Summary of the lesson “Genetic link between the main classes of organic compounds. Problem Solving ”
74. Write the equations and name the reaction products according to the scheme:
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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 a reaction scheme for the production of oxirane. Write the equations and name the products of the reactions of oxirane: a) with H 2 O, H +; b) with C 2 H 5 OH, H +; c) with CH 3 NH 2.
3. Give schemes of mutual transformations of five-membered heterocycles with one heteroatom (Yuryev’s reaction cycle).
4. What is acidophobia? What heterocyclic compounds are acidophobic? Write the reaction schemes for sulfonation of pyrrole, thiophene, indole. What are the products?
5. Give the schemes and name the products of the halogenation and nitration reactions of pyrrole and thiophene.
6. Give the schemes and name the final products of the oxidation and reduction reactions of furans and pyrrole.
7. Give a reaction scheme for the production of indole from N-formyl o toluidine. Write the equations for the nitration and sulfonation of indole. What are the products?
8. Give the reaction scheme for the production of 2-methylindole with phenylhydrazine according to 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 reaction scheme for the production of indigo blue with indoxyl.
10. Give the schemes and name the products of the reactions of reduction and oxidation of indigo blue.
11. Write the schemes and name the reaction products of 2-aminothiazole: a) with HC1; a) c (CH 3 CO) 2 O; c) with CH 3 I.
12. What type of tautomerism is characteristic for azoles, what is its condition? Give tautomeric forms of pyrazole and imidazole.
13. Give the scheme for the synthesis of imidazole from glyoxal. Confirm the amphoteric nature of imidazole with the corresponding reaction schemes. What are the reaction products?
14. Give reaction schemes confirming the amphoteric nature of pyrazole, benzimidazole, nicotinic (3-pyridinecarboxylic) acid, anthranilic (2-aminobenzoic) acid.
15. Write a synthesis scheme for 3-methylpyrazolone-5 from acetoacetic ester and hydrazine. Give and name three tautomeric forms of pyrazolone-5.
16. Write a scheme for the synthesis of antipyrine with acetoacetic ester. Give the scheme and name the product of a qualitative reaction to antipyrine.
17. Write a scheme for the synthesis of amidopyrine with antipyrine. Indicate the qualitative response to amidopyrine.
Six membered heterocyclic compounds
18. Write the schemes and name the reaction products that confirm the basic properties of pyridine and amphoteric properties of imidazole.
19. Represent and name tautomeric forms 2-hydroxypyridine. Write the equations and name the reaction products 2-hydroxypyridine: a) with PCl 5; b) with CH 3 I.
20. Depict 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 the synthesis scheme of quinoline according to the Scrap method. What are the intermediate compounds?
23. Give the synthesis scheme for 7-methylquinoline by the Scrap method. Name all intermediates.
24. Give the synthesis scheme for 8-hydroxyquinoline by the Scrap method. What are the intermediate compounds? By chemical reactions confirm the amphoteric nature of the final product.
25. Give 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 K. HNO 3, K. H 2 SO 4; d) with HC1.
27. Give the schemes and name the reaction products 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 a scheme for the synthesis of acridine from N-phenylanthranilic acid according to the Rubtsov-Magidson-Grigorovsky method.
30. Give a reaction scheme for the production of 9-aminoacridine with acridine. Write the equations and name the products of the interaction of 9-aminoacridine a) with HCI; b) s (CH 3 CO) 2 O.
31. Give the reaction schemes for the oxidation and reduction 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 4-aminopyrimidine: a) with sup. НСІ; b) with NaNH 2, NH 3; c) with Br 2) FeBr 3.
35. Give a scheme for the synthesis of barbituric acid from malonic ester and urea. What determines the acid character of barbituric acid? Confirm the answer with schemes of corresponding reactions.
36. Give the scheme of tautomeric transformations and name the tautomeric forms of barbituric acid. Write the equation of reaction of barbituric acid with an aqueous solution of alkali.
37. Give a reaction scheme for the production 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. R-p).
38. Give the schemes, indicate the type of tautomerism, and name the tautomeric forms of the nucleic bases of the pyrimidine group.
39. Write a diagram of the interaction of uric acid with alkali. Why is uric acid dibasic rather than three main?
40. Give the equations of a qualitative reaction to uric acid. What are the intermediate and final products.
41. Write a scheme of tautomeric equilibrium and name the tautomeric forms of xanthine. Give the equations and name the reaction products confirming the amphoteric nature of xanthine.
42. Give the schemes, indicate the type of tautomerism, and name the tautomeric forms of the nucleic 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 the schemes of the corresponding tautomeric transformations.
Naturally connected
44. Write the schemes and name the reaction products of menthol: a) with НСІ; b) with Na; c) with isovalerianic (3-methylbutanoic) acid in the presence of K. H 2 SO. Name the menthol according to the IUPAC nomenclature.
45. Give schemes of sequential reactions of camphor production with a-pinene. Write the reaction equations confirming the presence of a carbonyl group in the camphor structure. What are the products?
46. \u200b\u200bGive the schemes and name the gyro products of camphor interaction: a) with Vg 2; b) with NH 2 OH; c) with H 2, Ni.
47. Give a reaction scheme for the production of camphor with bornyl acetate. Write a reaction equation confirming the presence of a carbonyl group in the camphor structure.
48. What compounds are called epimers? Using the example of D-glucose, explain the phenomenon of epimerization. Give the projection formula of hexose, epimerno D-glucose.
49. What phenomenon is called mutarotation? Give the scheme of cyclic-chain tautomeric transformations of b-D-glucopyranose in aqueous solution. Name all forms of monosaccharides.
50. Give a diagram of the cyclic chain tautomeric conversion of D-galactose in an aqueous solution. Name all forms of monosaccharide.
51. Give a diagram of the cyclic chain tautomeric conversion of D-mannose in an aqueous solution. Name all forms of monosaccharide.
52. Give the scheme of cyclic-chain tautomeric transformation of a-D-fructofuranose (water. Solution). Name all forms of monosaccharides.
53. Write a sequence of successive reactions of formation of fructose ozone. Still monoses form the same ozone?
54. Give reaction schemes proving the presence of glucose in the molecule: a) five hydroxyl groups; b) napivacetal hydroxyl; c) aldehyde group. What are the reaction products?
55. Write the reaction schemes of fructose with the following reagents: a) HCN; b) C 2 H 5 OH, H +; c) CH 3 I; r) Ag (NH 3) 2 OH. What are the compounds obtained.
56. Write the reaction schemes for the conversion of D-glucose: a) to methyl-b-D-glucopyranoside; b) in pentaacetyl-b-D-glucopyranose.
57. Give the formula and give the chemical name of the disaccharide, which upon hydrolysis will produce glucose and galactose. Write the reaction schemes of its hydrolysis and oxidation.
58. What are reducing and non-reducing sugars? Of the disaccharides, maltose or sucrose, will react with the Tollens reagent (ammonium oxide argentum oxide)? Give the formulas of these disaccharides, give them names according to the IUPAC nomenclature, write the reaction scheme. What disaccharides can be removed in a- and b-forms?
59. What carbohydrates are called disaccharides? What are reducing but not reducing sugars? Maltose, lactose and sucrose react with Tollens reagent (ammonium oxide argentum oxide)? Give the reaction equations, give the names according to the IUPAC nomenclature with the indicated disaccharide.
60. Write a sequence diagram of the reactions for the production of ascorbic acid from D-glucose. Indicate the acid center 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 starting monosaccharides? To what type of disaccharides does each of c-a) and b) belong?
62. Give a reaction scheme that distinguishes sucrose from maltose. Give the names according to the IUPAC nomenclature to these disaccharides, suggest schemes for their hydrolysis.
63. Describe the synthesis of methyl-b-D-galactopyranoside from D-galactose and its acid hydrolysis.
Similar information.
The structure of the molecules of organic compounds allows us to conclude about the chemical properties of substances and the close relationship between them. Compounds of other classes are obtained from substances of one class by successive transformations. Moreover, all organic substances can be represented as derivatives of the simplest compounds - hydrocarbons. The genetic relationship of organic compounds can be represented in the form of a scheme:
C 2 H 6 → C 2 H 5 Br → C 2 H 5 OH → CH 3 -CHOH → CH 3 COOH →
CH 3 SOOC 3 H 7; and etc.
According to the scheme, it is necessary to draw up the equations of chemical transformations of some substances into others. They confirm the interconnection of all organic compounds, the complexity of the composition of the substance, the development of the nature of substances from simple to complex.
The composition of organic substances most often includes a small number of chemical elements: hydrogen, carbon, oxygen, nitrogen, sulfur, chlorine and other halogens. Organic matter methane can be synthesized from two simple inorganic substances - carbon and hydrogen.
C + 2H 2 \u003d CH 4 + Q
This is one example of the fact that between all the substances of nature - inorganic and organic - there is unity and a genetic connection that manifests itself in the mutual transformations of substances.
Part 2. Complete the practical task.
The task is experimental.
Prove that potatoes contain starch.
To prove the presence of starch in potatoes, a drop of iodine solution must be applied to the cut of the potato. A slice of potato will acquire a blue-violet color. 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 students:
Option number 25 of 25 options
Assignment time:
Option number 25 45 min
Terms of completing tasks
Labor protection requirements: teacher (expert) supervising assignments(reagent safety instructions)
Equipment: paper, ballpoint pen, laboratory equipment
Literature for students reference, methodical and tables
1. Become familiar with assignments for students being assessed by skills, knowledge, and assessment indicators. .
Option number 25 out of 25
Part 1. Answer the theoretical questions:
1. Aluminum. Amphotericity of aluminum. Oxides and hydroxides of aluminum.
2. Proteins are natural polymers. The structure and structure of proteins. Qualitative reactions and application.
Part 2. Complete the practical task
3. The task is experimental.
How to experimentally obtain oxygen in a laboratory, prove its availability.
Option 25 of 25.
There is a genetic relationship between different classes of organic substances, which allows synthesizing the necessary 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 the reactions according to the following scheme:
CH3 CH2 OH | |||||||||||||||||
CH C O |
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acetic acid. Aminoacetic acid.
1) Methane can be obtained from carbon (graphite) 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 from methane can be obtained in different ways in several stages, for example, it is possible to carry out Wurz synthesis followed by ethane dehydrogenation:
2CH3 Br + 2Na | CH3 + 2NaBr | |||||||||||||||
or carry out thermal cracking of methane and partial hydrogenation of the obtained 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 oxide (II):
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 reaction of a “silver mirror”, or by interaction with an acidified solution of KMnO4 or K2 Cr2 O7 when heated. Schematically, this can be shown by the following equation (try to compose complete reaction equations):
CH C O | |||||
6) The synthesis of aminoacetic acid is carried out through an 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 whose tiny particle we are is one and at the same time infinitely diverse. The unity and variety of chemicals in this world is most clearly manifested in the genetic connection of substances, which is reflected in the so-called genetic series. We single out the most characteristic features of such series:
1. All substances of this series should be formed by one chemical element. For example, a series written using the following formulas:
2. Substances formed by the same element should belong to different classes, that is, reflect different forms of its existence.
3. Substances that make up the genetic row of one element must be interconnected. On this basis, it is possible to distinguish between complete and incomplete genetic series.
For example, the above genetic series of bromine will be incomplete, incomplete. And here is the next row:
it can already be regarded as complete: it begins with simple bromine and ends with it.
Summarizing the above, the following definition of the genetic series can be given:
A genetic connection is a more general concept than a genetic series, which is even a striking, but particular manifestation of this connection, which is realized during 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 consider three varieties 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 correspond to amphoteric oxide and hydroxide.
I. The genetic rad of the metal element. The most rich in substances is a series of metal, in which various degrees of oxidation are manifested. As an example, consider the genetic series of iron with oxidation states of +2 and +3:
Recall that for the oxidation of iron to iron (II) chloride, you need to take a weaker oxidizing agent than to obtain iron (III) chloride:
II. Genetic row of non-metal element. Similarly to a series of metal, a series of non-metal with different oxidation states is richer in bonds, for example, the genetic series of sulfur with oxidation states +4 and +6:
Difficulty can cause only the last transition. If you perform tasks of this type, then follow the rule: to get a simple substance from the oxidized compound of an element, you need to take the most reduced compound for this purpose, for example, the volatile hydrogen compound of non-metal. In our example:
By this reaction, sulfur is formed from volcanic gases in nature.
Similarly for chlorine:
III. The genetic row of the metal element, to which amphoteric oxide and hydroxide correspond, is very rich in bonds, since they exhibit either acid properties or base properties depending on the conditions. For example, consider the genetic series of aluminum:
In organic chemistry, one should also distinguish between a more general concept - the "genetic link" and a more particular concept - the "genetic series". If the basis of the genetic series in inorganic chemistry is composed of substances formed by one chemical element, then the basis of the genetic series in organic chemistry (chemistry of carbon compounds) is composed of substances with the same number of carbon atoms in the molecule. Consider the genetic series of organic substances, which includes the largest number of classes of compounds:
Each digit corresponds to a specific reaction equation:
The last transition does not fit the definition of the genetic series - the product is formed not with two, but with many carbon atoms, but with its help the most diverse genetic relationships are represented. Finally, we 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 producing aniline, an organic substance from limestone, an inorganic compound:
We take the opportunity to repeat the names of the reactions corresponding to the proposed transitions:
Questions and assignments to § 23
Summary lesson
Lesson Objectives:
Ensure students learn about the genetic link between classes of organic compounds;
Development of independent thinking skills;
To create conditions for the development of independent and teamwork skills.
Lesson Objectives:
Continue to develop the ability of students to apply previously acquired knowledge;
Development of logical thinking;
The development of speech culture of students;
The development of cognitive interest in the subject.
During the classes:
1. Introduction.
2. Warm up.
3. Quiz: "Guess the substance."
4. Compilation of the genetic chain.
5. Homework.
Introduction Knowing the chemistry of functional groups, possible ways to replace them, the conditions for their transformations, it is possible to plan organic synthesis, moving from compounds that are relatively simple to more complex. 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 depends a lot on where you want to go.” How to connect this dialogue with a genetic link? We will try, using knowledge of the chemical properties of organic compounds, to carry out transformations from the simplest representatives of alkanes to high molecular weight compounds.
I. Warm up.
1. Repeat classes of organic compounds.
2. What are the structure of the series of transformations?
3. The solution of 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-tribromtoluene
II. Quiz: "Guess the Substance."
The task for the students: to identify the substance in question and say a few words about this substance. (The student writes the formulas of substances at the blackboard).
1) This substance is called - swamp gas, is the basis of 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 onto a tungsten plate heated to 2500 ° С, on which the crystals formed in this process settled.
2) This substance is called light gas. At first, this gas was used mainly for lighting: street lamps, theater ramps, camping and mining lights. On old bicycles carbide lights were installed. Water flowed into a vessel filled with calcium carbide, and the resulting gas through a special nozzle fell into a lamp, where it burned with a bright flame. (Acetylene)
3) The structure of this substance was established for 40 years, and the decision came when a snake appeared in Kekule’s imagination, biting its tail. (Benzene)
4) By special experiments, it was found that with the content of this substance in the air about 0.1%, vegetables and fruits ripen faster. This substance is called a plant growth regulator. (Ethylene)
Teacher's supplement: it turns out that ethylene is needed for flowering pineapples. Fuel oil is burned on the plantations, and small amounts of ethylene are sufficient to produce the crop. And at home, you can use a ripe banana, which also gives off 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 - poisonous. Antelopes can choose leaves with a low tannin content, but in extreme conditions they eat any and die. It turns out that the leaves eaten by antelopes secrete ethylene, which serves as a signal for neighboring acacias, and after half an hour their leaves intensely produce tannin, which leads to the death of antelopes.
5) Grape sugar. (Glucose.)
6) Wine alcohol. (Ethanol)
7) Oily liquid. Which was obtained from toluan balsam. (Toluene)
8) In danger, ants secrete this particular substance. (Formic acid)
9) An explosive that has several names: tol, trotyl. TNT. Usually about 1 liter of gases is formed from 1 g of explosive, which corresponds to a thousandfold increase in volume. The mechanism of action of any explosive is reduced to the instant 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. Generation of the genetic chain.
Work in groups. The class is divided into groups of 4 people.
Assignment to groups: make a series of transformations using as many substances as possible guessed in the quiz. The task is offered on time. After completing, the task is checked at the board.
At the end of the lesson, evaluate student responses.
Consider the genetic series of organic substances, which includes the largest number of classes of compounds:
Each digit above the arrow corresponds to a specific reaction urn (the reverse reaction equation is indicated by a number with a prime):
IV. Homework: Compile a genetic series of transformations, including at least five classes of organic compounds.
