Genetic relationship between classes of organic compounds. On the question of the genetic relationship between organic compounds
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.
General lesson
Lesson Objectives:
Ensure that students learn about the genetic relationship between classes of organic compounds;
Development of independent thinking skills;
To create conditions for the formation of skills of independent and team work.
Lesson objectives:
To continue the formation of students' ability to apply previously acquired knowledge;
Development of logical thinking;
Development speech culture students;
Development of cognitive interest in the subject.
During the classes:
1. Introduction.
2. Warm up.
3. Quiz: "Guess the substance."
4. Drawing up a genetic chain.
5. Homework.
Introduction. Knowing the chemistry of functional groups, possible ways their substitutions, the conditions for their transformations, it is possible to plan organic synthesis, moving from relatively simple compounds to more complex ones. AT famous book Carrol's "Alice in Wonderland" Alice addresses the Cheshire Cat: "Tell me, please, where should I go?" To which the Cheshire Cat reasonably remarks: "It depends a lot on where you want to go." How can this dialogue be connected with a genetic connection? We will try, using knowledge of chemical properties organic compounds, to carry out transformations from the simplest representatives of alkanes to high-molecular compounds.
I. Warm up.
1. Repeat the classes of organic compounds.
2. What are the structure of the series of transformations?
3. Solution of 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."
The task for the students is to identify the substance 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 swamp gas, it is the basis of natural gas, a valuable and affordable raw material for the synthesis of many substances. (Methane)
Teacher's Addendum: One interesting 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 supplied to a tungsten plate heated to 2500 C, on which the resulting crystals settled.
2) This substance is called - lighting gas. This gas was initially used mainly for lighting: street lamps, theater ramps, camping and mining lamps. Old bikes had carbide lights. Water entered a vessel filled with calcium carbide, and the resulting gas entered the lamp through a special nozzle, 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) It was found by special experiments that with a content of this substance in the air of about 0.1%, vegetables and fruits ripen faster. This substance is called a plant growth regulator. (Ethylene)
Teacher's addition: it turns out that ethylene is needed for flowering of pineapples. Oil is burned on the plantations, and small quantities the ethylene produced is enough to produce a crop. And at home, you can use a ripe banana, which also releases ethylene. By the way, ethylene can transmit information. Kudu antelopes feed on acacia leaves, which produce tannin. This substance gives the leaves a bitter taste, and in high concentrations it is poisonous. Antelopes can choose leaves from low content tannin, but in extreme conditions they eat any and die. It turns out that the leaves eaten by antelopes emit ethylene, which serves as a signal for neighboring acacias, and after half an hour their leaves intensively produce tannin, which leads to the death of antelopes.
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 exactly this 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 instantaneous formation of a large volume of gas from a small volume of liquid or solid. The pressure of expanding gases is the destructive force of an explosion. (Trinitrotoluene)
III. Compilation of the genetic chain.
Group work. The class is divided into groups of 4 people.
The task for the groups is to make a series of transformations using as many substances guessed in the quiz as possible. The assignment is offered on time. After completion, the task is checked at the blackboard.
At the end of the lesson, evaluate student responses.
Consider the genetic series organic matter, in which we include largest number connection classes:
Each number above the arrow corresponds to a specific reaction equation (the reverse reaction equation is indicated by a number with a dash):
IV. Homework: Make a genetic series of transformations, including at least five classes of organic compounds.
Alice (in Wonderland to the Cheshire cat): - Tell me, where should I go from here? Alice (in Wonderland to the Cheshire cat): - Tell me, where should I go from here? Cheshire cat: - It depends on where you want to come? Cheshire cat: - It depends on where you want to come? 2
Synthesis strategy “I want to sing the praises of the creation of molecules – chemical synthesis… …I deeply believe that this is art. And at the same time, synthesis is logic.” Roald Hoffmann (Nobel Prize in Chemistry 1981) Choice of starting materials Construction of the carbon backbone of a molecule Introduction, removal or replacement functional group Group protection Stereo selectivity 5
CO + H 2 Ru, 1000 atm, C ThO 2, 600 atm, C Cr 2 O 3, 30 atm, C Fe, 2000 atm, C ZnO, Cr 2 O 3, 250 atm, C CH 3 OH 6
С n H 2n+2 Scheme of the formation of σ-bonds in a methane molecule Models of methane molecules: ball-and-stick (left) and scale (right) СH4СH4СH4СH4 Tetrahedral structure sp 3 -hybridization σ - bonds homolytic bond breaking X: Y homolytic bond breaking S R) substitution (S R) Combustion Dehydrogenation S - eng. substitution Prediction of reactivity 7
CH 3 Cl - METHYL CHLORIDE CH 4 METHANE C - SOOT C 2 H 2 - ACETYLENE CH 2 Cl 2 - DICHLOROMETHANE CHCl 3 - TRICHLOROMETHANE CCl 4 - TETRACHLOROMETHANE H 2 - HYDROGEN SYNTHESIS GAS CO + H 2 SYNTHESIS GAS CO + H 2 Cl 2, hγ Chlorination С pyrolysis Н 2 О, Ni, C О 2 conversion, Oxidation СH 3 OH – METHANOL HCHO – METHANAL solvents Benzene СHFCl 2 freon HCOOH - formic acid Synthetic gasoline SYNTHESIS BASED ON METHANE 8 СH 3 NO 2 – NITROMETHANE СCl 3 NO 2 chloropicrin CH 3 NH 2 methylamine HNO 3, C Nitration
C n H 2n Scheme of formation of σ-bonds with the participation of sp 2 -hybrid clouds of a carbon atom Scheme of formation of π-bonds with the participation of p-clouds of a carbon atom Model of an ethylene molecule Electrophilic addition reactions (A E) Polymerization Polymerization Oxidation OxidationCombustion 2 – hybridization of σ– and σ – and π – bonds Eb (C = C) = 611 kJ/mol Eb (C – C) = 348 kJ/mol A – English. addition – addition Prediction of reactivity 9
C 2 H 4 Ethylene Polymerization H 2 O, H + Hydration Cl 2 Chlorination Oxidation ETHYL ALCOHOL C 2 H 5 OH ETHYLNE ALCOHOL C 2 H 5 OH 2 O O 2, PdCl 2, CuCl 2 HDPE HDPE C MPa 80 0 C, 0.3 MPa, Al(C 2 H 5) 3, TiCl 4 SKD LDPE LDPE Butadiene-1,3 (divinyl) Acetic acid Dioxane Acetic acid 10
С n H 2n-2 Scheme of the formation of σ-bonds and π-bonds with the participation of sp-hybrid clouds of the carbon atom Models of the acetylene molecule electrophilic addition reactions (A E) oxidation oxidation di-, tri- and tetramerizations di-, tri- and tetramerizations combustion combustion reactions involving an "acidic" hydrogen atom Linear structure (180 0) (cylindrical distribution of electron density) sp - hybridization σ– and 2 σ - and 2π - bonds Prediction of reactivity 11
C2H2C2H2 HCl, Hg 2+ H 2 O, Hg 2+ Kucherov reaction C act, C trimerization SYNTHESIS BASED ON ACETYLENE ACETATE ALDEHYDE Acetic aldehyde СuCl 2, HCl, NH 4 Cl ROH dimerization Acetic acid BENZENE SKD Divinyl Chloroprene SC Chloroprene EVNYLACETYLENE VINYLS ethersPolyvinyl chloride VINYL CHLORIDE HCN, СuCl, HCl, 80 0 C ACRYLONITRILE Fibers 12
13
Scheme of the formation of π-bonds in the benzene molecule Delocalization of electron density in the benzene molecule Scheme of the formation of σ-bonds in the benzene molecule with the participation of sp 2 - hybrid orbitals of carbon atoms С n H 2n-6 Prediction of reactivity Planar sp 2 molecule - hybridization of σ– and σ – and π – bonds Aromatic structure Electrophilic substitution reactions (S E) Radical addition reactions (А R) Radical addition reactions (А R) Combustion 14 M. Faraday (1791–1867) English physicist and a chemist. Founder of electrochemistry. Discovered benzene; first received in a liquid state chlorine, hydrogen sulfide, ammonia, nitrogen oxide (IV).
BENZENE H 2 /Pt, C hydrogenation SYNTHESIS BASED ON BENZENE NITROBENZENE NITROBENZENE Сl 2, FeCl 3 chlorination of HNO 3, H 2 SO 4 (conc) nitration of CH 3 Cl, AlCl 3 alkylation CHLOROBENZENE Aniline TOLUENE TOLUENE Benzoic acid 2,4,6- trinitrotoluene STYRENE STYRENE Polystyrene 1. CH 3 CH 2 Cl, AlCl 3 Alkylation 2. – H 2, Ni dehydrogenation CH 2 =CH-CH 3, AlCl 3 alkylation fifteen
SYNTHESIS BASED ON METHANOL CH 3 OH VINYL METHYL ETHER VINYL METHYL ETHER DIMETHYLANILINE C 6 H 5 N(CH 3) 2 DIMETHYLANILINE C 6 H 5 N(CH 3) 2 3 METHYLAMINE CH 3 NH 2 METHYLAMINE CH 3 NH 2 VINYL ACETATE METHYL CHLORIDE CH 3 Cl METHYL CHLORIDE CH 3 Cl FORMALDEHYDE CuO, t HCl NH 3 METHYLTHIOL CH 3 SH METHYLTHIOL CH 3 SH H 2 S, t C 6 H 5 NH 2 + CO 16 H +, t
Formaldehyde syntheses methanol CH 3 oh methanol CH 3 oh paraformaldehyde resins phenolformaldehyde resins trioxan primary alcohols of carbamide resins of ureotropins (hexmetyleteetramine) urotropin (hexmetylentetramin) muravyic acid Muravic acid hexogenic acid [O] [O] [O] [O] [O] [O] [O] [O] [O] [O] [O] [OAM] [O] SUBED. Butlerov 18
CxHyOzCxHyOz Genetic linkage of oxygen-containing organic compounds ALDEHYDES ALDEHYDES CARBOXY ACIDS CARBOXY ACIDS KETONES KETONES ESTERS ETHERS ETHERS ALCOHOLS hydrolysis dehydration hydrogenation oxidation, dehydrogenation esterification esterification oxidation H+, t 
C n H 2n+2 C n H 2n Cycloalkanes Alkenes C n H 2n-2 AlkynesAlkadienes C n H 2n-6 Arenes, benzene
C n H 2n+2 C n H 2n CycloalkanesAlkenes C n H 2n-2 AlkynesAlkadienes Primary Secondary Tertiary C n H 2n-6 Arenes, benzene 12 C n H 2n Cycloalkanes Alkenes C n H 2n-2 AlkynesAlkadienes α 23
C n H 2n+2 C n H 2n CycloalkanesAlkenes C n H 2n-2 AlkynesAlkadienes Primary Secondary Tertiary C n H 2n-6 Arenes, benzene 12 C n H 2n Cycloalkanes Alkenes C n H 2n-2 AlkynesAlkadienes
C n H 2n+2 C n H 2n CycloalkanesAlkenes C n H 2n-2 AlkynesAlkadienes Primary Secondary Tertiary C n H 2n-6 Arenes, benzene Polyethylene Polypropylene 12 C n H 2n Cycloalkanes Alkenes C n H 2n-2 AlkynesAlkadienes Rubber Catalyst Ziegler - Natta (1963) 25
C n H 2n+2 C n H 2n CycloalkanesAlkenes C n H 2n-2 AlkynesAlkadienes Primary Secondary Tertiary C n H 2n-6 Arenes, benzene Polyethylene Polypropylene Rubbers Fats Phenolformaldehyde resins 12 C n H 2n Cycloalkanes Alkenes C n H 2n- 2 AlkynesAlkadienes
C n H 2n+2 C n H 2n CycloalkanesAlkenes C n H 2n-2 AlkynesAlkadienes Primary Secondary Tertiary C n H 2n-6 Arenes, benzene Polyethylene Polypropylene Rubbers Fats Synthetic dyes Phenol formaldehyde resins 12 C n H 2n Cycloalkanes Alkenes C n H 2n-2 AlkynesAlkadienes
Application of aniline ANILIN N.N. Zinin (1812 - 1880) medicinal substances Dyes Explosives Streptocide NorsulfazolFthalazol Obtaining aniline - Zinin reaction Tetryl Aniline yellow Nitrobenzene p-Aminobenzoic acid (PABA) Sulfanilic acid indigo Paracetamol 28
C n H 2n+2 C n H 2n Cycloalkanes Alkenes C n H 2n-2 Alkynes Alkadienes Primary Secondary Tertiary C n H 2n-6 Arenes, benzene Polyethylene Polypropylene Rubber Fats Synthetic dyes Phenol-formaldehyde resins Proteins 12 C n H 2n Cycloalkanes Alkenes C n H 2n-2 Alkynes Alkadienes
AT school course 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 related to the fundamental concepts of chemistry -- chemical element, chemical reaction, homology, isomerism, 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, in practice, 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, not only the method of obtaining the product is clarified, but also the conditions for conducting 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 , their influence on surrounding a person Wednesday. 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 at integrated approach to him does not act as a separate, 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 entire 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 different structure. 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 makes it possible to understand the genetic transitions between inorganic and organic substances (the synthesis of hydrocarbons from simple substances and their thermal decomposition), give general idea about the cycle of substances on 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 these purposes, 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 carry out more high form work, when students themselves draw up schemes of the genetic relationship between substances and concretize 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.
74. Write equations and name the reaction products according to the scheme:
75. Write equations and name the reaction products according to the scheme:
76. Write equations and name the reaction products according to the scheme:
77. Write equations and name the reaction products according to the scheme:
78. Write equations and name the reaction products according to the scheme:
79. Write equations and name the reaction products according to the scheme:
80. Write equations and name the reaction products according to the scheme:
81. Write equations and name the reaction products according to the scheme:
82. Write equations and name the reaction products according to the scheme:
83. Write equations and name the reaction products according to the scheme:
84. Write equations and name the reaction products according to the scheme:
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87. Write equations and name the reaction products according to the scheme:
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90. Write equations and name the reaction products according to the scheme:
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93. Write equations and name the reaction products according to the scheme:
94. Write equations and name the reaction products according to the scheme:
95. Write equations and name the reaction products according to the scheme:
96. Write equations and name the reaction products according to the scheme:
97. Write equations and name the reaction products according to the scheme:
98. Write equations and name the reaction products according to the scheme:
99. Write equations and name the reaction products according to the scheme:
100. Write equations and name the reaction products according to the scheme:
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 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 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 products of the interaction 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 correct. 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 uric acid two-base, not three-base?
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 character 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 connection
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 into 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 monosaccharide.
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 schemes of successive 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.
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