Genetic series in organic chemistry. Presentation on the topic "genetic connection"

OPTION 1




2. Calculate the amount of the substance (in moles) and the mass of the substance (in grams) of each product during the subsequent transformations: ethane → bromoethane → ethanol, if ethane was taken with a mass of 90 g. The product yield at each stage of the synthesis was conditionally taken as 100%.



3. Make a diagram and equations of reactions by which carboxylic acids can be obtained from methane.


OPTION 2

1. Write the reaction equations with which you can carry out the following transformations:


2. Calculate the amount of the substance (in moles) and the mass of the substance (in grams) of each product during the following transformations: benzene → chlorobenzene → phenol, if benzene was taken with a mass of 156 g. The product yield at each stage of the synthesis was conditionally taken as 100%.


3. Draw a diagram and equations of reactions by which an amino acid can be obtained from ethylene.


OPTION 3

1. Write the reaction equations with which you can carry out the following transformations:



2. Calculate the amount of the substance (in moles) and the mass of the substance (in grams) of each product during the following transformations: benzene → nitrobenzene → aniline, if benzene was taken with a mass of 39 g. The product yield at each stage of the synthesis was conditionally taken as 100%.


3. Make a diagram and equations of reactions, with the help of which an ester can be obtained from coal.


OPTION 4

1. Write the reaction equations with which you can carry out the following transformations:




2. Calculate the amount of the substance (in moles) and the mass of the substance (in grams) of each product during the following transformations: chloromethane → methanol → methyl acetate, if chloromethane was taken with a mass of 101 g. The product yield at each stage of the synthesis was conditionally taken as 100%.


3. Make a diagram and equations of reactions by which an aromatic amine can be obtained from methane.

74. Write equations and name the reaction products according to the scheme:

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101. Write 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) H 2 O (t); b) NH 3 (t); c) HC1 (t).

2. Give the reaction scheme for the 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 schemes of mutual transformations of five-membered heterocycles with one heteroatom (Yur'ev reaction cycle).

4. What is acidophobia? What heterocyclic compounds are acidophobic? Write reaction schemes for sulfonation of pyrrole, thiophene, and indole. Name the products.

5. Give schemes and name the products of the reactions of halogenation and nitration of pyrrole and thiophene.

6. Give schemes and name the end products of the oxidation and reduction reactions of furans and pyrrole.

7. Give the reaction scheme for the extraction of indole from N-formyl o toluidine. Write the equations for the reactions of nitration and sulfonation of indole. Name the products.

8. Give the reaction scheme for the extraction of 2-methylindole from phenylhydrazine by the Fischer method. Write 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 scheme for the extraction of indigo blue from indoxyl.

10. Give schemes and name the products of the reduction and oxidation reactions of indigo blue.

11. Write the schemes and name the reaction products of 2-aminothiazole: a) with HC1; a) with (CH 3 CO) 2 O; c) with CH 3 I.

12. What type of tautomerism is characteristic of azoles, what is it due to? Give the tautomeric forms of pyrazole and imidazole.

13. Give a scheme for the synthesis of imidazole from glyoxal. Confirm the amphoteric nature of imidazole with the corresponding reaction schemes. Name the products of reactions.

14. Give schemes of reactions 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 ester and hydrazine. Give and name three tautomeric forms of pyrazolone-5.

16. Write a scheme for the synthesis of antipyrine from acetoacetic ester. Give a diagram and name the product of a qualitative reaction to antipyrine.

17. Write a scheme for the synthesis of amidopyrine from antipyrine. Specify a qualitative reaction to amidopyrine.

Six-membered heterocyclic compounds

18. Write the schemes 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 equations and name the reaction products of 2-hydroxypyridine: a) with PCl 5 ; b) with CH 3 I.

20. Draw and name the tautomeric forms of 2-aminopyridine. Write an equation and name the reaction products of 2-aminopyridine and 3-aminopyridine with hydrochloric acid.

21. Give 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 according to the Skraup method. Name the intermediate connections.

23. Give the scheme for the synthesis of 7-methylquinoline by the Skraup method. Name all intermediate connections.

24. Give the scheme for the synthesis of 8-hydroxyquinoline by the Skraup method. Name the intermediate connections. 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 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 schemes and name the products of the reactions of nitration of indole, pyridine and quinoline.

28. Give 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 according to the Rubtsov-Magidson-Grigorovsky method.

30. Give the reaction scheme for the extraction of 9-aminoacridine from acridine. Write equations and name the products of interaction of 9-aminoacridine a) with HCI; b) s (CH 3 CO) 2 O.

31. Give the schemes of reactions of oxidation and reduction of quinoline, isoquinoline and acridine. Name the end products.

32. Write equations and name the reaction products of g- Pyron with conc. hydrochloric acid. Give the formulas of natural compounds, the structure of which includes the cycles g-Pyron and a-Pyron.

33. Write the schemes and name the reaction products of pyridine: a) with HCI; b) with NaNH 2, NH 3; c) with CON.

34. Write the schemes and name the reaction products of 4-aminopyrimidine: a) with proper. NSI; 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 causes the acidic nature of barbituric acid? Support your answer with diagrams of the corresponding reactions.

36. Give a scheme of tautomeric transformations and name the tautomeric forms of barbituric acid. Write the equation for the reaction of barbituric acid with an aqueous solution of alkali.

37. Give the reaction scheme for the extraction of 5,5-diethylbarbituric acid from malonic ester. Write equations and name the product of the interaction of the named acid with an alkali (aqueous solution).

38. Give schemes, indicate the type of tautomerism and give the names of tautomeric forms of nucleic bases of the pyrimidine group.

39. Write a diagram of the interaction of uric acid with alkali. Why is uric acid dibasic and not tribasic?

40. Give the equations of a qualitative reaction to uric acid. List the intermediate and final products.

41. Write a diagram of tautomeric equilibrium and name the tautomeric forms of xanthine. Give equations and name the reaction products that confirm the amphoteric nature of xanthine.

42. Give schemes, indicate the type of tautomerism and give names to tautomeric forms of nucleic bases of the purine group.

43. Which of the following compounds is characterized by lactam-lactim tautomerism: a) hypoxanthine; b) caffeine; c) uric acid? Give schemes of corresponding tautomeric transformations.

Natural connections

44. Write the diagrams and name the reaction products of menthol: a) with HCI; b) with Na; c) with isovaleric (3-methylbutanoic) acid in the presence of k. H 2 SO. Name menthol according to the IUPAC nomenclature.

45. Give schemes of sequential reactions for 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 diagrams and name the gyroproducts of camphor interaction: a) with Br 2 ; b) with NH 2 OH; c) with H 2 , Ni.

47. Give the reaction scheme for the extraction of camphor from bornyl acetate. Write a reaction equation confirming the presence of a carbonyl group in the structure of camphor.

48. What compounds are called epimers? Using D-glucose as an example, explain the phenomenon of epimerization. Give the projection formula of hexose, epimeric D-glucose.

49. What phenomenon is called mutarotation? Give the scheme of cyclo-chain tautomeric transformations of b-D-glucopyranose in aqueous solution. Name all forms of monosaccharides.

50. Give the scheme of cyclo-chain tautomeric transformation of D-galactose in aqueous solution. Name all forms of monosaccharide.

51. Give the scheme of cyclo-chain tautomeric transformation of D-mannose in aqueous solution. Name all forms of monosaccharides.

52. Give the scheme of cyclo-chain tautomeric transformation of a-D-fructofuranose (water. solution). Name all forms of monosaccharides.

53. Write the schemes of successive reactions for the formation of fructose ozone. Do other monoses form the same ozone?

54. Give the reaction schemes proving the presence in the glucose molecule: a) five hydroxyl groups; b) napiacetal hydroxyl; c) aldehyde group. Name the reaction products.

55. Write the reaction schemes of fructose with the following reagents: a) HCN; b) C 2 H 5 OH, H +; c) over CH 3 I; r) Ag (NH 3) 2 OH. Name the resulting compounds.

56. Write the reaction schemes for the conversion of D-glucose: a) to methyl-b-D-glucopyranoside; b) into pentaacetyl-b-D-glucopyranose.

57. Give the formula and give the chemical name of the 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 it 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 non-reducing sugars? Do maltose, lactose and sucrose react 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-glucopyranoside-D-glucopyranose; b) a-D-glucopyranoside-b-D-fructofuranoside. Name the parent monosaccharides. What type of disaccharides does each of a) and b) belong to?

62. Give a reaction scheme that allows you to distinguish sucrose from maltose. Name these disaccharides according to the IUPAC nomenclature, direct the schemes of their hydrolysis.

63. Give a scheme for the synthesis of methyl-b-D-galactopyranoside from D-galactose and its acid hydrolysis.


Similar information.


In the school course of organic chemistry, the study of the genetic relationship between substances plays a significant role. Indeed, the course is based on the idea of ​​the development of substances as steps in the organization of matter. This idea is also implemented in the content of the course, where the material is arranged in order of complexity from the simplest hydrocarbons to proteins.

The transition from one class of organic substances to another is closely connected with the fundamental concepts of chemistry - a chemical element, a chemical reaction, homology, isomerism, a variety of substances and their classification. For example, in the genetic chain of transformations of methane - acetylene - acetic aldehyde, similar - the preservation of the element carbon in all substances - and different - forms of the existence of this element can be traced. Chemical reactions specify the theoretical provisions of the course, and many of them are important in practical terms. Therefore, often genetic transitions between substances are considered not only with the help of reaction equations, but are carried out and, practically, that is, the theory is connected with practice. Therefore, knowledge about the genetic relationship between substances is also necessary for the polytechnic education of students. When studying the genetic relationship between substances, the unity of nature, the interconnection of its phenomena, is revealed to students. So, inorganic compounds can also be included in the process of transformation of organic substances. This example reflects the intra-subject connection of the chemistry course. In addition, the chain of these transitions is part of a more general one - the phenomenon of the circulation of substances in nature. Therefore, each reaction studied in the course of chemistry acts as a separate link in the entire chain of transformations. At the same time, it turns out not only the method of obtaining the product, but also the conditions for the reaction (using information from physics and mathematics), the location of raw materials and factories (connection with geography), etc. There is also a problem - to foresee the further fate of the obtained substances and their decay products and their impact on the human environment. Thus, a number of information from other school subjects is applied and generalized in the material on genetic transitions.

The role of knowledge about the genetic connection between substances is also great in the formation of the dialectical-materialistic worldview of students. Revealing how the simplest hydrocarbons and other organic compounds were formed from inorganic substances, how the complication of their composition and structure led to the formation of proteins that initiated life, we thereby reinforce the materialistic theory of the origin of life on Earth with examples. The laws of dialectics, which students learn in the lessons of social science, are used in the study of genetic transitions. So, the question of the genetic relationship between substances with an integrated approach to it does not appear as a separate one, but is an integral part of the general in the education and upbringing of students.

An analysis of students' answers in lessons and exams shows that the question of the genetic relationship between substances causes difficulties. This is explained by the fact that the study of the question of genetic connection, although carried out throughout the course of chemistry, is carried out fragmentarily, unsystematically, without isolating the main direction.

In the diagram, the generalized formula corresponds to several groups of substances of the same composition, but of different structures. For example, the formula SpNgp+gO combines isomeric limit monohydric alcohols and ethers, respectively, having their own general formulas.

The straight lines in the general diagram show the main relationships between groups and classes of organic compounds. So, with the help of general formulas, transitions between groups of hydrocarbons are depicted. However, the abundance of lines in the diagram would make it difficult to perceive the main one, and therefore a number of transitions to, it is not shown. The general scheme also allows you to understand the genetic transitions between inorganic and organic substances (the synthesis of hydrocarbons from simple substances and their thermal decomposition), to give a general idea of ​​the cycle of substances using the example of carbon to other elements. You can detail the general scheme using tables of isomeric homologous series of substances, as well as when performing exercise. 16 and 17 (p. 114

Next, we summarize information about intergroup isomers. We note that these include monohydric alcohols and ethers, aldehydes and ketones, phenols and aromatic alcohols, carboxylic acids and esters. The composition of these isomers, as well as singly presented substances in the course (ethylene glycol and unsaturated acids), can be expressed by general formulas. When analyzing such formulas, we identify signs of the complication of substances, determine the place of each group in the genetic chain and reflect this in the general scheme. We carry out its concretization in the lesson and at home when performing ex. 27, 28, 29, 30, 33, 37 (pp. 140-141).

We pose the problem for students about the possibility of further continuation of the general scheme based on the complication of the composition and structure of matter. For this purpose, we pay attention to the composition of fats: the molecule contains six oxygen atoms, based on the formulas of hexatomic alcohol (p. 154), glucose and its isomers (p. 152--156), students derive their general formulas. We also carry out a higher form of work, when the students themselves draw up schemes of the genetic connection between substances and specify them. When analyzing the general scheme, we strive for students to note the relative nature of the relationships between substances reflected in it. We also invite students to prove that the general scheme can be continued, since the path of knowledge does not end with what has been studied.

Tsybina Lyubov Mikhailovna Chemistry teacher Lesson summary.

Lesson summary on the topic: “Genetic connection between the main classes of organic compounds. Problem solving.

Class: Grade 11

Target: create conditions for the systematization and deepening of students' knowledge about the relationship of organic substances according to the scheme: composition - structure - properties of substances and the ability to solve calculation problems.

Tasks:

Educational:

    Generalization and deepening of students' knowledge about the relationship of composition - structure - properties of organic substances on the example of hydrocarbons and oxygen-containing homologous series.

    Expanding the general cultural horizons of students

Developing:

    Development of skills to analyze, compare, draw conclusions, establish a causal genetic relationship between organic substances.

    To be able to choose the right algorithm for solving the calculation problem.

Educational:

    Disclosure of the worldview idea about the relationship of the composition, structure, properties of substances; education of an intellectually developed personality; fostering a culture of communication.

    Be able to work according to the algorithm and with additional literature.

Lesson type:

    for the didactic purpose: a lesson in the systematization of knowledge;

    according to the method of organization: generalizing with the assimilation of new knowledge (combined lesson).

Learning technology:

    problem learning;

    information and communication

Methods used in the lesson:

    explanatory and illustrative:
    - face-to-face conversation
    - explanation of the teacher.

    table schemas, algorithms

    practical:
    - Drawing up schemes of transformations and their implementation.

    deductive:
    - from the known to the unknown;
    - from simple to complex.

Types of control:

    current Poll,

    card work.

    Used educational technologies:

    Informational

    Technology of actualization of personal experience

    Technology of orientation to the cognitive development of the individual

Conduct form : a combination of conversation with illustrative explanatory material, independent activity of students.

Equipment: computer, algorithm for solving the calculation problem.

Lesson plan


Lesson plan


Tasks


I


Organizing time


Prepare students for the lesson.


II


Updating of basic knowledge

"Brainstorm"

(review of the studied material)


Prepare students for learning new material. Reviewing previously learned topics to identify gaps in knowledge and to address them. Improve knowledge and skills, prepare for the perception of new material.


III


Learning new material

    genetic connection;

    genetic series of hydrocarbons and its varieties;

    genetically a number of oxygen-containing hydrocarbons and its varieties.


Develop the ability to generalize facts, build analogies and draw conclusions.

To develop students' ability to chemical prediction and the ability to solve calculation problems using genetic relationships.

Develop environmental thinking.

Development of a culture of communication, the ability to express one's views and judgments, and rational ways to solve a calculation problem.


IV


Consolidation of acquired knowledge


Repetition, reproduction of learned material.

Development of this material on assignments in the UNT format.


V


Summing up the lesson


Perception of a sense of responsibility for the acquired knowledge. Evaluation of students' activities in the lesson. Reflection. Putting marks.


VI


Homework

    Textbook: Chemistry for grade 11 A. Temirbulatova N. Nurakhmetov, R. Zhumadilova, S. Alimzhanova. §10.6 p.119(23,26), p.150(18),

    Workbook exercise 107 a), b) p.22.

1 stage of the lesson

Organizational. Announcement of the topic of the lesson. Updating of basic knowledge.

What does the concept mean"genetic connection"?
The transformation of substances of one class of compounds into substances of other classes;

genetic connection called the connection between substances of different classes, based on their mutual transformations and reflecting the unity of their origin, that is, the genesis of substances.
The key point of the lesson is the creation of a problem situation. To do this, I use a problem-search conversation, which encourages students to make assumptions, express their point of view, causes a clash of ideas, opinions, judgments.
The main task is to point out to students the insufficiency of their knowledge about the object of knowledge, as well as methods of action to complete the task proposed to them.

To compare means to choose, first of all, the criteria for comparison. Please tell us what criteria you think we should compare. Students answer:

    Chemical properties of substances;

    The possibility of obtaining new substances;

    The relationship of substances of all classes of organic compounds.

2 stage lesson

Brainstorming” – frontal conversation with the class:

    What classes of organic compounds do you know?

    What is the peculiarity in the structure of these classes of compounds?

    How does the structure of a substance affect its properties?

    What basic formulas do you know that can be used to solve a calculation problem?

    Using knowledge about the structure of organic substances, the characteristics of their general formulas, students independently write down the basic formulas and predict the possible chemical properties of organic substances.

    3 stage lesson

    Implementation of the genetic link of organic compounds

First option: ethanol ethylene ethane chloroethane ethanol acetaldehyde carbon dioxide

second option: methane → acetylene → ethanal → ethanol → bromoethane → ethylene → carbon dioxide

Third option: acetylene→ethanal→ethanol→bromoethane→ethylene→ethanol→ethyl acetate

work at the blackboard on cards: solving a calculation problem

Task - 1: 6 kg of methyl formate were obtained from methane. Write the corresponding reaction equations. Calculate how much methane was consumed?

Task - 2: How much ethyl acetate can be obtained by reacting 120 g of acetic acid and 138 g of ethanol if the yield of the reaction product is 90% of theoretical?

Task - 3: Oxidized 2 mol of methanol. The resulting product was dissolved in 200 g of water. Calculate the content of methanal in the solution (in%)?

The correct solution of calculation problems is designed on a smartboard.

General conclusion :

We highlight the features that characterize the genetic series of organic substances:

    Substances of different classes;

    Different substances are formed by one chemical element, i.e. represent different forms of existence of one element;

    Different substances of the same homologous series are connected by mutual transformations.

    Knowledge of the genetic relationship between different classes of organic substances allows us to select convenient and economical methods for the synthesis of substances from available reagents.

4th stage of the lesson

Repetition, reproduction of learned material. Development of this material on assignments in the UNT format. p.119(23); Workbook exercise 107 a), b) p.22.

    Short homework tutorial:§10.6 p.119(23,26), p.150(18),

Stage 5 lesson

Summarizing. Reflection.

Students answer the questions:

What new concepts were learned in the lesson?

What questions caused difficulties? Etc.

The teacher grades those students who showed good and excellent knowledge during the lesson were active.

>> Chemistry: Genetic relationship between classes of organic and inorganic substances

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. We single out the most characteristic features of such series:

1. All substances of this series must be formed by one chemical element.

2. Substances formed by the same element must belong to different classes, that is, reflect different forms of its existence.

3. Substances that form the genetic series of one element must be connected by mutual transformations. On this basis, one can distinguish between complete and incomplete genetic series.

Summarizing the above, we can give the following definition of the genetic series:
Genetic refers to a number of substances of representatives of different classes, which are compounds of one chemical element, connected by mutual transformations and reflecting the common origin of these substances or their genesis.

genetic connection - the concept is more general than the genetic series. which is, albeit a vivid, but particular manifestation of this connection, which is realized in any mutual transformations of substances. Then, obviously, the first series of substances targeted in the text of the paragraph fits this definition.

To characterize the genetic relationship of inorganic substances, we consider three types of genetic series:

II. The genetic series of a non-metal. Similarly to the metal series, the non-metal series 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: in order to obtain a simple substance from a window compound of an element, you need to take its most reduced compound for this purpose, for example, the volatile hydrogen compound of a non-metal.

III. The genetic series of the metal, to which the amphoteric oxide and hydroxide correspond, is very rich in sayases. since they exhibit, depending on the conditions, either the properties of an acid or the properties of a base. For example, consider the genetic series of zinc:

In organic chemistry, one should also distinguish between a more general concept - a genetic connection and a more particular concept of a genetic series. If the basis of the genetic series in inorganic chemistry is formed by 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 the largest number of classes of compounds:

Each number above the arrow corresponds to a specific reaction equation (the reverse reaction equation is indicated by a number with a dash):

Iodine definition of the genetic series does not fit the last transition - a product is formed not with two, but with many carbon atoms, but with its help, genetic bonds are most diversely represented. And finally, we will give examples of the genetic connection 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.

Let us take the opportunity to repeat the names of the reactions corresponding to the proposed transitions:
1. Limestone firing:

1. Write down the reaction equations illustrating the following transitions:

3. In the interaction of 12 g of saturated monohydric alcohol with sodium, 2.24 liters of hydrogen (n.a.) were released. Find the molecular formula of alcohol and write down the formulas of the possible isomers.

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