Lesson summary "Genetic relationship between the main classes of organic compounds. Solving problems "
74. Write the equations and name the reaction products according to the scheme:
75. Write the equations and name the reaction products according to the scheme:
76. Write the equations and name the reaction products according to the scheme:
77. Write the equations and name the reaction products according to the scheme:
78. Write the equations and name the reaction products according to the scheme:
79. Write the equations and name the reaction products according to the scheme:
80. Write the equations and name the reaction products according to the scheme:
81. Write the equations and name the reaction products according to the scheme:
82. Write the equations and name the reaction products according to the scheme:
83. Write the equations and name the reaction products according to the scheme:
84. Write the equations and name the reaction products according to the scheme:
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86. Write the equations and name the reaction products according to the scheme:
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90. Write the equations and name the reaction products according to the scheme:
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92. Write the equations and name the reaction products according to the scheme:
93. Write the equations and name the reaction products according to the scheme:
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100. Write the equations and name the reaction products according to the scheme:
101. Write the equations and name the reaction products according to the scheme:
Module 2. Heterocyclic and natural compounds
Five-membered heterocyclic compounds
1. Write the schemes and name the reaction products of aziridine with the following reagents: a) Н 2 О (t); b) NH 3 (t); c) HC1 (t).
2. Give the scheme of the reaction of extraction of oxirane. Write the equations and name the reaction products of oxirane: a) with H 2 O, H +; b) with C 2 H 5 OH, H +; c) with CH 3 NH 2.
3. Give the schemes of mutual transformations of five-membered heterocycles with one heteroatom (Yuriev's cycle of reactions).
4. What is acidophobia? What heterocyclic compounds are acidophobic? Write the reaction schemes for sulfonation of pyrrole, thiophene, indole. Name the products.
5. Give the schemes and name the products of the reactions of halogenation and nitration of pyrrole and thiophene.
6. Give the schemes and name the end products of the oxidation and reduction reactions of furans and pyrrole.
7. Give the scheme of the reaction for the extraction of indole from N-formyl o toluidine. Write down the reaction equations for the nitration and sulfonation of indole. Name the products.
8. Give the scheme of the reaction of extraction of 2-methylindole with phenylhydrazine by the Fisher method. Write the equations and name the reaction products of 2-methyl-indole: a) with KOH; b) with CH 3 I.
9. Give and name the tautomeric forms of indoxyl. Write a diagram of the reaction of the extraction of indigo blue from indoxyl.
10. Give the schemes and name the products of the reduction and oxidation reactions of indigo blue.
11. Write the schemes and name the reaction products for 2-aminothiazole: a) with HC1; a) with (CH 3 CO) 2 O; c) with CH 3 I.
12. What type of tautomerism is typical for azoles, what is the reason for it? Give the tautomeric forms of pyrazole and imidazole.
13. Give the scheme for the synthesis of imidazole from glyoxal. Confirm the amphoteric character of imidazole by the schemes of the corresponding reactions. Name the reaction products.
14. Give the reaction schemes confirming the amphoteric nature of pyrazole, benzimidazole, nicotinic (3-pyridinecarboxylic) acid, anthranilic (2-aminobenzoic) acid.
15. Write a scheme for the synthesis of 3-methylpyrazolone-5 from acetoacetic ether and hydrazine. Give and name the three tautomeric forms of pyrazolone-5.
16. Write a scheme for the synthesis of antipyrine from acetoacetic ether. Give a diagram and name the product of a qualitative reaction to antipyrine.
17. Write a scheme for the synthesis of amidopyrine from antipyrine. Indicate the qualitative reaction to amidopyrine.
Six-membered heterocyclic compounds
18. Write diagrams and name the reaction products confirming the basic properties of pyridine and the amphoteric properties of imidazole.
19. Draw and name the tautomeric forms of 2-hydroxypyridine. Write the equations and name the reaction products for 2-hydroxypyridine: a) with PCl 5; b) with CH 3 I.
20. Draw and name the tautomeric forms of 2-aminopyridine. Write the equation and name the reaction products of 2-aminopyridine and 3-aminopyridine with hydrochloric acid.
21. Give the schemes and name the reaction products confirming the presence of a primary aromatic amino group in b-aminopyridine.
22. Give a scheme for the synthesis of quinoline by the Scraup method. Name the intermediate connections.
23. Give the scheme for the synthesis of 7-methylquinoline by the Scraup method. Name all intermediate connections.
24. Give the scheme for the synthesis of 8-hydroxyquinoline by the Scraup method. Name the intermediate connections. Confirm the amphoteric character of the final product by chemical reactions.
25. Give the schemes and name the products of the reactions of sulfonation, nitration and oxidation of quinoline.
26. Write the schemes and name the reaction products of quinoline: a) with CH 3 I; b) with KOH; c) with room HNO 3, room H 2 SO 4; d) with HC1.
27. Give the schemes and name the products of the reactions of nitration of indole, pyridine and quinoline.
28. Give the schemes and name the reaction products of isoquinoline: a) with CH 3 I; b) with NaNH 2, NH 3; c) with Br 2, FeBr 3.
29. Give the scheme for the synthesis of acridine from N-phenylanthranilic acid by the Rubtsov-Magidson-Grigorovsky method.
30. Give the scheme of the reaction of extraction of 9-aminoacridine from acridine. Write the equations and name the products of the interaction of 9-aminoacridine a) with HCl; b) s (CH 3 CO) 2 O.
31. Give the schemes of oxidation and reduction reactions of quinoline, isoquinoline and acridine. What are the final products?
32. Write the equations and name the reaction products g-Piron with conc. hydrochloric acid. Give the formulas of natural compounds, the structure of which includes the cycles g-Piron and a-Piron.
33. Write the schemes and name the reaction products of pyridine: a) with НСІ; b) with NaNH 2, NH 3; c) with KOH.
34. Write the schemes and name the reaction products of 4-aminopyrimidine: a) with overlap. HCI; b) with NaNH 2, NH 3; c) with Br 2) FeBr 3.
35. Give the scheme for the synthesis of barbituric acid from malonic ester and urea. What is the reason for the acidic nature of barbituric acid? Confirm the answer with the schemes of the corresponding reactions.
36. Give the scheme of tautomeric transformations and name the tautomeric forms of barbituric acid. Write the equation for the reaction of barbituric acid with an aqueous alkali solution.
37. Give a reaction scheme for the extraction of 5.5-diethylbarbituric acid from malonic ester. Write the equations and name the product of the interaction of the named acid with alkali (aq. Solution).
38. Give the schemes, indicate the type of tautomerism and name the tautomeric forms of nucleic bases of the pyrimidine group.
39. Write the scheme of interaction of uric acid with alkali. Why is uric acid dibasic and not three basic ones?
40. Give the equations of the qualitative reaction for uric acid. What are the intermediate and final products?
41. Write a diagram of tautomeric equilibrium and name the tautomeric forms of xanthine. Give the equations and name the reaction products that confirm the amphoteric nature of xanthine.
42. Give the schemes, indicate the type of tautomerism and name the tautomeric forms of the nucleic acid bases of the purine group.
43. Which of the following compounds is characteristic of lactam-lactimna tautomerism: a) hypoxanthine; b) caffeine; c) uric acid? Give diagrams of the corresponding tautomeric transformations.
Natural compounds
44. Write the schemes and name the reaction products of menthol: a) with НСІ; b) with Na; c) with isovaleric (3-methylbutanoic) acid in the presence of K. H 2 SO. Name menthol by the IUPAC nomenclature.
45. Give the schemes of sequential reactions of obtaining camphor from a-pinene. Write the reaction equations confirming the presence of a carbonyl group in the structure of camphor. Name the products.
46. Give the diagrams and name the hydro-products of the interaction of camphor: a) with Br 2; b) with NH 2 OH; c) with Н 2, Ni.
47. Give the scheme of the reaction of extraction of camphor from bornyl acetate. Write the reaction equation confirming the presence of a carbonyl group in the structure of camphor.
48. What compounds are called epimers? Using the example of D-glucose, explain the phenomenon of epimerization. Give the projection formula for hexose, epimeric and D-glucose.
49. What phenomenon is called mutarotation? Give the scheme of cyclo-chain tautomeric transformations of b-D-glucopyranose to aqueous solution... Name all forms of monosaccharides.
50. Give the scheme of the cyclo-chain tautomeric transformation of D-galactose in an aqueous solution. Name all forms of monosaccharide.
51. Give the scheme of the cyclo-chain tautomeric transformation of D-mannose in aqueous solution. Name all forms of monosaccharide.
52. Give the scheme of the cyclo-chain tautomeric transformation of a-D-fructofuranose (water. Solution). Name all forms of monosaccharides.
53. Write the schemes of sequential reactions of the formation of fructose ozazone. Still monoses form the same ozazone?
54. Give the schemes of reactions proving the presence of glucose in the molecule: a) five hydroxyl groups; b) acetal hydroxyl; c) aldehyde group. What are the reaction products?
55. Write the reaction schemes for fructose with the following reagents: a) HCN; b) C 2 H 5 OH, H +; c) App. CH 3 I; r) Ag (NH 3) 2 OH. Name the compounds obtained.
56. Write the reaction schemes for the conversion of D-glucose: a) into methyl-b-D-glucopyranoside; b) pentaacetyl-b-D-glucopyranose.
57. Give the formula and give chemical name disaccharide, which, upon hydrolysis, will give glucose and galactose. Write the reaction schemes for its hydrolysis and oxidation.
58. What are reducing and non-reducing sugars? Of the disaccharides - maltose or sucrose, will react with Tollens' reagent (ammonia solution of argentum oxide)? Give the formulas of these disaccharides, give them names according to the IUPAC nomenclature, write the reaction scheme. What disaccharides can be used in a- and b-forms?
59. What carbohydrates are called disaccharides? What are reducing but not reducing sugars? React maltose, lactose and sucrose with Tollens reagent (ammonia solution of argentum oxide)? Give the reaction equations, give the names according to the IUPAC nomenclature for the indicated disaccharide.
60. Write the schemes of sequential reactions for obtaining ascorbic acid from D-glucose. Indicate the acid site in the vitamin C molecule.
61. Write the reaction schemes for obtaining: a) 4-O-a-D-glucopyranosido-D-glucopyranose; b) a-D-glucopyranoside-b-D-fructofuranoside. What are the original monosaccharides? What type of disaccharides each of c-c a) and b) belongs to?
62. Give the scheme of the reaction allowing to distinguish sucrose from maltose. Give names according to the IUPAC nomenclature of these disaccharides, show the schemes of their hydrolysis.
63. Give the scheme for the synthesis of methyl-b-D-galactopyranoside from D-galactose and its acid hydrolysis.
Similar information.
Molecular structure organic compounds allows to draw a conclusion about the chemical properties of substances and the close relationship between them. Compounds of other classes are obtained from substances of some classes by successive transformations. Moreover, all organic substances can be represented as derivatives of the most simple connections- hydrocarbons. The genetic relationship of organic compounds can be represented as a diagram:
С 2 Н 6 → С 2 Н 5 Br → С 2 Н 5 OH → СН 3 -СОН → СН 3 СООН →
CH 3 COOC 3 H 7; and etc.
According to the scheme, it is necessary to draw up equations for the chemical transformations of some substances into others. They confirm the interconnection of all organic compounds, the complication of the composition of matter, the development of the nature of substances from simple to complex.
Part organic matter most often includes a small number of chemical elements: hydrogen, carbon, oxygen, nitrogen, sulfur, chlorine and other halogens. The organic substance methane can be synthesized from two simple inorganic substances - carbon and hydrogen.
C + 2H 2 = CH 4 + Q
This is one example of the fact that between all substances of nature - inorganic and organic - there is a unity and genetic connection, which are manifested in the mutual transformations of substances.
Part 2. Execute practical task.
The task is experimental.
Prove that potatoes contain starch.
To prove the presence of starch in potatoes, a drop of iodine solution should be applied to the cut of the potato. The cut of the potato will turn blue-violet. The reaction with iodine solution is a qualitative reaction to starch.
E T A L O N
to option 25
Number of options(packages) of tasks for examiners:
Option number 25 from 25 options
Time for completing tasks:
Option number 25 45 min.
Conditions for completing tasks
Labor protection requirements: teacher (expert) supervising assignments(safety briefing when working with reagents)
Equipment: paper, ball pen, laboratory equipment
Literature for examiners reference, methodical and tables
1. Familiarize yourself with exam assignments, skills assessed, knowledge and assessment indicators. .
Option number 25 of 25
Part 1. Answer theoretical questions:
1. Aluminum. Amphotericity of aluminum. Aluminum oxides and hydroxides.
2. Proteins are natural polymers. The structure and structure of proteins. Qualitative reactions and applications.
Part 2. Complete the Practice Activity
3. The problem is experimental.
How empirically get oxygen in the laboratory, prove its presence.
Option 25 of 25.
There is a genetic relationship between the various classes of organic substances, which allows the synthesis of the desired compounds based on the chosen transformation scheme. In turn, the simplest organic substances can be obtained from inorganic substances. As an example, consider the practical implementation of reactions according to the following scheme:
CH3 CH2 OH | |||||||||||||||||
CH C O |
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acetic to - that aminoacetic to - that.
1) From carbon (graphite), methane can be obtained by direct synthesis:
C + 2H2 | CH4, |
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or in two stages - through aluminum carbide:
3C + 4Al t Al4 C3
Al4 C3 + 12H2 OCH4 + Al (OH) 3.
2) Ethylene can be obtained from methane different ways in several stages, for example, you can carry out the Wurtz synthesis followed by the dehydrogenation of ethane:
2CH3 Br + 2Na | CH3 + 2NaBr | |||||||||||||||
or thermal cracking of methane and partial hydrogenation of the resulting acetylene:
2CH4 | 1500 o C | CH + 3H2 |
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CHCH + H2 Ni CH2 CH2.
3) Ethyl alcohol is obtained by hydration of ethylene in the presence of an inorganic acid:
CH2 CH2 + H2 OH +, t CH3 CH2 OH.
4) Acetic aldehyde (ethanal) can be obtained by dehydrogenation of ethanol on a copper catalyst, or by oxidation of alcohol with copper (II) oxide:
200 o C | O + H | |||||||||
CH3 CH2 OH + CuO | CH3 C | Cu + H2 O |
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5) Acetic aldehyde is easily oxidized to acetic acid, for example, by the "silver mirror" reaction, or by interaction with an acidified solution of KMnO4 or K2 Cr2 O7 when heated. This can be schematically shown by the following equation (try to compose complete equations reactions):
CH C O | |||||
6) The synthesis of aminoacetic acid is carried out through the intermediate stage of obtaining chloroacetic acid:
CH3 CO OH + Cl2 P (red) ClCH2 CO OH + HCl
ClCH2 C | 2NH3 | CH2 C | NH4 Cl |
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Please note that halogenated organic compounds, due to their high reactivity, are often used in organic syntheses as starting and intermediate substances.
The material world in which we live and of which we are a tiny part is one and at the same time infinitely diverse. Unity and diversity chemical substances of this world is most clearly manifested in the genetic connection of substances, which is reflected in the so-called genetic series. Let's highlight the most characteristic signs such rows:
1. All substances of this series must be formed by one chemical element... For example, a series written using the following formulas:
2. Substances formed by the same element must belong to different classes, that is, reflect different shapes its existence.
3. Substances that form the genetic line of one element must be linked by interconversions. On this basis, complete and incomplete genetic series can be distinguished.
For example, the above genetic lineup of bromine will be incomplete, incomplete. And here is the next row:
can already be seen as complete: it begins simple substance bromine and ends with it.
Summarizing the above, we can give the following definition of the genetic series:
Genetic relationship is a more general concept than the genetic series, which is, albeit a bright, but private manifestation of this relationship, which is realized in any mutual transformations of substances. Then, obviously, the first series of substances given in the text of the paragraph also fits this definition.
To characterize the genetic relationship of inorganic substances, we will consider three types of genetic series: the genetic series of the metal element, the genetic series of the non-metal element, the genetic series of the metal element, which corresponds to the amphoteric oxide and hydroxide.
I. The genetic rad of the metal element. The richest in substances is a number of metals, which exhibit different oxidation states. As an example, consider the genetic series of iron with oxidation states +2 and +3:
Recall that to oxidize iron to iron (II) chloride, you need to take a weaker oxidizing agent than to obtain iron (III) chloride:
II. Genetic range of a non-metal element. Similar to the metal series, a number of non-metal with different oxidation states is richer in bonds, for example, the genetic series of sulfur with oxidation states +4 and +6:
Only the last transition can cause difficulty. If you perform tasks of this type, then be guided by the rule: in order to get a simple substance from an oxidized compound of an element, you need to take its most reduced compound for this purpose, for example, a volatile hydrogen compound non-metal. In our example:
According to this reaction, sulfur is formed from volcanic gases in nature.
Likewise for chlorine:
III. The genetic series of the metal element, to which the amphoteric oxide and hydroxide correspond, is very rich in bonds, since, depending on the conditions, they exhibit either the properties of an acid or the properties of a base. For example, consider the genetic makeup of aluminum:
V organic chemistry should also be distinguished more general concept- "genetic link" and a more particular concept - "genetic series". If the basis of the genetic series in inorganic chemistry is made up of substances formed by one chemical element, then the basis of the genetic series in organic chemistry (the chemistry of carbon compounds) is made up of substances with the same number of carbon atoms in the molecule. Consider the genetic series of organic substances, in which we include greatest number connection classes:
Each digit corresponds to a specific reaction equation:
The last transition does not fit the definition of the genetic series - a product is formed not with two, but with a multitude of carbon atoms, but with its help the genetic connections are most diversely represented. And finally, we will give examples of the genetic relationship between the classes of organic and inorganic compounds, which prove the unity of the world of substances, where there is no division into organic and inorganic substances... For example, consider the scheme for obtaining aniline - an organic substance from limestone - an inorganic compound:
Let's take the opportunity to repeat the names of the reactions corresponding to the proposed transitions:
Questions and tasks for § 23
Generalizing lesson
Lesson objectives:
Ensure the assimilation of students of knowledge about the genetic relationship between classes of organic compounds;
Development of the ability to think independently;
Create conditions for the development of skills for independent and collective work.
Lesson Objectives:
Continue the formation of the ability of students to apply previously acquired knowledge;
Development logical thinking;
Development of the speech culture of students;
Development of cognitive interest in the subject.
During the classes:
1. Introduction.
2. Warm up.
3. Quiz: "Guess the substance."
4. Drawing up the genetic chain.
5. Homework.
Introduction. Knowing the chemistry of functional groups, possible ways their replacement, the conditions for their transformation, it is possible to plan organic synthesis, moving from relatively simple compounds to more complex ones. In Carroll's famous book Alice in Wonderland, Alice addresses the Cheshire Cat: "Please tell me where to go?" To which the Cheshire Cat reasonably remarks: "It largely depends on where you want to go." How to connect this dialogue with the genetic link? We will try using knowledge on chemical properties organic compounds, to carry out transformations from the simplest representatives of alkanes to high-molecular compounds.
I. Warm up.
1. Review the classes of organic compounds.
2. What are the structure of the series of transformations?
3. Solving the series of transformations:
1) CaC2 → C2H2 → C6H6 → C6H5Cl → C6H5OH → C6H2Br3OH
2) Al4C4 → CH4 → C2H2 → C6H6 → C6H5ONa → C6H5OCH3
3) hexane → benzene → chlorobenzene → toluene → 2.4.6-tribromotoluene
II. Quiz: "Guess the substance."
Assignment to students: determine the substance about which in question and say a few words about this substance. (The student at the blackboard writes down the formulas of substances).
1) This substance is called bog gas, is the basis natural gas, a valuable and affordable raw material for the synthesis of many substances. (Methane)
Teacher Supplement: One curious post about where methane came in handy. Specialists from one of the research laboratories of the US Navy managed to develop a method for producing artificial diamonds. Methane was fed to a tungsten plate heated to 2500 C, on which the crystals formed in this case were deposited.
2) This substance is called luminous gas. This gas was initially used mainly for lighting: Street lights, theatrical ramps, hiking and mining lanterns. Older bicycles were fitted with carbide lights. Water entered a vessel filled with calcium carbide, and the resulting gas through a special nozzle entered the lamp, where it burned with a bright flame. (Acetylene)
3) The structure of this substance was established for 40 years, and the solution came when a snake appeared in Kekule's imagination, biting its own tail. (Benzene)
4) By special experiments, it was found that when the content of this substance in the air is about 0.1%, vegetables and fruits ripen faster. This substance is called a plant growth regulator. (Ethylene)
Addition of the teacher: it turns out that ethylene is needed for flowering pineapples. On plantations, fuel oil is burned, and small amounts of ethylene produced are enough to obtain a crop. And at home, you can use a ripe banana, which also releases ethylene. By the way, ethylene can transmit information. In Kudu antelopes, the main food is acacia leaves, which produce tannin. This substance gives the leaves a bitter taste, and in high concentrations it is poisonous. Antelopes are good at picking leaves with a low tannin content, but extreme conditions eat any and perish. It turns out that the leaves eaten by the antelopes secrete ethylene, which serves as a signal for neighboring acacias, and after half an hour their leaves produce tannin vigorously, which leads to the death of the antelope.
5) Grape sugar. (Glucose.)
6) Wine alcohol. (Ethanol)
7) Oily liquid. Which was obtained from tolu balsam. (Toluene)
8) In case of danger, ants secrete this very substance. (Formic acid)
9) Explosive substance, which has several names: tol, TNT. TNT. Usually from 1 g of explosive, about 1 liter of gases is formed, which corresponds to a thousandfold increase in volume. The mechanism of action of any explosive is reduced to the instantaneous formation of a large volume of gas from a small volume of liquid or solid. The pressure of the expanding gases is the destructive force of the explosion. (Trinitrotoluene)
III. Genetic chain compilation.
Group work. The class is divided into groups of 4 people.
Task for the groups: compose a series of transformations, using as many substances as possible, guessed in the quiz. The task is offered for a while. After completion, the task is checked at the board.
At the end of the lesson, evaluate the students' answers.
Consider the genetic series of organic substances, in which we include the largest number of classes of compounds:
Each number above the arrow corresponds to a specific reaction urn (the reaction equation is indicated by a number with a prime):
IV. Homework: Make up a genetic series of transformations, including at least five classes of organic compounds.
