER: B
93. Aldehydes are the derivatives of hydrocarbons that contain group:
A. phenyl
B. carboxylic
C. carbonyl
D. nitrozoE. nitroANSWER: C
94. The qualitative reaction on aldehyde group is:
A. reaction of reduction
B. reaction with acid fuchsin sulfite
C. Cannizzaro reaction
D. reaction of aldol condensation
E. iodoform test
ANSWER: B
95. Formaldehyde and methanal are:
A. Homologues
B.
C.
D.
E.
Geometric isomers
Structural isomers
The same compounds
Enantiomers
ANSWER: D
96. Formaldehyde and propanal:
A. Homologues
B. Geometric isomers
C. Structural isomers
D. The same compounds
E. Enantiomers
ANSWER: A
97. Ethanal and acetic aldehyde are:
A. Homologues
B. Geometric isomers
C. Structural isomers
D. The same compounds
E. Enantiomers
ANSWER: D
98. What types of reactions are character for methanal?
A. Oxidation and reduction
B. Burning and neutralization
C. Exchange and oxidation
D. Reduction and exchange
E. Exchange and neutralization
ANSWER: A
99. What compound does form after the formaldehyde oxidation by cooper (ІІ) hydroxide?
A. Benzoic acid
B. Butanoic acid
C. Acetic acid
D. Formic acid
E. Salicylic acid
ANSWER: D
100. Organic compound, which is the product of acetylene hydratation, gives “silver mirror” reaction and
at the reduction forms ethanol is:
A. Acetaldehyde
B. Propane
C. Acetic acid
D. Acetone
E. Propanone
ANSWER: A
B.
C.
D.
E.