Characteristic chemical properties of hydrocarbons: alkanes, alkenes, dienes, alkynes.Mechanisms of substitution and addition reactions in organic chemistry. Rule V.V. Markovnikova.
1. Both benzene and styrene are characterized by
1) the presence in the molecule of a conjugated electronic system
2) sp 3 -hybridization of carbon atoms
3) interaction with hydrogen in the presence of a catalyst
4) discoloration of bromine water
5) flammability
2. Both toluene and benzene react with
1) bromine
2) chloromethane
4) hydrogen bromide
5) nitric acid
6) copper hydroxide( II)
3. Potassium permanganate solution is decolorized
1) pentane
2) benzene
3) butine-1
4) toluene
5) penten-2
6) polyethylene
4. Bromine water is decolorized
1) pentane
2) benzene
3) butine-1
4) toluene
5) butene-2
6) butadiene-1,3
5. Both toluene and butadiene-1,3 are characterized by
1) the presence of a conjugated electron system in a molecule
2) sp 2 - hybridization of all carbon atoms
3) substitution reactions
4) discoloration of the CM solution nO 4
5) flammability
6) good solubility in water
6. Toluene reacts with
1) ammonia
2) hydrogen chloride
3) chlorine under light
4) ammonia solution silver oxide
5) chlorine in the presence of a catalyst AICI3
6) chloroethane in the presence of a catalyst AICI3
7. Propyne interacts with
1) sodium
2) bromine water
3) methane
4) nitrogen
5) sodium hydroxide
8. Propene interacts with
1) sodium
2) bromine water
3) methane
4) hydrogen bromide
5) sodium hydroxide
6) water in the presence of a catalyst
9. Butane reacts
1) hydration
2) hydrogenation
3) bromination
4) dehydration
5) isomerization
6) dehydrogenation
10. By ionic mechanism reactions occur whose equations are:
1) CH 4 + O 2 -- > C O 2 + 2H 2 O
2) CH 2 = CH 2 + HC1 --> CH 3 -CH 2 C1
4) C 2 H 6 + Cl 2 --> C 2 H 5 Cl + HCl
5) CH 3 -CH = CH 2 + HB r --> CH 3 -CHBg-CH 3
6) CH 3 - CH = CH 2 + H 2 --> CH 3 - CH 2 - CH 3
11. Methods for producing alkenes include:
1) dehydrogenation of alkanes
2) hydrogenation of benzene
3) dehydration of alcohols
4) elimination of hydrogen halides from haloalkanes
5) aromatization of saturated carbons
6) hydration of aldehydes
12. Both methane and propene are characterized by:
1) bromination reactions
2) sp 3
3) presence of p - bonds in molecules
4) hydrogenation reactions
5) combustion in air
6) good solubility in water
13. Propyne will react with each of the substances indicated in the series:
1) OH, H 2 O, H 2
2) CuSO 4, C, Br 2
3) Na 2 O, HCI, O 2
4) OH
2) Br 2 (solution)
3) C u (OH) 2
4) KM nO 4 (solution)
5) H 2 O (H + )
6) Ca(OH) 2
15. Methane is characterized by:
1) hydrogenation reaction
2) tetrahedral shape of the molecule
3) presence of p -bonds in a molecule
4) sp 3 - hybridization of the orbitals of a carbon atom in a molecule
5) reactions with hydrogen halides
6) combustion in air
16. Of the following compounds react with hydrogen chloride
1) ethane
2) ethylene
3) benzene
4) glycine
5) formic acid
6)a -aminopropionic acid
17. Hydrocarbons of the ethylene series will react with each of the substances indicated in the series:
1) Br 2, HCI, C 3 H 8
2) KM nO 4, H 2, H 2 O
3) H С l, C 6 H 6, Br 2
4) HCNO, CH 4, NVg
5) H 2, O 2, N a
6) H 2 O, HCI, Br 2
18. Each of two substances interacts with hydrogen:
1) benzene, propane
2) butene, ethane
3) divinyl, ethene
4) styrene, butadiene-1,3
5) dichloroethane, butane
6) ethin, butine-1
19. Acetylene can be obtained as a result of the reaction
1) carbon hydrogenation
2) hydrolysis of aluminum carbide
3) hydrolysis of calcium carbide
4) interactions Na 2 C 2 with acid
5) methane pyrolysis
6) ethanol dehydration
20. Intermediate formation of carbocation CH 3 - CH + - CH 3
1) propane and chlorine
2) propene and chlorine
3) propene and hydrogen chloride
4) propene and water in the presence of a catalyst
5) propyne and hydrogen chloride
6) propene and hydrogen bromide
21. Reactions proceed according to the radical mechanism
1) CH 4 + C1 2 --> CH 3 C1 + HC1
2) C 2 H 4 + H 2 O --> C 2 H 5 OH
3) C 2 H 6 + HNO 3 --> C 2 H 5 N0 2 + H 2 0
4) C 2 H 2 + H 2 O --> CH3CHO
5) C 2 H 6 + Br 2 -->C 2 H 5 Br + HBr
6) C 2 H 5 OH + HBr --> C 2 H 5 Br + H 2 0
22. Intermediate formation of carbocation CH 3 - CH + - CH 2 - CH 3 occurs during interaction
1) butane and bromine
2) butene-2 and bromine
3) butene-1 and hydrogen chloride
4) butene-2 and hydrogen chloride
5) butene-1 and water
6) butene-2 and hydrogen
23. The propane bromination reaction proceeds
1) by radical mechanism
2) in several stages
3) with the cleavage of the bond in the bromine molecule at the beginning of the reaction
4) in accordance with the rule of V.V. Markovnikova
5) in the presence of a catalyst
6) with the predominant formation of 1-bromopropane
24. Ethylene is produced as a result of reactions
1) ethanol dehydration
2) ethanol recovery
3) hydrogenation of ethyl
4) thermal decomposition acetylene
5) ethane dehydrogenation
6) hydrolysis of ethylbenzene
25. Butane is characterized by:
1) the presence of structural isomers
2) geometric isomerism
3) sp 3 - carbon atom hybridization
4) presence of s - and p -bonds in molecules
5) reactions with halogens
6) oxidation with potassium permanganate
26. The polymerization reaction is characteristic of
1) styrene
2) 2-methylbutadiene-1,3
3) 2-methylpropane
4) tetrafluoroethene
5) 2-methylbutane
6) 3-methylpentane
27. Bromine water becomes discolored when exposed to
1) acetylene
2) propane
3) butadiene-1,3
4) benzene
5) styrene
6) 2,2-dimethylpropane
28. Propane is characterized by
1) combustion
2) structural isomerism
3) sp 3 -hybridization of carbon atoms in a molecule
4) geometric isomerism
5) substitution reactions
6) interaction with bromine water
29. According to the rule of V.V. Markovnikov interaction occurs
1) butene-1 and hydrogen chloride
2) propene and water
3) butene-1 and chlorine
4) butene-1 and hydrogen
5) butene-2 and bromine
6) propene and hydrogen chloride
30. Carbon atoms are in the state sp 3 - hybridizations are present in molecules
1) 2-chlorobutane
2) divinyl
3) isobutane
4) etina
5) propina
6) vinylbenzene
31. Carbon atoms are in the state sp 2 - hybridizations are found in molecules
1) butane
2) cis-butene-2
3) trans-butene-2
4) methanol
5) acetylene
6) toluene
ANSWERS: 1-135; 2-125; 3-345; 4-356; 5-145; 6-356; 7-126; 8-246; 9-356; 10-235; 11-134; 12-125; 13-146; 14-245; 15-246; 16-246; 17-236; 18-346; 19-345; 20-346; 21-135; 22-345; 23-123; 24-135; 25-135; 26-124; 27-135; 28-135, 29-126, 30-135, 31-236.
Task 1. What chemical reactions can be used to remove propene impurities from propane?
Solution . Propene can be absorbed with bromine water:
CH 3 -CH = CH 2 + Br 2 → CH 3 -CHBr-CH 2 Br
or aqueous solution potassium permanganate:
CH 3 -CH = CH 2 + [O] + H 2 O → CH 3 -CH (OH) -CH 2 OH.
Propane does not react with these substances and evaporates.
Task 2. Ethylene hydrocarbon weighing 7.0 g adds 2.24 l (no.) of hydrogen bromide. Determine the molar mass and structure of this hydrocarbon if it is known to be a cis isomer.
Solution . Ethylene hydrocarbons add hydrogen bromide according to the equation:
C n H 2n + HBr → C n H 2n+1 Br.
v(HBr) = 2.24/22.4 = 0.1 mol. v(C n H 2n) = v(HBr) = 0.1 mol. M (C n H 2 n ) = 7.0/0.1 = 70 g/mol, therefore, n = 5. There are 5 structural isomers of ethylene hydrocarbons with the composition C 5 H 10:
CH 3 -CH 2 -CH 2 -CH=CH 2 CH 3 -CH 2 -CH=CH-CH 3
penten-1 penten-2
2-methylbutene-1 2-methylbutene-2 3-methylbutene-1
Of these substances, only pentene-2 has cis-trans nsomers:
trans-pentene-2 cis-pentene-2
Answer . Cis-pentene-2.
Task 3. How many individual substances of the composition C 3 H 5 Cl exist? decolorizing bromine water? Bring structural formulas molecules of these substances.
Solution . C 3 H 5 Cl is a monochlor derivative of the hydrocarbon C 3 H 6. This substance discolors bromine water, therefore, it contains a double bond. Three carbon atoms can only form a straight carbon skeleton with a terminal double bond:
Structural isomerism is possible only due to the position of the chlorine atom relative to double bond:
CH 3 -CH = CHCl CH 3 -CCl = CH 2 Cl -CH 2 -CH = CH 2
1-chloropropene 2-chloropropene 3-chloropropene
1-chloropropene can exist in the form of cis-trans isomers: 
trans-1 –chloropropene cis -1-chloropropene
Answer . 4 isomers.
Task 4. When 11.2 l (n.s.) of a mixture of isomeric hydrocarbons, which are gases with a hydrogen density of 21, reacted with bromine water, 40.4 g of the corresponding dibromo derivative was obtained. Determine the structure of these hydrocarbons and the content of each of them in the mixture (in % by volume).
Solution . Molar mass isomeric hydrocarbons is equal to: M (C x H y) = 21 * 2 = 42 g/mol, therefore, hydrocarbons have the formula C 3 H 6. Two substances have this molecular formula: propene and cyclopropane. Propene reacts with bromine water:
CH 3 - CH = CH 2 + Br 2 → CH 3 - CHBr - CH 2 Br.
The molar mass of the dibromo derivative is: M(C 3 H 6 Br 2) = 202 g/mol, and its quantity: v (C 3 H 6 Br 2) = 40.4/202 = 0.2 mol. Therefore, the initial mixture contained 0.2 mol of propene. The total amount of hydrocarbons in the mixture was 11.2/22.4 = 0.5 mol; the remaining 0.3 mol comes from cyclopropane, which does not react with bromine water.
The volume fractions of gases in the mixture are equal to their mole fractions: j (propene) = 0.2/0.5 = 0.4, or 40%, j (cyclopropane) = 0.6, or 60%,
Answer . 40% propene, 60% cyclopropane.
Task 5. When the alkene was passed through an excess solution of potassium permanganate, the mass of the precipitate formed was 2.07 times more mass alkene. Determine the formula of the alkene.
Solution . Alkenes are oxidized with an aqueous solution of potassium permanganate according to the general equation:
ZS n H 2 n + 2K Mn O 4 + 4H 2 O = 3C n H 2 n (OH) 2 + 2MnO 2 ↓ + 2 KOH/>.
From 3 moles of an alkene (with a mass of 3-(12n +2n) = 42n) 2 moles of Mn O 2 are formed (with a mass of 2 * 87 = 174 g). According to the conditions of the problem
42n –2.07= 174,
whence n = 2. The desired alkene is ethylene. C 2 H 4 .
Answer . C 2 H 4 .
Characteristic chemical properties of hydrocarbons: alkanes, alkenes, dienes, alkynes. Characteristic chemical properties of aromatic hydrocarbons (benzene and toluene).
1. When alkenes are hydrogenated, they form
1) alkanes 2) alkynes 3) alkadienes 4) alcohols
2. When 1 mole of propyne reacts with 2 moles of chlorine,
1) 1,1-dichloropropane
2) 1,2-dichloropropane
3) 1,1,2-trichloropropane
4) 1,1,2,2-tetrachloropropane
3. The presence of a double bond determines the ability of alkenes to react
1) combustion
2) replacement of hydrogen with halogen
3) dehydrogenation
4) polymerization
4. When 1 mol CH 4 interacts with 2 mol Cl 2 under illumination, the result is predominantly
1) chloromethane 2) dichloromethane 3) chloroform 4) tetrachloroethane
5. Addition reactions are typical for
1) alkanes
2) saturated monobasic carboxylic acids
3) phenols
4) alkynes
6. AMONG THE PRODUCTS OF NITRATION OF 2-METHYLBUTANE ACCORDING TO M.I.KONOVALOV WILL PREVAIL
1) 3-nitro-2-methylbutane 3) 2-nitro-2-methylbutane
2) 1-nitro-2-methylbutane 4) 1-nitro-3-methylbutane
7. REACTION LEADING TO CHAIN TERMINATION DURING METHANE BROMATION
1) Br 2 Br + + Br
2) Br + CH 4 –>CH 3 + HBr
3) CH 3 + Br –> CH 3 Br
4) CH 3 + Br 2 –> CH 3 Br + Br
8. Can react with each of the substances: water, hydrogen bromide, hydrogen
2) chloromethane
9. Both butane and butylene react with
1) bromine water
2) an aqueous solution of potassium permanganate
3) hydrogen
10. The product of the reaction of propene with chlorine is
1) 1,2-dichloropropene
2) 2-chloropropene
3) 2-chloropropane
4) 1,2-dichloropropane
11. The product of the reaction of butene-1 with chlorine is
1) 2-chlorobutene-1
2) 1,2-dichlorobutane
3) 1,2-dichlorobutene-1
4) 1,1-dichlorobutane
12. The conversion of butane to butene refers to the reaction
1) polymerization
2) dehydrogenation
3) dehydration
4) isomerization
13. When alkenes are hydrogenated, they form
3) alkadienes
14. Butane as opposed to butene-2
1) reacts with oxygen
2) does not undergo hydrogenation reaction
3) does not react with chlorine
4) has a structural isomer
15. Among cycloalkanes, the most reactive is
1) cyclobutane
2) cyclopropane
3) cyclopentane
4) cyclohexane
16. 1-PENTENE AND 1-PENTINE CAN BE DISTINGUISHED BY ACTION
1) bromine water 3) ammonia solution of silver oxide
2) phenolphthalein 4) potassium permanganate solution
17. The hydrogenation reaction is impossible for
1) cis-butene-2 2) trans-butene-2
3) butene-1 4) butane
18. INTERACT WITH POTASSIUM PERMANGANATE IN SOLUTION
1) propyne, propene, propane 3) 2-butyne, 2-butene, 1,3-butadiene
2) ethane, ethene, acetylene 4) ethyn, 1-pentene, pentane
19. Discoloration of bromine water will not occur when exposed to
20. Both butane and butylene react with
21. The product of the reaction of propene with chlorine is
22. The product of the reaction of butene-1 with chlorine is
23. When alkenes are hydrogenated, they form
24. 2-chlorobutane is mainly formed by the reaction
1) butene-1 and chlorine
2) butene-1 and hydrogen chloride
3) butene-2 and chlorine
4) butin-2 and hydrogen chloride
25. Potassium permanganate solution does not discolor
3) butadiene-1,3
4) 1,2-dimethylbenzene
26.. Methane reacts
1) with hydrogen chloride
2) with water vapor on the catalyst
3) isomerization
4) with bromine water
27. Benzene reacts with
1) bromine water
2) hydrogen chloride
3) ethanol
4) nitric acid
30. When bromine acts on butene-2, it forms
1) 1-bromobutane
2) 2-bromobutane
3) 1,2-dibromobutane
4) 2,3-dibromobutane
32. The reaction is not typical for alkanes
1) isomerization
2) accessions
3) radical substitution
4) combustion
33. Ethylene hydrocarbons can be distinguished from alkanes using
1) bromine water
2) copper spiral
3) ethanol
4) litmus
34. The polymerization reaction involves
4) 1,2-dimethylbenzene
35. Does not undergo polymerization reaction
1) isoprene
3) propylene
36. Does not burn when ignited in air
3) carbon tetrachloride
4) 2-methylpropane
37. When 2-methylbutene-2 reacts with hydrogen bromide, it predominantly forms
1) 2-bromo-2-methylbutane
2) 1-bromo-2-methylbutane
3) 2,3-dibromo-2-methylbuta
4) 2-bromo-3-methylbutane
38. Which substance undergoes a hydration reaction in accordance with Markovnikov’s rule?
1)CH 3 – CH = CH 2
2) CF 3 - CH = CH 2
3) CH 2 = CH – CHO
4) CH 2 = CH – COOH
39. When 1-butene reacts with hydrogen bromide, hydrogen attaches to the carbon atom whose number
40. Contrary to Markovnikova’s rule, she adds water
1) 3,3,3-triflutopropene
2) 3,3-dimethylbutene-1
3) 2-methylpropene
41. The addition of hydrogen bromide is possible for
1) cyclopropane
2) propane
3) benzene
4) hexane
42. Both benzene and toluene react with
1) solution of KMnO 4 (H 2 SO 4 conc.)
2) bromine water
3) nitric acid (H 2 SO 4 conc)
4) hydrochloric acid
43. Propane can be distinguished from propene using
1) copper (II) hydroxide
2) ethanol
3) litmum solution
4) bromine water
44. 2-chloropropane is predominantly formed as a result of the interaction of hydrogen chloride with
1) propane
2) propene
3) propanol-1
4) propyne
45. 1-BUTENE DOES NOT INTERACT WITH
1) chlorine 3) bromine water
2) hydrogen 4) ammonia solution of silver oxide
46. Benzene undergoes a substitution reaction with
1) bromine and nitric acid
2) oxygen and sulfuric acid
3) chlorine and hydrogen
4) nitric acid and hydrogen
47. SUBSTANCE THAT DECOLORIZES KMnO 4 SOLUTION
1) cyclohexane
48. Discoloration of bromine water will not occur when exposed to
1) hexene 2) hexane 3) butene 4) propine
49. The monomer for producing polyvinyl chloride is
1) chloroethane
2) chloroethene
3) chloropropane
4) 1,2-dichloroethane
50. The hydrogenation reaction is impossible for
1) cis-butene-2
2) trans-butene-2
3) butene-1
51. Vinyl chloride CH 2 = CH - Cl is formed by the interaction of hydrogen chloride with
1) ethane 2) ethene 3) ethyne 4) ethanediol
52. The addition reaction is characteristic of each of the two substances
1) butene-1 and ethane
2) ethyne and cyclopropane
3) benzene and propanol
4) methane and butadiene-1,3
Answers: 1-1, 2-4, 3-4, 4-2, 5-4, 6-3, 7-3, 8-4, 9-4, 10-4, 11-2, 12-2, 13-1, 14-2, 15-2, 16-3, 17-4, 18-3, 19-1, 20-4, 21-4,22-2, 23-1, 24-2, 25- 1, 26-1, 27-4, 28-3, 29-1, 30-4, 31-4, 32-2, 33-1, 34-2, 35-4, 36-3, 37-1, 38-1, 39– 1, 40-1, 41-1, 42-3, 43-4, 44-2, 45-4, 46-1, 47-3, 48-2, 49-2, 50- 4, 51-3, 52-2.
