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Final submodule control I: «The theoretical basis of the structure and reactivity of organiccompounds, aliphatic and aromatic, hydroxy and halogeno hydrocarbons, their thioanalogues and amines."
English. Submodule 1
1. Choose the product of reaction
A. E.
B. D.
C. B.
D. C.
E. *** A.
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2. Myrcene – is a monoterpene contained in bay leaves.
A.
E. 4
B. ***
D. 3*
C.
C. 2
D.
B. 1
E.
A. 0
3. Choose the product of reaction
A. *** E.
B. D.
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C. C.
D. B.
E. A.
4. Choose the product of reaction
A. *** E.
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B. D.
C. C.
D. B.
E. A.
5. Choose the product of reaction
A. E.
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B. *** D.
C. C.
D. B.
E. A.
6. Complete the reaction:
A. E.
B. D.
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C. *** C.
D. B.
E. A.
7. Define the type of marked bond
A. covalent non-polar bond
B. *** covalent polar bond
C. dative bond
D. ionic bond
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E. hydrogen bond
8. Specify the type and charge of the electronic effects of the nitrogen atom in the molecule of the aniline
A. +I
B. +I;+M
C. *** -I;+M
D. -I; -M
E. -I
9. Which class of hydrocarbons reveals acidic properties
A.
A. aklanes
B.
B. alkenes
C.
C. arenes
D.
D. alkadienes
E. *** E. terminal alkynes
10.
Give the most correct nomenclature name (IUPAC) for the following compound:
A. 1,5-dioxohexene-3-ol-2
B. 1-oxo–2–hydroxyhexene-3-one-4
C. 2,6-dioxo-5-hydroxyhexene-3
D. 2-oxo-5-hydroxyhexenal
E. *** 2-hydroxy-5-oxohexene-3-al
11. Furosemide is a strong diuretic:
Specify its senior functional group.
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A. SO NH
B. furan ring
C. secondary amino group
D. *** СООН
E. Cl
12. Select the compound with the strongest basic properties among the next compounds:
A. 2
B. 3
C. 1
D. 5
E. 4
13. Specify the type and charge of the electronic effect of the nitrogen atom in the molecule of benzonitrile
A. *** -I;-M
B. -I
C. -I;+M
D. -M
E. +M
14. There are some five-membered heterocyclic compounds components of the many drugs:
Which of them has the strongest acidic properties.
A. 3
B. *** 5
C. 1
D. 2
E. 4
2 2
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15. Choose the strongest base in the following line of amines:
A. 5
B. *** 3
C. 4
D. 2
E. 1
16. How many chiral centres are present in the following compound?
A. 4
B. 3
C. *** 2
D. 1
E. 0
17. Assign IUPAC name to this carboxylic acid
A. *** 2-Methylpropanoic acid
B. Butanoic acid
C. propanoic acid
D. 2,2-Dimethylpropanoic acid
18. Assign IUPAC name to this carboxylic acid
A. *** 2,2-Dimethylpropanoic acid
B. propanoic acid
C. 2-Methylpropanoic acid
D. Butanoic acid
19. Assign IUPAC name to this carboxylic acid
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A. *** Butanoic acid
B. propanoic acid
C. 2,2-Dimethylpropanoic acid
D. 2-Methylpropanoic acid
20. Assign IUPAC name to this carboxylic acid
A. *** 2-Ethylpentanoic acid
B. 2,2-Dimethylpropanoic acid
C. 2-Methylpropanoic acid
D. propanoic acid
21. Assign IUPAC names to this aldehyde
A. *** 2-Methylpropanal
B. 2,3-Dichlorobutanal
C. 3-hydroxypentanal
D. 3-methylbutanal
22. Assign IUPAC names to this aldehyde
A. *** 2,3-Dichlorobutanal
B. 2-Methylbutanal
C. 3-hydroxypentanal
D. 3-methylbutanal
23. Assign IUPAC names to this aldehyde
A. *** 2-Ethylpentanal
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B. 3-hydroxypentanal
C. 3-methylbutanal
D. 2,3-Dichlorobutanal
24. Assign IUPAC names to this ketone
A. *** 3-Hydroxy-4-methylcyclohexanone
B. 2,4-Dimethyl-3-pentanone
C. 3-bromocyclopentanone
D. 2-methylcyclohexanone
25. Assign numbers from (1) for LEAST to (4) for MOST to indicate the relative acid strengths in the following group: phenol, m-cholorophenol, m-nitrophenol, m-cresol:
A. 2, 3, 4, 1
B. 1, 3, 2, 4
C. 2, 4, 1, 3
D. 4, 1, 2, 3
26. Choose the right order of decreasing basicity:
A. there is no right answer
B.
C.
27. Convert IUPAC name to common names for thiol - 1-Pentanethiol ?
A. *** Pentyl mercaptan
B. sec-Butyl mercaptan
C. tert-Butyl mercaptan
D. Isobutyl mercaptan
28. Convert IUPAC name to common names for thiol - 2-Methyl-2-propanethiol ?
A. Isobutyl mercaptan
B. *** tert-Butyl mercaptan
C. Pentyl mercaptan
D. sec-Butyl mercaptan
29. Convert this common name for thiol to IUPAC name - Methyl mercaptan
A. *** Methanethiol
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B. 1-Pentanethiol
C. 1-propanethiol
D. 2-Methyl-2-propanethiol
30. Identify the starting alcohol from which this product was obtained by an alcohol dehydration reaction?
A. C.
B. B.
C. *** A.
31. Name Dimethyl ether utilizing IUPAC nomenclature rules:
A. *** Methoxymethane
B. 1- Propoxypropane
C. 1- Methoxy-2-methylpropane
D. 1,3 – Dimethoxycyclohexane
32. Name the following compound:
A. p-methoxyethylbenzene
B. p-hydroxyacetanilide
C. *** p-allylphenol
D. sodium acetylsalicylate
E. E.ethoxybenzene
33. Name the following compound
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A. 2-benzoylthiophene
B. *** 3-furansulfonic acid
C. disulfopyrrole
D. 3-benzoylthiophene
E. 2-methylthiophene
34. Name this ether utilizing IUPAC nomenclature rules:
A. *** 1,3 – Dimethoxycyclohexane
B. 1- Methoxy-2-methylpropane
C. Methoxymethane
D. 1- Propoxypropane
35. Select the compound with the strongest acidic properties among the next compounds:
A.
B.
C.
D. ***
E.
36. Select the compound with the strongest acidic properties among the next compounds:
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A.
B.
C. ***
D.
37. Select the compound with the strongest basic properties among the next compounds:
A.
B.
C.
D.
E. ***
38. Select the compound with the strongest basic properties among the next compounds:
A.
B.
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C.
D. ***
E.
39. Select the compound with the strongest basic properties among the next compounds:
A.
B. ***
C.
D.
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E.
40. Select the compound with the strongest basic properties among the next compounds:
A.
B.
C.
D.
E. ***
41. What IUPAC name has this aldehyde?
A. *** 2-Methylbutanal
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B. 3-hydroxypentanal
C. 3-methylbutanal
D. 2,3-Dichlorobutanal
42. What IUPAC name has this common name for thiol - sec-Butyl mercaptan ?
A. *** 2-Butanethiol
B. 1-propanethiol
C. 2-Methyl-2-propanethiol
D. 1-Butanethiol
43. What keton has this IUPAC name - 2,4-Dimethyl-3-pentanone?
A.
B.
C.
D. ***
44. What keton has this IUPAC name - Cyclobutanone?
A.
B. ***
C.
D.
45. Write the structure for 1-ethyl-5-bromo-2-pyrrolecarboxylic acid:
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A.
B. ***
C.
D.
E.
46. Write the structure for 2,4-dimethylfuran:
A.
B.
C. ***
D.
E.
47. Choose a compound with strongest basic properties:
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A. 1
B. 2
C. *** 3
D. 4
E. 5
48. Choose a compound with strongest basic properties:
A. 5
B. 4
C. 3
D. 2
E. *** 1
49. Choose at least strong base of the following
A. ***
B.
C.
D.
50. Choose the most correct systematic name for mercazolyl.
A. 1-Methyl-2-thiopyrazol.
B. 2-Mercapto-3-methylimidazole.
C. 1-Methyl-2-thiopyrrole.
D. *** 1-Methyl-2-mercaptoimidazole.
E. 1-Methyl-2-mercaptopyrazole.
51. Choose the product of reaction
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A. E.
B. D.
C. *** C.
D. B.
E. A.
52. Choose the strongest base in the following line of amines:
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A. *** 1
B. 2
C. 3
D. 4
E. 5
53. Choose the strongest base of the following
A.
B. ***
C.
D.
54. Choose the type of reaction which is typical for alkanes
A.
A. S
B.
B. S
C. ***
C. S
D. D. A
E.
E. A
55. Choose the type of reaction which is typical for alkenes
A.
A. S
B.
B. S
C.
C. S
D. ***
D. A
E. ***
E. A
56. Choose the type of reaction which is typical for alkynes
N
E
R*
E
N
N
E
N
E
N
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A.
A. S
B.
B. S
C.
C. S
D.
D. A
E.
E. A
57. Choose the type of reaction which is typical for arenes
A.
A. S
B.
B. S
C.
C. S
D.
D. A
E.
E. A
58. Cinnamic acid – is found in cinnamon oil and balsams such as storax. Choose reagents for quality analysis of double bond in molecule.
A. H O
B. ZnCl ; Cl
C. HBr
D. FeCl ; O
E. *** KMnO
59. Classify antibacterial remedystreptocid:
N
E
N
E
N
N
E
N
E
N
2 2
2 2
3 3
4
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A. *** Amide of aromatic sulfonic acid
B. Aromatic acid
C. Aromatic sulfonic acid
D. Carbocyclic amine
E. Aromatic amine
60. Complete the reaction:
A. E.
B. D.
C. C.
D. A.
E. *** B.
61. Complete the reaction:
A. E.
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B. D.
C. *** B.
D. C.
E. A.
62. Complete the reaction:
A. E.
B. D.
C. *** C.
D. B.
E. A.
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63. Complete the reaction:
A. B.
B. *** A.
C. C.
D. D.
E. E.
64. Complite the reaction:
A. E.
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B. *** C.
C. D.
D. B.
E. A.
65. Complite the reaction:
A. *** E.
B. D.
C. B.
D. C.
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E. A.
66. Decide just by the name which of the following compounds surely rotate plane polarized light clockwisely
A. Ethanol
B. D-glucose
C. *** (+)-phenylalanine
D. racemic glutamic acid
E. L-phenylalanine
67. Define the type of electronic effects of halogen atom in the molecule of benzyl chloride:
A. *** -I
B. -I;-M
C. -I;+M
D. +I
E. +I;+M
68. Define the type of electronic effects of hydroxyl in the molecule of salicylic acid:
A. +I
B. +M
C. -I
D. *** -I;+M
69. Define the type of hybridization for marked carbon atoms.
A. sp-hybrid
B. *** sp -hybrid
C. sp -hybrid
2
3
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70. Define the type of hybridization for marked carbon atoms.
A. sp-hybrid
B. sp -hybrid
C. *** sp -hybrid
71. Define the type of hybridization for marked carbon atoms.
A. *** sp -hybrid
B. sp -hybrid
C. sp-hybrid
72. Define the type of hybridization for marked carbon atoms.
A. sp-hybrid
B. *** sp -hybrid
C. sp -hybrid
73. Define the type of hybridization for marked carbon atoms.
A. *** sp -hybrid
B. sp -hybrid
C. sp-hybrid
74. Define the type of hybridization for marked carbon atoms.
2
3
2
3
2
3
2
3
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A. sp-hybrid
B. *** sp -hybrid
C. sp -hybrid
75. Define the type of hybridization for marked carbon atoms.
A. *** sp-hybrid
B. sp -hybrid
C. sp -hybrid
76. Define the type of hybridization for marked carbon atoms.
A. *** sp-hybrid
B. sp -hybrid
C. sp -hybrid
77. Define the type of hybridization for marked carbon atoms.
A. sp-hybrid
B. sp -hybrid
C. *** sp -hybrid
78. Define the type of hybridization for marked carbon atoms.
A. sp-hybrid
2
3
2
3
2
3
2
3
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B. sp -hybrid
C. *** sp -hybrid
79. Define the type of hybridization for marked carbon atoms.
A. sp-hybrid
B. *** sp -hybrid
C. sp -hybrid
80. Define the type of hybridization for marked carbon atoms.
A. sp-hybrid
B. sp -hybrid
C. *** sp -hybrid
81. Define the type of marked bond
A. ionic bond
B. hydrogen bond
C. *** covalent non-polar bond
D. covalent polar bond
E. dative bond
82. Define the type of marked bond
2
3
2
3
2
3
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A. covalent non-polar bond
B. *** covalent polar bond
C. dative bond
D. ionic bond
E. hydrogen bond
83. Define the type of marked bond
A. covalent non-polar bond
B. *** covalent polar bond
C. dative bond
D. ionic bond
E. hydrogen bond
84. Define the type of marked bond
A. hydrogen bond
B. covalent non-polar bond
C. *** covalent polar bond
D. dative bond
E. ionic bond
85. Define the type of marked bond
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A. hydrogen bond
B. *** covalent non-polar bond
C. covalent polar bond
D. dative bond
E. ionic bond
86. Define the type of marked bond
A. covalent non-polar bond
B. covalent polar bond
C. *** dative bond
D. ionic bond
E. hydrogen bond
87. Define the type of marked bond
A. covalent non-polar bond
B. covalent polar bond
C. dative bond
D. ionic bond
E. *** hydrogen bond
88. Define the type of marked bond
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A. covalent non-polar bond
B. covalent polar bond
C. dative bond
D. ionic bond
E. *** hydrogen bond
89. Ethynyl estradiol diacetate— is a synthetic steroid. Choose reagent, which we can use to find out triple bond in molecule.
A. FeCl
B. I (KOH)
C. K Cr O
D. [Ag(NH ) ]OH
E. *** Br
90. How many asymmetrical carbon atoms are present in a molecule of epinephrine?
A. 4
B. 3
C. 2
D. 0
E. *** 1
91. How many enantiomers could propranolol have?
A. 0
B. 1
3
2
2 2 7
3 2
2
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C. *** 2
D. 3
E. 4
92. Indicate the type and sign of electronic effects of the oxygen atom in the molecule of furan:
A. -I
B. +I
C. -M
D. +M
E. *** -I;+M
93. Mark optimal reagent to conduct the next reaction:
A. Cl
B. *** SOCl
C. HCl
D. KCl
E. CH –Cl
94. Name the following phenol by the IUPAC system:
A. A.hydroxybenzene
B. *** B.1,4-dihydroxybenzene
C. C.Resorcinol
D. Hydroquinone
95. Name the next structure
A. 3-(N-methylamino)-1-propanol
B. *** ethyl 3-(N-methylamino)-2-butenoate
C. 2-N,N-dimethylaminobutane
D. allylamine
96. Name the substance in accordance with its structure:
2
2
3
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A. 3,3-dimethyl-2-hexanone
B. *** 2,3,5-triethylcyclohexanone
C. methyl propyl ketone
D. m-ethylacetophenone
E. 2,4,5-triethylcyclohexanone
97. Name this amin utilizing IUPAC nomenclature rules:
A. nitrianiline
B. aniline
C. benzenamine
D. *** Cyclohexanamine
E. oxime
98. Name this amin:
A. dimethylamine
B. methylisopropylamine
C. *** N-methyl-m-toluidine
D. trimethylanilinium
E. t-butylamine
99. p-Aminobenzoic acid – Carbolic acid, synthon for analgesics: Mark directing influence of the COOH-group in S reactions:
A. *** activator о-, p-directing
B. deactivator о-, p-directing
C. activator m-directing
E
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D. deactivator m-directing
E. activator о-, m-directing
100. Specify the type and charge of the electronic effect of the oxygen atom in a molecule of sodium ethoxide:
A. -I
B. *** +I
C. -M
D. +M
E. -I;+M
101. Specify the type and charge of the electronic effect of the oxygen in the molecule of 2-propanol:
A. *** -I
B. +I
C. -M
D. +M
E. -I;+M
102. Specify the type and charge of the electronic effects of the oxygen atom of the carbonyl group in the molecule of acetophenone:
A. -I
B. *** -I;-M
C. -I;+M
D. +I
E. +I;+M
103. What types of atoms are present in alkanes with unbranched chain of carbon atoms?
A.
A. Primary
B.
B. Secondary
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C.
C. Tertiary
D. D. Fourtary
E. *** E. Primary and secondary
104. Which functional group is in the carboxylic acids?
A. Carbonyl group
B. *** Carboxyl group
C. Nitro group
D. Phenyl group
E. Sulfo group
105. Which of following benzene heterofunctional derivatives is the most active in the S :
A. A. 1
B. B. 2
C. C. 3
D. *** D. 4
E. E. 5
E
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