Task No. 1
Choose two statements that are true for acetylene
1) all carbon atoms are in the state sp 2-hybridization
2) has structural isomers
3) is an unsaturated hydrocarbon
4) highly soluble in water
5) under normal conditions it is a gas
Answer: 35
Task No. 2
Choose two statements that are true for alkynes
1) are saturated hydrocarbons
2) enter into addition reactions
3) can exist in the form cis-, trance- isomers
5) decolorize bromine water
Answer: 25
Task No. 3
1) have general formula CnH2n
2) carbon atoms in molecules are connected to each other only by σ bonds
3) react with sodium
4) react with bromine
5) can be obtained from dihaloalkanes
Answer: 45
Task No. 4
Choose two statements that are true for etin
1) poorly soluble in water
2) has interclass isomers
3) is the main component natural gas
4) can be obtained by hydrolysis of calcium carbide
5) the molecule has a tetrahedral structure
Answer: 14
Task No. 5
Choose two statements that are true for propyne.
1) undergoes a substitution reaction without breaking the triple bond
2) upon trimerization it forms 1,3,5-trimethylbenzene
3) can be obtained by hydrolysis of aluminum carbide
4) is a liquid under normal conditions
5) do not discolor the aqueous solution of potassium permanganate
Answer: 12
Task No. 6
Choose two statements that are true for butine -1
1) undergoes substitution reactions with OH
2) in the hydration reaction it forms butanol-2
3) formed during the dehydrogenation of butane
4) reacts with bromine water
5) is an isomer of isoprene
Answer: 14
Task No. 7
Select two statements that are true for butine-1.
1) does not react with water
2) enters into substitution reactions with Cl
3) upon hydration forms an aldehyde
4) is an isomer of divinyl
5) is able to add only 1 mole of hydrogen
Answer: 24
Task No. 8
Choose two statements that are true for both butine-1 and butine-2.
1) 1 mole of hydrocarbon during hydration can add only 1 mole of water
2) are liquids under normal conditions
3) enter into substitution reactions with an ammonia solution of silver oxide
4) among the products of the reaction with an acidified solution of KMnO 4 there are carboxylic acids
5) can be obtained from 2-chlorobutane in one stage
Answer: 14
Task No. 9
Choose two statements that are true for butine-1 and butine-2.
1) upon hydration they form the same substance
2) molecules have a flat structure
3) can be obtained from 1,1-dibromobutane and 2,3-dibromobutane, respectively
4) undergo substitution reactions with sodium
5) can exist in the form cis-, trance-isomers
Answer: 13
Task No. 10
Choose two statements that are true for all alkynes.
1) discoloration of bromine water
2) react with an ammonia solution of silver oxide
3) the presence of structural isomers
4) highly soluble in water
5) have the general formula of the homologous series C n H 2n-2
Answer: 15
Task No. 11
Choose two statements that are true for all alkynes.
1) molecules have a flat structure
2) all carbon atoms in molecules are connected by π bonds
3) belong to unsaturated hydrocarbons
4) enter into dehydration reactions
5) poorly soluble in water
Answer: 35
Task No. 12
Choose two statements that Not valid for alkynes.
1) can exist in the form cis-, trance- isomers
2) burn in air
4) enter into hydrogenation reactions
5) when interacting with an aqueous solution of potassium permanganate, they form glycols
Answer: 15
Task No. 13
Choose two statements that are true for both ethylene and acetylene.
1) belong to the class of alkenes
2) under normal conditions they are gases
3) decolorize bromine water
5) have the general formula of the homological series C n H 2 n
Answer: 23
Task No. 14
Choose two statements that are true for both ethane and acetylene
1) decolorize an aqueous solution of potassium permanganate
2) poorly soluble in water
3) form explosive mixtures with air
Task No. 15
Choose two statements that are true for both propane and propyne.
1) enter into hydration reactions
2) capable of oxidation by oxygen
3) have interclass isomers
4) react with bromine
5) all carbon atoms in molecules are in the state sp 3-hybridization
Answer: 24
Task No. 24
From the proposed list, select two substances that are structural isomers of pentin-2.
1) 3-methylbutine-1
2) pentin-1
3) 3-methylpentine-1
Answer: 41
Task No. 51
acetylene X Y
1) 1,2-dichloroethane
4) acetaldehyde
5) 1,1-dichloroethane
Answer: 53
Task No. 52
The following scheme of substance transformations is presented:
calcium carbide X Y
Determine which of the following substances are substances X and Y
5) HC≡C― HC=CH 2
Answer: 34
Task No. 53
The following scheme of substance transformations is presented:
sodium acetylenide acetylene Y
1) hydrogen
2) 1,3,5-trimethylbenzene
4) hydrogen bromide
5) chloromethane
Answer: 43
Task No. 54
The following scheme of substance transformations is presented:
NaC≡C-CH 3 X potassium acetate
Determine which of the following substances are substances X and Y
2) KMnO 4 (H 2 SO 4)
3) HC≡C-CH 2 -CH 3
4) H 3 C-C≡C-CH 3
Answer: 45
Alkynes. Compliance tasks.
Task No. 1
Match the name of the substance with the class/group of organic compounds to which this substance belongs:
| A | B | IN | G |
Answer: 2134
Task No. 2
Write down the selected numbers in the table under the corresponding letters.
| A | B | IN | G |
Answer: 5335
Task No. 3
Establish a correspondence between the formulas of substances and the reagent with which they can be distinguished: for each position indicated by a letter, select the corresponding position indicated by a number
Write down the selected numbers in the table under the corresponding letters.
| A | B | IN | G |
Answer: 3434
Task No. 4
Establish a correspondence between the formula of a hydrocarbon and the main product of its interaction with hydrogen chloride at a molar ratio of 1:1: for each position indicated by a letter, select the corresponding position indicated by a number.
Write down the selected numbers in the table under the corresponding letters.
| A | B | IN | G |
Answer: 4612
Task No. 5
Establish a correspondence between the formula of an alkyne and the main product of its reaction with excess hydrogen bromide: for each position indicated by a letter, select the corresponding position indicated by a number.
Write down the selected numbers in the table under the corresponding letters.
| A | B | IN | G |
Answer: 4561
Task No. 6
Establish a correspondence between the name of the alkyne and the product of its reaction with water: for each position indicated by a letter, select the corresponding position indicated by a number.
Write down the selected numbers in the table under the corresponding letters.
| A | B | IN | G |
Answer: 6433
Task No. 7
Establish a correspondence between the name of an organic substance and the product of its interaction with alcohol solution of alkali : For each position indicated by a letter, select the corresponding position indicated by a number.
Write down the selected numbers in the table under the corresponding letters.
| A | B | IN | G |
Answer: 6153
Task No. 8
Establish a correspondence between a dihaloalkane and the product of its interaction with alcohol solution of alkali : For each position indicated by a letter, select the corresponding position indicated by a number.
| REAGENTS | PRODUCT INTERACTION |
| A) 1,2-dichloroethane |
1. Pentin-1 reacts with an ammonia solution of silver oxide (a precipitate forms):
HCºС-CH 2 -CH 2 -CH 3 + OH → AgСºС-CH 2 -CH 2 -CH 3 + 2NH 3 +H 2 O
2. Cyclopentene decolorizes bromine water:
3. Cyclopentane does not react with either bromine water or an ammonia solution of silver oxide.
Example 3. Five numbered test tubes contain hexene, formic acid methyl ester, ethanol, acetic acid, and an aqueous solution of phenol.
It has been established that when metallic sodium acts on substances, gas is released from test tubes 2, 4, 5. Substances from test tubes 3, 5 react with bromine water; with an ammonia solution of silver oxide - substances from test tubes 1 and 4. Substances from test tubes 1, 4, 5 react with an aqueous solution of sodium hydroxide.
Determine the contents of the numbered tubes.
Solution. For recognition, let’s draw up Table 2 and immediately make a reservation that the conditions of this problem do not take into account the possibility of a number of interactions, for example, methyl formate with bromine water, phenol with a solution of diammine silver hydroxide. The - sign denotes the absence of interaction, and the + sign denotes the ongoing chemical reaction.
table 2
Interactions of analytes with proposed reagents
Example 4. Six numbered test tubes contain solutions: isopropyl alcohol, sodium bicarbonate, acetic acid, aniline hydrochloride, glycerin, protein. How to determine which test tube contains each substance?
Solution. .
When bromine water is added to solutions in numbered test tubes, a precipitate is formed in the test tube with aniline hydrochloride as a result of its interaction with bromine water. The identified solution of aniline hydrochloric acid is used on the remaining five solutions. Carbon dioxide is released in a test tube containing sodium bicarbonate solution. The established solution of sodium bicarbonate acts on the other four solutions. Carbon dioxide is released in a test tube containing acetic acid. The remaining three solutions are treated with a solution of copper (II) sulfate, which causes the appearance of a precipitate as a result of protein denaturation. To identify glycerol, copper (II) hydroxide is prepared from solutions of copper (II) sulfate and sodium hydroxide. Copper(II) hydroxide is added to one of the remaining two solutions. When copper(II) hydroxide dissolves to form a clear, bright blue solution of copper glycerate, glycerol is identified. The remaining solution is an isopropyl alcohol solution.
Example 5. Seven numbered test tubes contain solutions of the following organic compounds: aminoacetic acid, phenol, isopropyl alcohol, glycerin, trichloroacetic acid, aniline hydrochloride, glucose. Using only solutions of the following as reagents inorganic substances: 2% copper (II) sulfate solution, 5% iron (III) chloride solution, 10% sodium hydroxide solution and 5% sodium carbonate solution, identify the organic substances contained in each test tube.
Solution. We immediately warn you that here we offer a verbal explanation of the identification of substances .
When iron(III) chloride solution is added to solutions taken from the numbered test tubes, a red color is formed with aminoacetic acid and a violet color with phenol. When adding a solution of sodium carbonate to samples of solutions taken from the remaining five test tubes, carbon dioxide is released in the case of trichloroacetic acid and aniline hydrochloride; there is no reaction with other substances. Aniline hydrochloride can be distinguished from trichloroacetic acid by adding sodium hydroxide to them. In this case, an emulsion of aniline in water is formed in a test tube with aniline hydrochloride; no visible changes are observed in a test tube with trichloroacetic acid. The determination of isopropyl alcohol, glycerol and glucose is carried out as follows. In a separate test tube, by mixing 4 drops of a 2% solution of copper (II) sulfate and 3 ml of a 10% solution of sodium hydroxide, a blue precipitate of copper (II) hydroxide is obtained, which is divided into three parts.
A few drops of isopropyl alcohol, glycerin and glucose are added separately to each part. In a test tube with the addition of isopropyl alcohol, no changes are observed; in test tubes with the addition of glycerin and glucose, the precipitate dissolves with the formation of complex compounds of intense blue color. Distinguish between formed complex compounds You can heat the top of the solutions in test tubes on a burner or alcohol lamp until they begin to boil. In this case, no color change will be observed in the test tube with glycerol, and in the upper part of the glucose solution a yellow precipitate of copper (I) hydroxide appears, turning into a red precipitate of copper (I) oxide; the lower part of the liquid, which was not heated, remains blue.
Example 6. Six test tubes contain aqueous solutions of glycerin, glucose, formalin, phenol, acetic and formic acid. Using the reagents and equipment on the table, identify the substances in the test tubes. Describe the process of determination. Write the reaction equations on the basis of which the substances are determined.
Reagents: CuSO 4 5%, NaOH 5%, NaHCO 3 10%, bromine water.
Equipment: rack with test tubes, pipettes, water bath or hotplate.
Solution
1. Determination of acids.
When carboxylic acids interact with a solution of sodium bicarbonate, carbon dioxide is released:
HCOOH + NaHCO 3 → HCOONa + CO 2 + H 2 O;
CH 3 COOH + NaHCO 3 → CH 3 COONa + CO 2 + H 2 O.
Acids can be distinguished by reaction with bromine water. Formic acid discolors bromine water
HCOOH + Br 2 = 2HBr + CO 2.
Bromine does not react with acetic acid in an aqueous solution.
2. Determination of phenol.
When glycerin, glucose, formalin and phenol interact with bromine water, only in one case is the solution clouded and a white precipitate of 2,4,6-tribromophenol forms.
Glycerin, glucose and formalin are oxidized by bromine water, and discoloration of the solution is observed. Glycerol under these conditions can be oxidized to glyceraldehyde or 1,2-dihydroxyacetone
.
Further oxidation of glyceraldehyde leads to glyceric acid.
HCHO + 2Br 2 + H 2 O → CO 2 + 4HBr.
Reaction with freshly prepared copper(II) hydroxide precipitate allows one to distinguish between glycerol, glucose and formaldehyde.
When glycerin is added to copper(II) hydroxide, the blue cheesy precipitate dissolves and a bright blue solution of complex copper glycerate is formed. When heated, the color of the solution does not change.
Adding glucose to copper(II) hydroxide also produces a bright blue solution of the complex
.
However, when heated, the complex is destroyed and the aldehyde group is oxidized, resulting in a red precipitate of copper (I) oxide.
.
Formalin reacts with copper(II) hydroxide only when heated to form an orange precipitate of copper(I) oxide.
HCHO + 4Cu(OH) 2 → 2Cu 2 O↓ + CO 2 + 5H 2 O.
All described interactions can be presented in Table 3 for ease of determination.
Table 3
Determination results
Literature
1. Traven V. F. Organic chemistry: Textbook for universities: In 2 volumes / V. F. Traven. – M.: ICC “Akademkniga”, 2006.
2. Smolina T. A. et al. Practical work in organic chemistry: Small workshop. Textbook for universities. / T. A. Smolina, N. V. Vasilyeva, N. B. Kupletskaya. – M.: Education, 1986.
3. Kucherenko N. E. et al. Biochemistry: Workshop /N. E. Kucherenko, Yu. D. Babenyuk, A. N. Vasiliev and others - K.: High School, Kyiv Publishing House. Univ., 1988.
4. Shapiro D.K. Workshop on biological chemistry. – Mn: Higher School, 1976.
5. V. K. Nikolaenko. Solving problems of increased complexity in general and inorganic chemistry: A manual for teachers, Ed. G.V. Lisichkina - K.: Rad.shk., 1990.
6. S. S. Churanov. Chemistry Olympiads at school: A manual for teachers. – M.: Education, 1962.
7. Moscow city chemical Olympiads: Guidelines. Compiled by V.V. Sorokin, R.P. Surovtseva - M,: 1988
8. Modern chemistry in the problems of international olympiads. V. V. Sorokin, I. V. Svitanko, Yu. N. Sychev, S. S. Churanov - M.: Chemistry, 1993
9. E. A. Shishkin. Teaching students to solve quality problems in chemistry. – Kirov, 1990.
10. Chemistry Olympiads in problems and solutions. Parts 1 and 2. Compiled by Kebets A.P., Sviridov A.V., Galafeev V.A., Kebets P.A. - Kostroma: KGSHA Publishing House, 2000.
11. S. N. Perchatkin, A. A. Zaitsev, M. V. Dorofeev. Chemical Olympiads in Moscow. – M.: MIKPRO Publishing House, 2001.
12. Chemistry 10-11: Collection of problems with solutions and answers / V.V. Sorokin, I.V. Svitanko, Yu.N. Sychev, S.S. Churanov. – M.: “AST Publishing House”: LLC “Publishing House” ASTREL", 2001.
This task was proposed to 11th grade students at the practical round of the III (regional) stage All-Russian Olympiad schoolchildren in chemistry in the 2009-2010 academic year.
A. bromine water;
B. ammonia solution of silver oxide;
B. hydrogen bromide solution;
D. aqueous solution of KMnO 4
7. The sulfonation reaction most easily involves:
A. benzene;
B. toluene;
B. nitrobenzene;
G. benzoic acid;
D. benzenesulfonic acid.
8. The oxidation of toluene produces:
B. benzoic acid;
B. acetic acid;
G. benzene;
D. benzyl alcohol.
Liquid state of the first members of the homologous series of alcohols
due to:
A. non-polarity of molecules;
B. ability to hydrogenate;
B. ability to hydrate;
D. the presence of a hydrogen bond between its molecules.
10. When alcohols are heated in the presence of concentrated sulfuric acid, the following is formed:
A. carboxylic acid;
B. alcoholate;
B. aldehyde;
G. ester;
D. ether.
11. External effect of the reaction of glycerol with copper hydroxide II:
A. blue solution colors;
B. solution of blue colors;
B. blue sediment;
G. blue sediment;
D. green solution colors.
12. To detect phenolic hydroxyl, use the following reagent:
A. sulfuric acid solution;
B. solution of bromine water;
B. solution of ferric chloride III;
G. potassium permanganate solution;
D. sodium hydroxide solution.
13. When phenol reacts with bromine water, the following is formed:
A. metabromophenol;
B. picric acid;
B. carbolic acid;
G. 2,4,6-tribromophenol;
D. bromobenzene.
14. The –COOH group is called:
A. carbonyl group;
B. hydroxyl group;
B. carboxyl group;
G. oxo group
15. A reaction occurs between a carboxylic acid and an alcohol:
A. hydrolysis;
B. saponification;
B. isomerization;
G. esterification.
D. hydrogenation;
Homologues are
A. ethane and ethylene;
B. acetylene and ethylene;
B. benzene and toluene;
G. benzene and ethylene.
17. Alcohol is used in fat synthesis:
A. ethanol;
B. methanol;
B. glycerin;
G. isopropyl;
D. ethylene glycol.
The “silver mirror” reaction is possible with
A. benzene;
B. formic acid;
B. methyl alcohol;
G. dimethyl ether.
19. The composition of liquid fat reflects the name:
A. tristearate;
B. tripalmitate;
B. dipalmitostearate;
G. trioleate;
D. distearatopalmitate.
20. Amines exhibit __________ properties:
A. basic;
B. acidic;
B. acid-base.
21. External effect of the reaction of aniline with bromine water:
A. white precipitate;
B. yellow precipitate;
B. cherry red coloring;
G. brick-red sediment.
D. violet coloring;
Lignin paper is colored by the action of an aniline solution
in colour:
A. red;
V. yellow-orange;
G. blue;
D. black.
Are not isomers
A. butane and methylpropane;
B. pentane and 2-methylpentane;
B. butadiene-1,3 and butine-1;
G. ethanol and dimethyl ether.
By dehydration of ethanol we obtain
A. acetylene;
B. ethylene;
G. ethanal.
Substances that have the same molecular composition, but different
chemical structure is called...
A. isomers
B. homologues
B. radicals
26. Amyl (pentyl) has the formula:
A. C 4 H 9 –
V. C 5 H 11 –
G. S 7 N 15 –
27. This compound CH 3 - CH - CH - CH 2 - CH 3 has the name
CH 3 CH 3
according to international nomenclature:
A. 2-methyl-3-ethyl-methane
B. isopropyl-methyl-ethyl-methane
B. 2,2-dimethylpentane
G. 2,3-dimethylpentane
28. Alkanes under normal conditions:
A. do not oxidize
B. oxidize to alcohols
B. oxidize to aldehydes
G. oxidize to acids
29. Carbon atoms in alkenes are in the state:
A. sp hybridization
B. sp 2 - hybridization
B. sp 3 - hybridization
30. Find 3-methylhexene-2:
A. N 3 C - CH 2 - C = CH - CH 2 - CH 3
B. N 3 C - CH = CH - C = CH - CH 3
B. H 3 C - CH 2 - CH 2 - C = CH - CH 3
G. N 3 C – CH 2 - CH - CH 2 - CH 2 - CH 3
31. Qualitative reaction for unsaturated hydrocarbons:
A. with OH
B. with bromine water
32. Between the carbon atoms in the acetylene molecule there are the following bonds:
A. two s-bonds and one π-bond
B. three s-bonds
B. three π bonds
D. one s-bond and two π-bonds
33. The phenyl radical has the formula:
A. C 6 H 13 -
B. C 6 H 5 - CH 2 -
G. C 6 H 4 (CH 3) –
34. Substitution reactions in the benzene ring proceed according to the mechanism:
B. nucleophilic substitution
B. electrophilic substitution
35. To obtain benzene homologues, the following reaction is used:
A. alkylation
B. recovery
B. sulfonation
G. nitration
36. Iodoform has the formula:
37. Do not interact with alkalis:
A. phenols
B. esters
B. monocarboxylic acids
G. monohydric alcohols
38. During the oxidation of secondary alcohols, the following are formed:
A. ketones
B. carboxylic acids
B. aldehydes
G. hydroperoxides
39. Phenols are derivatives:
A. alkanov
B. alkenes
B. aromatic hydrocarbons
G. cyclohexane
40. Diatomic phenols include:
A. pyrogallol
B. phloroglucinol
G. resorcinol
41. The aldehyde group is identified by the formation reaction:
A. iodoform
B. silver mirror
B. azo dye
G. ester
42. Dibasic acids include:
A. formic acid
B. benzoic acid
V. salicylic acid
G. oxalica
43. Salts of oxalic acid are a reagent for the cation:
B. calcium
B. magnesium
44. Fats are:
A. esters of monohydric alcohols
B. glycerol ethers
B. esters of glycerol and higher carboxylic acids
G. esters of glycerol and mineral acids
45 The amino group (-NH 2) is an orienting agent of the 1st kind and directs
electrophilic reagents in position:
G. ortho- and para-
Qualitative reactions to proteins all except
A. xanthoproteinova
B. biuretova
B. salt precipitation heavy metals
D. formation of acrolein
47. Monosaccharides include:
A. starch
B. glucose
B. cellulose
G. glycogen
48. Qualitative reaction to starch:
A. with Tollens reagent
B. with Fehling's reagent
V. with iodine
G. with thymol
49. The following reacts with an ammonia solution of silver hydroxide:
A. glucose
B. glycogen
B. sucrose
G. starch
Barbiturates are used as
A. anti-inflammatory agent
B. antiseptic
B. antihistamine
G. sleeping pill
51. In the transformation scheme ethyn → x → acetic acid – substance x is:
A. CH 3 COH
B. CH 3 CH 3
B. CH 3 COOH
G. C 2 H 5 COH
52. An organic substance whose molecular formula is C 8 H 14 may belong to the homologous series:
A. methane
B. ethylene
B. benzene
G. acetylene
53. The groups - OH and - COOH are functional for:
A. alcohols and phenols
B. alcohols and carboxylic acids
B. aldehydes and ketones
G. phenols and aldehydes
54. Discoloration of bromine water will not occur when exposed to:
A. pentene – 2
B. pentadiene – 1, 3
B. cyclopentane
G. pentina – 2
55. The “silver mirror” does not react with:
A. ethanol
B. acetaldehyde
B. formic acid
G. propanal
56. The main product of the reaction of chloroethane with an alcohol solution of potassium hydroxide is:
A. ethylene
B. ethyl alcohol
G. potassium ethoxide
57. A substance whose molecule contains carbon atoms in the state of sp 3 - and sp - hybridization:
B. butene – 1
V. butine – 1
G. butadiene – 1, 3
58. Phenol can react with each of two substances:
A. NaOH and HNO 3
B. Cu(OH) 2 and HCl
B. K 2 CO 3 and CuO
D. NaOH and CH 4
59. Cyclohexane is a structural isomer:
A. hexane
B. hexene – 2
V. hexina – 2
G. benzene
60. When alkenes are hydrogenated, the following are formed:
A. alkanes
B. alkynes
B. alkadienes
G. alcohols
61. The product of the reaction of propene with chlorine is:
A. 1, 2 – dichloropropene
B. 2 – chlorpropene
B. 2 – chloropropane
G. 1, 2 – dichloropropane
62. Substances “X” and “Y” in the transformation scheme are:
C 2 H 5 Cl -→ C 2 H 5 OH -→ C 2 H 5 ONa
A. X – KOH; Y – NaCl
B. X – HOH; Y-NaOH
B. X – KOH; Y–Na
G. X – O 2; Y–Na
63. When acetaldehyde is hydrogenated, it forms:
A. acetylene
B. acetic acid
B. ethanol
G. ethylene glycol
64. A homologue of acetic acid is the acid:
A. chloroacetic
B. formic
B. oleic
G. benzoin
65. Formic acid can exhibit the following properties:
A. aldehyde and alcohol
B. carboxylic acid and alcohol
B. carboxylic acid and aldehyde
G. carboxylic acid and alkene
This connection
NS ≡ C – CH – CH – CH 3
