Lesson topic “Genetic relationship of hydrocarbons, alcohols, aldehydes and ketones” Goal To develop the ability to compile structural formulas using this information. To develop the skill of implementing chains of transformations of organic substances. Improve knowledge of the classification and nomenclature of organic substances.

Activity program “Drawing up a structural formula of a substance using this information” 1) Translate this information into the language of diagrams. 2) Guess the connection class. 3) Establish the class of the compound and its structural formula. 4) Write the equations for the reactions that occur.

Activity program: “Implementation of chains of transformations” 1). Number the chemical reactions. 2).Determine and label the class of each substance in the chain of transformations. 3).Analyze the chain: A) Write the formulas of the reagents and reaction conditions above the arrow; B) Under the arrow, write the formulas of additional products with a minus sign. 4).Write the reaction equations: A) Arrange the coefficients; B) Name the reaction products.

Classification of organic compounds according to the structure of the carbon chain 1. Depending on the nature of the carbon skeleton, acyclic (linear and branched and cyclic) compounds are distinguished. Acyclic (aliphatic, non-cyclic) compounds - compounds that have an open linear or branched carbon chain are often called normal. Cyclic compounds - compounds, containing molecules closed in the CA cycle

Classification of individual carbon atoms In the carbon skeletons themselves, it is customary to classify individual carbon atoms according to the number of carbon atoms chemically bonded to it. If a given carbon atom is connected to one carbon atom, then it is called primary, with two - secondary, three - tertiary and four - quaternary. In carbon skeletons themselves, it is customary to classify individual carbon atoms according to the number of carbon atoms chemically bonded to them. If a given carbon atom is connected to one carbon atom, then it is called primary, with two - secondary, three - tertiary and four - quaternary. What is the name of the carbon atom shown: What is the name of the carbon atom shown: a) inside the circle _________________; b) inside the square __________________; c) inside the heart __________________; d) inside the triangle _________________;

15) hydrogen bond between molecules.
Physical properties of alcohols.
1. The strength of a hydrogen bond is significantly less than the strength of a conventional covalent bond (about 10 times).
2. Due to hydrogen bonds, alcohol molecules become associated, as if stuck to each other; additional energy must be expended to break these bonds so that the molecules become free and the substance becomes volatile.
3. This is the reason for the higher boiling point of all alcohols compared to the corresponding hydrocarbons.
4. Water with such a small molecular weight has an unusually high boiling point.

40. Chemical properties and application of saturated monohydric alcohols

As substances containing carbon and hydrogen, alcohols burn when ignited, releasing heat, for example:
C2H5OH + 3O2 ? 2СO2 + 3Н2О +1374 kJ,
When burning, they also exhibit differences.
Experience Features:
1) it is necessary to pour 1 ml of various alcohols into porcelain cups and set the liquid on fire;
2) it will be noticeable that alcohols - the first representatives of the series - are easily flammable and burn with a bluish, almost non-luminous flame.
Features of these phenomena:
a) from the properties determined by the presence of the OH functional group, it is known about the interaction of ethyl alcohol with sodium: 2C2H5OH + 2Na? 2C2H5ONa + H2;
b) the product of hydrogen substitution in ethyl alcohol is called sodium ethoxide, it can be isolated after the reaction in solid form;
c) other soluble alcohols react with alkali metals, which form the corresponding alcoholates;
d) the interaction of alcohols with metals occurs with ionic splitting of the polar O-N connections;
e) in such reactions, alcohols exhibit acidic properties - the elimination of hydrogen in the form of a proton.
The decrease in the degree of dissociation of alcohols compared to water can be explained by the influence of the hydrocarbon radical:
a) the radical’s displacement of the electron density of the C-O bond towards the oxygen atom leads to an increase in the partial negative charge on the latter, while it holds the hydrogen atom more firmly;
b) the degree of dissociation of alcohols can be increased if a substituent is introduced into the molecule, attracting electrons of a chemical bond.
This can be explained as follows.
1. The chlorine atom shifts the electron density of the Cl-C bond towards itself.
2. The carbon atom, thereby acquiring a partial positive charge, in order to compensate for it, shifts the electron density in its direction S-S connections.
3. For the same reason, the electron density of the C-O bond is slightly shifted towards the carbon atom, and the density of the O-H bond is shifted from the hydrogen atom to oxygen.
4. The possibility of removing hydrogen in the form of a proton increases from this, and the degree of dissociation of the substance increases.
5. In alcohols, not only the hydroxyl hydrogen atom, but also the entire hydroxyl group can enter into chemical reactions.
6. If you heat ethyl alcohol with a hydrohalic acid, for example hydrobromic acid, in a flask with a refrigerator attached to it (to form hydrogen bromide, take a mixture of potassium bromide or sodium bromide with sulfuric acid), then after a while you will notice that heavy liquid – bromoethane

41. Methanol and ethanol

Methyl alcohol, or methanol, its features:
1) structural formula – CH3OH;
2) it is a colorless liquid with a boiling point of 64.5 °C;
3) poisonous (can cause blindness, death);
4) in large quantities methyl alcohol is obtained by synthesis from carbon monoxide (II) and hydrogen at high pressure (20–30 MPa) and high temperature (400 °C) in the presence of a catalyst (about 90% ZnO and 10% Cr2O3): CO + 2H2 ? CH3OH;
5) methyl alcohol is also formed during the dry distillation of wood, which is why it is also called wood alcohol. It is used as a solvent, as well as for the production of other organic substances.
Ethyl (wine) alcohol, or ethanol, its features:
1) structural formula – CH3CH2OH;
2) boiling point 78.4 °C;
3) ethanol is one of the most important starting materials in the modern organic synthesis industry.
Methods for producing ethanol:
1) for production, various sugary substances are used (grape sugar, glucose, which is converted into ethyl alcohol by “fermentation”). The reaction proceeds according to the scheme:
C6H12O6(glucose) ? 2C2H5OH + 2CO2.
2) glucose is found in free form, for example, in grape juice, the fermentation of which produces grape wine with an alcohol content of 8 to 16%;
3) the starting product for producing alcohol can be the polysaccharide starch, which is found, for example, in potato tubers, grains of rye, wheat, and corn;
4) to convert it into sugary substances (glucose), starch is first subjected to hydrolysis.
To do this, flour or chopped potatoes are boiled hot water and upon cooling, malt is added to it.
Malt- These are sprouted, then dried and ground with water grains of barley.
Malt contains diastase, which acts catalytically on the process of starch saccharification.
Diastasis– it is a complex mixture of enzymes;
5) upon completion of saccharification, yeast is added to the resulting liquid, under the action of whose enzymes (zymase) alcohol is formed;
6) it is distilled and then purified by repeated distillation.
Currently, the polysaccharide cellulose (fiber), which forms the main mass of wood, is also subjected to saccharification.
To do this, cellulose undergoes hydrolysis in the presence of acids (for example, sawdust at 150–170 °C are treated with 0.1–5% sulfuric acid under a pressure of 0.7–1.5 MPa).

42. Alcohols as derivatives of hydrocarbons. Industrial synthesis of methanol

Genetic relationship between alcohols and hydrocarbons:
1) alcohols can be considered as hydroxyl derivatives of hydrocarbons;
2) they can also be classified as partially oxidized hydrocarbons, since, in addition to carbon and hydrogen, they also contain oxygen;
3) it is quite difficult to directly replace a hydrogen atom with a hydroxyl group or introduce an oxygen atom into a hydrocarbon molecule;
4) this can be done through halogen derivatives.
For example, to obtain ethyl alcohol from ethane, you must first obtain bromoethane:
C2H6 + Br ? С2Н5Вr + НВr.
And then convert bromoethane into alcohol by heating with aqueous alkali:
C2H5 Br + H OH? C2H5OH + HBr;
5) alkali is needed to neutralize hydrogen bromide and eliminate the possibility of its reaction with alcohol;
6) in the same way, methyl alcohol can be obtained from methane: CH4? CH3Br ? CH3OH;
7) alcohols are associated genetically and with unsaturated hydrocarbons.
For example, ethanol is produced by the hydration of ethylene:
CH2=CH2? H2O=CH3-CH2-OH.
The reaction occurs at a temperature of 280–300 °C and a pressure of 7–8 MPa in the presence of orthophosphoric acid as a catalyst.
Industrial synthesis of methanol, its features.
1. Methyl alcohol cannot be obtained by hydration of an unsaturated hydrocarbon.
2. It is obtained from synthesis gas, which is a mixture of carbon (II) monoxide with hydrogen.
Methyl alcohol is obtained from synthesis gas by the reaction:
CO + 2H2? CH3OH + Q.
Characteristic features of the reaction.
1. The reaction proceeds in the direction of decreasing the volume of the mixture, while a shift in equilibrium towards the formation of the desired product will be facilitated by an increase in pressure.
2. For the reaction to proceed at a sufficient speed, a catalyst and elevated temperature are required.
3. The reaction is reversible; the starting substances do not react completely when passing through the reactor.
4. In order to use them economically, the alcohol that is formed must be separated from the reaction products, and the unreacted gases must be sent back to the reactor, i.e., a circulation process must be carried out.
5. In order to save energy costs, the waste products of the exothermic reaction must be used to heat the gases that go into synthesis.

43. The concept of pesticides

Pesticides (pesticides)- These are chemical means of combating microorganisms that are harmful or undesirable from an economic or health point of view.
The most important types of pesticides are the following.
1. Herbicides. Main properties:
a) these are preparations for weed control, which are divided into arboricides and algaecides;
b) these are phenoxy acids, derivatives of benzoic acid;
c) these are dinitroanilines, dinitrophenols, halophenols;
d) these are many heterocyclic compounds;
e) the first synthetic organic herbicide – 2-methyl-4,6-dinitrophenol;
f) other widely used herbicides – atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine); 2,4-dichlorophenoxyacetic acid.
2. Insecticides. Peculiarities:
a) these are substances that destroy harmful insects; they are usually divided into antifeeding agents, attractants and chemosterilizers;
b) these include organochlorine, organophosphorus substances, preparations that contain arsenic, sulfur preparations, etc.;
c) one of the most well-known insecticides is dichlorodiphenyl-trichloromethylmethane (DDT);
d) are widely used in agriculture and in everyday life insecticides such as hexachlorane (hexachlorocyclohexane).
3. Fungicides.
Characteristic features of fungicides:
a) these are substances to combat fungal plant diseases;
b) various antibiotics and sulfonamide drugs are used as fungicides;
c) one of the simplest fungicides in chemical structure is pentachlorophenol;
d) most pesticides have poisonous properties not only against pests and pathogens;
e) if handled improperly, they can cause poisoning of people, domestic and wild animals or the death of cultivated crops and plantings;
f) pesticides must be used very carefully, strictly following the instructions for their use;
g) in order to minimize the harmful effects of pesticides on the environment, you should:
– use substances with higher biological activity and, accordingly, apply them in smaller quantities per unit area;
– use substances that are not stored in the soil, but decompose into harmless compounds.

44. Polyhydric alcohols

Features of the structure of polyhydric alcohols:
1) contain in the molecule several hydroxyl groups connected to a hydrocarbon radical;
2) if two hydrogen atoms are replaced by hydroxyl groups in a hydrocarbon molecule, then it is a dihydric alcohol;
3) the simplest representative of such alcohols is ethylene glycol (ethanediol-1,2):
CH2(OH) – CH2(OH);
4) in all polyhydric alcohols, hydroxyl groups are located at different carbon atoms;
5) to obtain an alcohol in which at least two hydroxyl groups would be located on one carbon atom, many experiments were carried out, but it was not possible to obtain alcohol: such a compound turns out to be unstable.
Physical properties of polyhydric alcohols:
1) the most important representatives of polyhydric alcohols are ethylene glycol and glycerin;
2) these are colorless, syrupy liquids with a sweetish taste;
3) they are highly soluble in water;
4) these properties are also inherent in other polyhydric alcohols, for example ethylene glycol is poisonous.
Chemical properties of polyhydric alcohols.
1. As substances that contain hydroxyl groups, polyhydric alcohols have similar properties to monohydric alcohols.
2. When hydrohalic acids act on alcohols, the hydroxyl group is replaced:
CH2OH-CH2OH + H CI ? CH2OH-CH2CI + H2O.
3. Many alcohols also have special properties: polyhydric alcohols exhibit more acidic properties than monohydric alcohols and easily form alcoholates not only with metals, but also with heavy metal hydroxides. Unlike monohydric alcohols, polyhydric alcohols react with copper hydroxide, giving complexes blue(qualitative reaction to polyhydric alcohols).

4. Using the example of polyhydric alcohols, one can be convinced that quantitative changes transform into qualitative changes: the accumulation of hydroxyl groups in the molecule resulted, as a result of their mutual appearance, in alcohols of new properties compared to monohydric alcohols.
Methods for producing and using polyhydric alcohols: 1) like monohydric alcohols, polyhydric alcohols can be obtained from the corresponding hydrocarbons through their halogen derivatives; 2) the most common polyhydric alcohol is glycerin, it is obtained by the breakdown of fats, and now increasingly in a synthetic way from propylene, which is formed during the cracking of petroleum products.

45. Phenols

Hydroxyl derivatives, which contain functional groups in side chain, belong to the class of alcohols.
Phenols – these are hydroxyl derivatives aromatic hydrocarbons, in the molecules of which functional groups are associated with the benzene ring.
The simplest phenol is the monoatomic hydroxyl derivative of benzene C6H5OH, which is usually called phenol.
Properties of phenol:
1) this is a crystalline, colorless substance with a characteristic odor; when partially oxidized in air, it often turns pink, and is very fusible;
2) phenol has some similarity in chemical properties with monohydric alcohols;
3) if phenol is slightly heated (until melting) and sodium metal is placed in it, hydrogen is released. In this case, by analogy with alcoholates, sodium phenolate 2С6Н5ОH + 2Nа? 2C6H5ONa + H2;
4) unlike alcoholates, phenolate is obtained if phenol is treated with an alkali solution;
5) in this case, solid phenol is converted into sodium phenolate, which quickly dissolves in water: C6H5OH + NaOH? C6H5ONa + H2O;
6) taking into account ionic bond splitting, the equation takes the following form: C6H5O(H) + Na++ OH-? [C6H5O]-+ Na++ H2O.
Reaction feature:
a) in these reactions the acidic properties of phenol are manifested;
b) the degree of dissociation of phenol is greater than that of water and saturated alcohols, therefore it is also called carbolic acid;
3) phenol is a weak acid, even carbonic acid is stronger, it can displace phenol from sodium phenolate.
Methods of application and production of phenol
1. As a substance that kills many microorganisms, phenol has long been used in the form of an aqueous solution to disinfect rooms, furniture, surgical instruments, etc.
2. It is used to obtain dyes and many medicinal substances.
3. A particularly large amount of it is consumed in the production of widespread phenol-formaldehyde plastics.
4. For industrial needs, primarily phenol is used, which is obtained from coal tar.
But this source cannot fully satisfy the need for phenol.
Therefore, it is also produced in large quantities using synthetic methods from benzene.
Aldehydes- these are organic substances whose molecules contain a functional group of atoms connected to a hydrocarbon radical.

46. ​​Aldehydes and their chemical properties

Aldehydes are organic substances whose molecules contain a carbonyl group, which is bonded to at least one hydrogen atom and a hydrocarbon radical.

The chemical properties of aldehydes are determined by the presence of a carbonyl group in their molecule. At the site of the double bond in the carbonyl group molecule, addition reactions can occur. If, for example, formaldehyde vapor together with hydrogen is passed over a heated nickel catalyst, hydrogen is added: formaldehyde is reduced to methyl alcohol. The polar nature of the double bond also determines other reactions of aldehydes, such as the addition of water.
Features of the water addition reaction: a) a hydroxyl group is attached to the carbon atom of the carbonyl group, which carries a partial positive charge, due to the electron pair of the oxygen atom; b) the electron pair of the α-bond goes to the oxygen atom of the carbonyl group and a proton is added to the oxygen;
The addition reaction is characterized by:
1) hydrogenation (reduction) with the formation of primary alcohols RCH2OH.
2) addition of alcohols to form hemiacetals R-CH (OH) – OR.
In the presence of a catalyst - hydrogen chloride HCl and in excess of alcohol, acetals RCH (OR)2 are formed;
3) addition of sodium hydrosulfite NaHSO3 with the formation of hydrosulfite derivatives of aldehydes.
Features of the aldehyde oxidation reaction: react with an ammonia solution of silver (I) oxide and copper (II) hydroxide to form carboxylic acids.
Features of the aldehyde polymerization reaction: 1) linear polymerization is characteristic; 2) characterized by cyclic polymerization (trimerization, tetramerization).
Features of the “silver mirror” reaction: 1) silver appears on the walls of the test tube in the form of a shiny coating; 2) in such a redox reaction, the aldehyde is converted into an acid (with an excess of ammonia, an ammonium salt is formed); 3) silver is released in free form; 4) copper hydroxide Cu(OH)2 can also be used as an oxidizing agent for aldehydes; 3) if an aldehyde solution is added to copper hydroxide and the mixture is heated, the formation of a yellow precipitate of copper (I) hydroxide is observed, which turns into red copper oxide; 4) copper (II) hydroxide oxidizes the aldehyde into an acid, and itself is reduced to copper (I) oxide.
Reactions with ammonia solution of silver (I) oxide and copper (II) hydroxide can serve to detect aldehydes.
Carbonyl compounds can be reduced to alcohols. Aldehydes are reduced to primary alcohols, and ketones are reduced to secondary alcohols. Some methods allow you to reduce the carbonyl group to a methylene group.

47. Application and preparation of aldehydes

Use of aldehydes.
Of the aldehydes, formaldehyde is the most widely used. Features of the use of formaldehyde: it is usually used in the form of an aqueous solution - formalin; many methods of using formaldehyde are based on the property of coagulating proteins; in agriculture, formalin is necessary for seed treatment; formaldehyde is used in the tanning industry; formalin has a tanning effect on skin proteins, making them harder and non-rotting; formalin is also used to preserve biological products; When formaldehyde reacts with ammonia, the well-known medicinal substance methenamine is obtained.
The bulk of formaldehyde is used to produce phenol-formaldehyde plastics, from which the following are made: a) electrical products; b) machine parts, etc. Acetaldehyde (acetic aldehyde) is used in large quantities to produce acetic acid.
In some countries, ethyl alcohol is obtained by reducing acetaldehyde.
Preparation of aldehydes:
1) a general method for producing aldehydes is the oxidation of alcohols;
2) if you heat a copper wire spiral in the flame of an alcohol lamp and lower it into a test tube with alcohol, then the wire, which becomes covered with a dark coating of copper (II) oxide when heated, becomes shiny in alcohol;
3) the smell of aldehyde is also detected.
Using this reaction, formaldehyde is produced industrially.
To obtain formaldehyde, a mixture of methyl alcohol vapor and air is passed through a reactor with a hot copper or silver mesh;
4) in the laboratory preparation of aldehydes, other oxidizing agents, for example potassium permanganate, can be used to oxidize alcohols;
5) When an aldehyde is formed, the alcohol, or alcohol, undergoes dehydrogenation.
Features of the acetylene hydration reaction:
a) first, water is added to acetylene at the site of one?-bond;
b) vinyl alcohol is formed;
c) unsaturated alcohols, in which the hydroxyl group is located at the carbon atom that is connected by a double bond, are unstable and easily isomerize;
d) vinyl alcohol turns into aldehyde:

E) the reaction is easily carried out by passing acetylene into heated water, which contains sulfuric acid and mercury (II) oxide;
f) after a few minutes, an aldehyde solution can be detected in the receiver.
IN recent years A method for producing acetaldehyde by oxidation of ethylene with oxygen in the presence of palladium and copper chlorides has been developed and is becoming widespread.

48. Formaldehyde and acetaldehyde

Structure and properties of formaldehyde: it is a colorless gas with a sharp suffocating odor, poisonous; it is highly soluble in water; an aqueous 40% solution of formaldehyde is called formalin.
Chemical properties of formaldehyde.
Formaldehyde is characterized by oxidation and addition reactions (including polycondensation):
1) oxidation reaction:
a) the oxidation reaction proceeds very easily - aldehydes are capable of removing oxygen from many compounds;
b) when formaldehyde is heated with an ammonia solution of silver oxide (silver oxide is insoluble in water), formaldehyde is oxidized into formic acid HCOOH and silver is reduced. Education "silver mirror" serves as a qualitative reaction to the aldehyde group;
d) aldehydes reduce copper (II) hydroxide to copper (I) hydroxide, which turns into orange copper (I) oxide;
e) the reaction occurs when heated: 2СuОН? Cu2O + H2O;
f) this reaction can also be used for the detection of aldehydes;
2) addition reaction:
a) the addition reaction occurs due to the cleavage of the double bond of the carbonyl group of the aldehyde;
b) the addition of hydrogen, which occurs when a mixture of formaldehyde and hydrogen is passed over a heated catalyst - nickel powder, leads to the reduction of aldehyde into alcohol;
c) formaldehyde also adds ammonia, sodium hydrosulfite and other compounds.
Methods for obtaining formaldehyde:
1) in industry, formaldehyde is obtained from methanol by passing alcohol vapor along with air over a copper catalyst heated to 300 °C: 2CH3OH + O2? 2HCHO + 2H2O;
2) an important industrial method is also the oxidation of methane with air at 400–600 °C in the presence of a small amount of nitrogen oxide as a catalyst: CH4 + O2? CH2O + H2O.
Application of formaldehyde: 1) formaldehyde is used in large quantities for the production of phenol-formaldehyde resins; 2) it serves as a starting material for the production of dyes, synthetic rubber, medicinal substances, explosives etc.
Features of acetaldehyde: acetaldehyde (or acetaldehyde, or ethanal) is a colorless liquid with a pungent odor, highly soluble in water; The addition of hydrogen to acetaldehyde occurs under the same conditions as to formaldehyde.
Features of paraldehyde: this is a liquid that solidifies into a crystalline mass at 12 °C, and when heated in the presence of dilute mineral acids turns into acetaldehyde; has a strong hypnotic effect.

49. Polycondensation reaction. Carbohydrates

Polycondensation is the process of formation of high molecular weight compounds from low molecular weight ones, which is accompanied by the release of by-products (water, ammonia, hydrogen chloride and other substances).
Features of the polycondensation reaction:
1) during polymerization, unlike polycondensation, no release of by-products occurs;
2) polycondensation products (excluding by-products), as well as polymerization products, are called polymers;
3) during a polycondensation reaction, the chain grows gradually: first, the original monomers interact with each other, then the resulting compounds alternately react with molecules of the same monomers, ultimately forming a polymer compound. An example of a polycondensation reaction is the formation of phenol-formaldehyde resins, which are used to make plastics;
4) the reaction occurs when heated in the presence of a catalyst (acid or alkali);
5) in the phenol molecule, the hydrogen atoms are mobile, and the carbonyl group of the aldehyde is capable of addition reactions, while phenol and formaldehyde interact with each other;
6) the resulting compound further reacts with phenol to release a water molecule;
7) the new compound interacts with formaldehyde;
8) this compound condenses with phenol, then again with formaldehyde, etc.;

Tazhibaeva Asemgul Isintaevna

Teacher at Kamennobrod Secondary School

Chemistry lesson in 11th grade

Lesson topic: Genetic relationships between hydrocarbons, alcohols, aldehydes, alcohols, carboxylic acids.

Lesson type: lesson of generalization of knowledge.

Lesson objectives: consolidate, generalize and systematize knowledge on oxygen-containing organic compounds, including on the basis of genetic connections between classes of these substances. Strengthen the ability to predict the chemical properties of unfamiliar organic substances based on knowledge of functional groups. To develop in students demonstrative speech, the ability to use chemical terminology, conduct, observe and describe a chemical experiment. To cultivate the need for knowledge about the substances with which we come into contact in life.

Methods: verbal, visual, practical, problem-search, knowledge control.

Reagents: acetylsalicylic acid (aspirin), water, ferric chloride (III), glucose solution, universal indicator, copper (II) sulfate solution, sodium hydroxide solution, egg white, ethanol, 1-butanol, acetic acid, stearic acid.

Equipment: computer, screen, projector, table “Classification of oxygen-containing organic substances”, supporting note “Functional group determines the properties of a substance”, mortar and pestle, glass rod, alcohol lamp, test tube holder, funnel, filter, glasses, stand with test tubes, pipette, graduated cylinder on 10 ml.

I. Organizational moment.

Today in class:

1) You will strengthen the ability to predict the chemical properties of unfamiliar organic substances based on knowledge of functional groups.

2) You will find out what functional groups you know are included in the most famous antipyretic drug.

3) You will find functional groups in a sweet-tasting substance that is used in medicine as a nutrient and component of blood-replacing fluids.

4) You will see how you can get pure silver.

5) We will talk about the physiological effects of ethyl alcohol.

6) We will discuss the consequences of drinking alcoholic beverages by pregnant women.

7) You will be pleasantly surprised: it turns out that you already know so much!

II. Repetition and generalization of students' acquired knowledge.

1. Classification of oxygen-containing organic compounds.

We begin the generalization of the material with the classification of oxygen-containing organic substances. To do this, we will use the table “Classification of oxygen-containing organic compounds”. During frontal work, we will repeat oxygen-containing functional groups.

IN organic chemistry There are three most important functional groups, including oxygen atoms:hydroxyl, carbonyl Andcarboxyl. The latter can be considered as a combination of the previous two. Depending on which atoms or groups of atoms these functional groups are associated with, oxygen-containing substances are divided into alcohols, phenols, aldehydes, ketones and carboxylic acids.

Let's consider these functional groups and their effect on the physical and chemical properties of substances.

Viewing a video clip.

You already know that this is not the only possible classification sign. There can be several identical functional groups in a molecule, and pay attention to the corresponding row of the table.

The next line reflects the classification of substances by the type of radical associated with the functional group. I would like to draw attention to the fact that, unlike alcohols, aldehydes, ketones and carboxylic acids, hydroxyarenes are classified into a separate class of compounds - phenols.

The number of functional groups and the structure of the radical determine the general molecular formula of the substances. In this table they are given only for the limiting representatives of classes with one functional group.

All classes of compounds that “fit” in the table aremonofunctional, i.e., they have only one oxygen-containing function.

To consolidate the material on the classification and nomenclature of oxygen-containing substances, I give several formulas of compounds and ask students to determine “their place” in the given classification and give a name.

formula

Name	Substance class
	Propinic acid	Unsaturated, monobasic acid
	Butanediol-1,4	Limit, dihydric alcohol
	1,3-Dihydroxybenzene	Diatomic phenol
	3-Methylbutanal	Saturated aldehyde
	Butene-3-one-2	Unsaturated ketone
	2-Methylbutanol-2	Limit, monohydric alcohol

Relationship between the structure and properties of oxygen-containing compounds.

The nature of the functional group has a significant impact on the physical properties of substances of this class and largely determines its chemical properties.

The concept of “physical properties” includes the state of aggregation of substances.

Aggregate state of linear connections of different classes:

Number of atoms C in a molecule

Alcohols	Aldehydes	Carboxylic acids
1	and.	G.	and.
2	and.	and.	and.
3	and.	and.	and.
4	and.	and.	and.
5	and.	and.	and.

The homologous series of aldehydes begins with a gaseous substance at room temperature - formaldehyde, and there are no gases among monohydric alcohols and carboxylic acids. What is this connected with?

Molecules of alcohols and acids are additionally connected to each other by hydrogen bonds.

The teacher asks students to formulate the definition of “hydrogen bond”(this is an intermolecular bond between the oxygen of one molecule and the hydroxyl hydrogen of another molecule) , corrects it and, if necessary, dictates for writing: a chemical bond between an electron-deficient hydrogen atom and an electron-rich atom of an element with high electronegativity (F , O , N ) is calledhydrogen.

Now compare the boiling points (°C) of the first five homologs of substances of three classes.

Number of atoms C in a molecule

Alcohols	Aldehydes	Carboxylic acids
1	+64,7	-19	+101
2	+78,3	+21	+118
3	+97,2	+50	+141
4	+117,7	+75	+163
5	+137,8	+120	+186

What can you say after looking at the tables?

In the homologous series of alcohols and carboxylic acids there are no gaseous substances and the boiling points of the substances are high. This is due to the presence of hydrogen bonds between molecules. Due to hydrogen bonds, molecules become associated (as if cross-linked), therefore, in order for the molecules to become free and acquire volatility, it is necessary to expend additional energy to break these bonds.

What can be said about the solubility of alcohols, aldehydes and carboxylic acids in water? (Demonstration of the solubility in water of alcohols - ethyl, propyl, butyl and acids - formic, acetic, propionic, butyric and stearic. A solution of formic aldehyde in water is also demonstrated.)

When answering, the scheme of formation of hydrogen bonds between molecules of acid and water, alcohols, and acids is used.

It should be noted that with increasing molecular weight, the solubility of alcohols and acids in water decreases. The larger the hydrocarbon radical in an alcohol or acid molecule, the more difficult it is for the OH group to keep the molecule in solution due to the formation of weak hydrogen bonds.

3. Genetic relationship between different classes of oxygen-containing compounds.

I draw on the board the formulas of a number of compounds containing one carbon atom:

CH 4 →CH 3 OH → HCOH → HCOOH→ CO 2

Why are they studied in this order in the organic chemistry course?

How does the oxidation state of a carbon atom change?

Students dictate the line: -4, -2, 0, +2, +4

It now becomes clear that each subsequent compound is an increasingly oxidized form of the previous one. From here it is obvious that one should move along the genetic series from left to right using oxidation reactions, and in the opposite direction using reduction processes.

Do ketones fall out of this “circle of relatives”? Of course not. Their predecessors are secondary alcohols.

The chemical properties of each class of substances were discussed in detail in the corresponding lessons. To summarize this material, I proposed assignments on interconversions in a somewhat unusual form as homework.

1. Compound with molecular formulaC 3 H 8 O subjected to dehydrogenation, resulting in a product with the compositionC 3 H 6 O . This substance undergoes a “silver mirror” reaction, forming the compoundC 3 H 6 O 2 . By treating the latter substance with calcium hydroxide, a substance was obtained that is used as a food additive under the code E 282. It prevents the growth of mold in bakery and confectionery products and, in addition, is found in products such as Swiss cheese. Determine the formula of the additive E 282, write the equations for the reactions mentioned and name all the organic substances.

Solution :

CH 3 –CH 2 –CH 2 –OH → CH 3 –CH 2 – COH + H 2 ( cat. – Cu, 200-300 °C)

CH 3 –CH 2 – COH + Ag 2 O → CH 3 –CH 2 – COOH + 2Ag (simplified equation, ammonia solution of silver oxide)

2CH 3 –CH 2 –COOH+WITHa(OH) 2 → (CH 3 –CH 2 – COO) 2 Ca+2H 2 O.

Answer: calcium propionate.

2. Composition compoundC 4 H 8 Cl 2 with a straight carbon skeleton heated with an aqueous solutionNaOH and obtained an organic substance, which, upon oxidationCu(OH) 2 turned intoC 4 H 8 O 2 . Determine the structure of the original compound.

Solution: if 2 chlorine atoms are located at different carbon atoms, then when treated with alkali we would get a dihydric alcohol that would not oxidizeCu(OH) 2 . If 2 chlorine atoms were located at one carbon atom in the middle of the chain, then when treated with alkali, a ketone would be obtained, which does not oxidizeCu(OH) 2. Then, the desired connection is1,1-dichlorobutane.

CH 3 –CH 2 –CH 2 – CHCl 2 + 2NaOH → CH 3 –CH 2 –CH 2 – COH + 2NaCl + H 2 O

CH 3 –CH 2 –CH 2 – COH + 2Cu(OH) 2 →CH 3 –CH 2 –CH 2 – COOH + Cu 2 O+2H 2 O

3. When 19.2 g of sodium salt of saturated monobasic acid was heated with sodium hydroxide, 21.2 g of sodium carbonate was formed. Name the acid.

Solution:

When heated, decarboxylation occurs:

R-COONa + NaOH → RH + Na 2 CO 3

υ (Na 2 CO 3 ) = 21,2 / 106 = 0,2 mole

υ (R-COONa) = 0.2mole

M(R-COONa) = 19.2 / 0.2 = 96G/ mole

M(R-COOH) =M(R-COONa) –M(Na) + M(H) = 96-23+1= 74G/ mole

In accordance with the general formula for saturated monobasic carboxylic acids, to determine the number of carbon atoms, it is necessary to solve the equation:

12n + 2n + 32= 74

n=3

Answer: propionic acid.

To consolidate knowledge about chemical properties ah oxygen-containing organic substances, let's perform the test.

1 option

The following formulas correspond to saturated monohydric alcohols:
A) CH 2 O
B) C 4 H 10 O
IN) C 2 H 6 O
G) CH 4 O
D) C 2 H 4 O 2

It contains a combination of two principles,
One is in the birth of mirrors.
Of course, not for contemplation,
And for the science of understanding.
...And in the kingdom of the forest she meets,
The little brothers are her friends here,
Their hearts are given to them completely...

options:
A) picric acid
B) formic acid
B) acetic acid
D) carboxyl group
D) benzoic acid

Ethanol reacts with substances:
A) NaOH
B) Na
IN) HCl
G) CH 3 COOH
D) FeCl 3

A qualitative reaction to phenols is a reaction with
A) NaOH
B) Cu(OH) 2
IN) CuO
G) FeCl 3
D) HNO 3

Ethanal reacts with substances
A) methanol
B) hydrogen
B) ammonia solution of silver oxide
D) copper (II) hydroxide
D) hydrogen chloride

Option 2

Aldehydes can be obtained
A) oxidation of alkenes
B) oxidation of alcohols
B) hydration of alkynes
D) when heating calcium salts of carboxylic acids
D) hydration of alkenes

The functional group of alcohols is
A) COH
B) OH
IN) COOH
G) N.H. 2
D) NO 2

2-methylbutanol-2
A) unsaturated alcohol
B) limiting alcohol
B) monohydric alcohol
D) tertiary alcohol
D) aldehyde

Did you observe the reaction?
A) for polyhydric alcohols
B) alcohol oxidation
B) interaction of phenol with iron (III) chloride
D) “silver mirror”
D) “copper mirror”

Acetic acid reacts with substances
A) hydrogen
B) chlorine
B) propanol
D) sodium hydroxide
D) metanalem

Students fill out their answers in the table:

1, 2 var.

A	b	V	G	d
1		+	+	+
2		+
3		+	+	+
4				+
5		+	+	+

If you connect the correct answers with a solid line, you get the number “5”.

Group work of students.

Assignment for group 1

Goals:

Reagents and equipment: acetylsalicylic acid (aspirin), water, iron(III) chloride; mortar and pestle, glass rod, alcohol lamp, test tube holder, funnel, filter, glasses, rack with test tubes, pipette, 10 ml graduated cylinder.

Experiment 1. Evidence of the absence of phenolic hydroxyl in acetylsalicylic acid (aspirin).

Place 2-3 grains of acetylsalicylic acid into a test tube, add 1 ml of water and shake vigorously. Add 1-2 drops of iron(III) chloride solution to the resulting solution. What are you observing? Draw conclusions.

No purple color appears. Therefore, in acetylsalicylic acidNOOS-S 6 N 4 -O-CO-CH 3 there is no free phenolic group, since this substance is an ester formed by acetic and salicylic acids.

Experiment 2. Hydrolysis of acetylsalicylic acid.

A crushed acetylsalicylic acid tablet is placed in a test tube and 10 ml of water is added. Bring the contents of the test tube to a boil and boil for 0.5-1 minutes. Filter the solution. Then 1-2 drops of iron(III) chloride solution are added to the resulting filtrate. What are you observing? Draw conclusions.

Write down the reaction equation:

Complete the work by filling out a table that contains the following columns: operation performed, reagent, observations, conclusion.

A purple color appears, indicating the release of salicylic acid containing a free phenolic group. As an ester, acetylsalicylic acid is easily hydrolyzed when boiled with water.

Assignment for group 2

1. Consider the structural formulas of substances, name the functional groups.

2. Do lab work"Detection of functional groups in the glucose molecule".

Goals: consolidate students' knowledge of qualitative reactions of organic compounds, develop skills in experimental determination of functional groups.

Reagents and equipment: solution glucose, universal indicator, copper (II) sulfate solution, sodium hydroxide solution, alcohol lamp, test tube holder, matches, 10 ml graduated cylinder.

2.1. Pour 2 ml of glucose solution into a test tube. Using a universal indicator, draw a conclusion about the presence or absence of a carboxyl group.

2.2. Prepare copper (II) hydroxide: pour 1 ml of copper (II) sulfate into a test tube and add sodium hydroxide to it. Add 1 ml of glucose to the resulting precipitate and shake. What are you observing? What functional groups is this reaction typical for?

2.3. Heat the mixture obtained in experiment No. 2. Note the changes. What functional group is this reaction typical for?

2.4. Complete the work by filling out a table that contains the following columns: operation performed, reagent, observations, conclusion.

Demonstration experience. Interaction of glucose solution with ammonia solution of silver oxide.

Work results:

- there is no carboxyl group, because the solution has a neutral reaction to the indicator;

- the precipitate of copper (II) hydroxide dissolves and a bright blue color appears, characteristic of polyhydric alcohols;

- when this solution is heated, a yellow precipitate of copper (I) hydroxide precipitates, which turns red upon further heating, indicating the presence of an aldehyde group.

Conclusion. Thus, the glucose molecule contains carbonyl and several hydroxyl groups and is an aldehyde alcohol.

Assignment for group 3

Physiological effect of ethanol

1. What is the effect of ethanol on living organisms?

2. Using the equipment and reagents available on the table, demonstrate the effect of ethanol on living organisms. Comment on what you see.

Purpose of the experience: convince students that alcohol denatures proteins and irreversibly disrupts their structure and properties.

Equipment and reagents: rack with test tubes, pipette, 10 ml graduated cylinder, egg white, ethanol, water.

Progress of the experiment: Pour 2 ml of egg white into 2 test tubes. Add 8 ml of water to one, and the same amount of ethanol to the other.

In the first test tube, the protein dissolves and is well absorbed by the body. In the second test tube, a dense white precipitate forms - proteins do not dissolve in alcohol, alcohol takes away water from proteins. As a result, the structure and properties of the protein and its functions are disrupted.

3. Tell us about the effect of ethyl alcohol on various human organs and organ systems.

Explain the consequences of drinking alcohol to pregnant women.

Student performances.

Since ancient times, man has known a large number of toxic substances, all of which differ in the strength of their effect on the body. Among them stands out a substance that is known in medicine as a strong protoplasmic poison - ethyl alcohol. The mortality rate from alcoholism exceeds the number of deaths caused by all infectious diseases combined.

Burning the mucous membrane of the mouth, pharynx, and esophagus, it enters the gastrointestinal tract. Unlike many other substances, alcohol is quickly and completely absorbed in the stomach. Easily crossing biological membranes, after about an hour it reaches its maximum concentration in the blood.

Alcohol molecules quickly penetrate biological membranes into the blood compared to water molecules. Ethyl alcohol molecules can easily cross biological membranes due to their small size, weak polarization, the formation of hydrogen bonds with water molecules, and the good solubility of alcohol in fats.

Quickly absorbed into the blood and dissolving well in the intercellular fluid, alcohol enters all cells of the body. Scientists have found that, by disrupting the functions of cells, it causes their death: when drinking 100 g of beer, about 3000 brain cells die, 100 g of wine - 500, 100 g of vodka - 7500, contact of red blood cells with alcohol molecules leads to the coagulation of blood cells.

The liver neutralizes toxic substances that enter the blood. Doctors call this organ a target for alcohol, since 90% of ethanol is neutralized in it. Chemical processes of ethyl alcohol oxidation occur in the liver.

We recall with students the stages of the alcohol oxidation process:

Ethyl alcohol is oxidized to final decomposition products only if the daily consumption of ethanol does not exceed 20 g. If the dose is exceeded, then intermediate decomposition products accumulate in the body.

This leads to a number of negative side effects: increased formation of fat and its accumulation in liver cells; accumulation of peroxide compounds that can destroy cell membranes, as a result of which the contents of the cells flow out through the formed pores; very undesirable phenomena, the combination of which leads to liver destruction - cirrhosis.

Acetaldehyde is 30 times more toxic than ethyl alcohol. In addition, as a result of various biochemical reactions in tissues and organs, including the brain, the formation of tetrahydropapaveroline is possible, the structure and properties of which resemble well-known psychotropic drugs - morphine and cannabinol. Doctors have proven that it is acetaldehyde that causes mutations and various deformities in embryos.

Acetic acid enhances the synthesis of fatty acids and leads to fatty degeneration of the liver.

While studying the physical properties of alcohols, we addressed the issue of changes in their toxicity in the homologous series of monohydric alcohols. As the molecular weight of substance molecules increases, their narcotic properties increase. If we compare ethyl and pentyl alcohols, the molecular weight of the latter is 2 times greater, and its toxicity is 20 times greater. Alcohols containing three to five carbon atoms form so-called fusel oils, the presence of which in alcoholic beverages increases their toxic properties.

In this series, the exception is methanol - the strongest poison. When 1-2 teaspoons enter the body, the optic nerve is affected, which leads to complete blindness, and consumption of 30-100 ml leads to death. The danger is enhanced due to the similarity of methyl alcohol with ethyl alcohol in properties, appearance, smell.

Together with the students, we try to find the cause of this phenomenon. They put forward various hypotheses. We dwell on the fact that the factors that increase the toxicity of methyl alcohol include the small size of the molecules (high speed of distribution), as well as the fact that the intermediate products of its oxidation - formic aldehyde and formic acid - are strong poisons.

Alcohol that is not neutralized by the liver and the toxic products of its breakdown re-enter the bloodstream and are distributed throughout the body, remaining in it for a long time. For example, alcohol is found unchanged in the brain 20 days after taking it.

We draw students' attention to how alcohol and its breakdown products are eliminated from the body.

C 2 H 5 OH

	10% unchanged via lungs, kidneys and skin
		90% in the form CO 2 And N 2 ABOUT through the lungs and kidneys

Unfortunately, in lately Alcohol consumption, like smoking, is common among women. The influence of alcohol on offspring goes in two directions.

Firstly, alcohol consumption is accompanied by profound changes in the sexual sphere of both men and women. Alcohol and its decomposition products can affect both female and male reproductive cells even before fertilization - their genetic information changes (see Fig. “Healthy (1) and pathological (2) sperm”).

If alcohol consumption is prolonged, the activity of the reproductive system is disrupted, it begins to produce defective germ cells.

Secondly, alcohol directly affects the embryo. Constant consumption of 75-80 g of vodka, cognac or 120-150 g of weaker alcoholic drinks (beer) can cause fetal alcohol syndrome. Through the placenta, not only alcohol, but also its decomposition products, in particular acetaldehyde, which is ten times more dangerous than alcohol itself, enters the waters surrounding the fetus.

Alcohol intoxication has a detrimental effect on the fetus, because its liver, where blood from the placenta first of all enters, does not yet have a special enzyme that decomposes alcohol, and it, not neutralized, spreads throughout the body and causes irreversible changes. Alcohol is especially dangerous in the 7-11th week of pregnancy, when internal organs begin to develop. It negatively affects their development, causing disturbances and changes. The brain is especially affected. Due to the effects of alcohol, dementia, epilepsy, neuroses, heart and kidney disorders can develop, and damage to the external and internal genital organs can occur.

Sometimes damage to the psyche and intellect is observed already in early childhood, but most often they are identified when children begin to study. Such a child is intellectually weakened and aggressive. Alcohol has a much stronger effect on a child's body than on an adult's body. The child’s nervous system and brain are especially sensitive and vulnerable.

So, let’s look at the table “The influence of alcohol on the heredity and health of children” and draw conclusions .

Children's destinies

In families of drinking parents	In families of non-drinking parents
Died in the first months of life	44%	8%
Turned out to be inferior, sick	39%	10%
Healthy physically and mentally	17%	82%

Long-term consumption of alcoholic beverages leads to softening of the cortex. Numerous pinpoint hemorrhages are observed; the transmission of excitation from one nerve cell to another is disrupted. Do not forget the laconic warning words of V.V. Mayakovsky:

Don't drink alcohol.

For those who drink it is poison, for those around it it is torture.

Thus, you have consolidated the ability to predict the chemical properties of unfamiliar organic substances, relying on knowledge of functional groups, repeated the physical and chemical properties of oxygen-containing organic substances, and consolidated the ability to determine the belonging of organic compounds to classes of substances.

III. Homework.

1. Carry out transformations:

2. Explore possible reasons pollution environment near production: methanol, phenol, formaldehyde, acetic acid. Analyze the influence of these substances on natural objects: the atmosphere, water sources, soil, plants, animals and humans. Describe first aid measures for poisoning

Lesson topic:

“Representatives of unsaturated carboxylic acids. Relationship between hydrocarbons, alcohols, aldehydes and acids"

Objective of the lesson: Systematize and deepen students’ knowledge about functional groups and homology using the example of saturated monobasic carboxylic acids. To consolidate students' skills in designating the distribution of electron density in molecules of specific carboxylic acids. Highlight the common chemical properties of acids in inorganic and organic chemistry. Emphasize the unity of substances. Developing the skills to independently apply knowledge when considering unsaturated carboxylic acids. When identifying a genetic connection, show the diversity of organic substances, the transition from a simpler structure to a more complex one, the transition of quantitative changes to qualitative ones, the formation of a dialectical-materialistic worldview.

Equipment: Films for overhead projectors.

1. Model of molecules HCOOH, CH 3 COOH.

2. “Hydrogen bond”

3. “Comparison of acids HCOOH and CH 3 COOH, CH 3 COOH and CH 2 ClCOOH"

4. “Spatial isomers of unsaturated acid C 17 H 33 COOH"

Solutions: CH 3 COOH, Na 2 C0 3 ; NaOH; phenolphthalein; stearic acid C17H35COOH, oleic acid C 17 N 33 COOH, crystalline salt sodium acetate - CH 3 COONa, soap, aspirin, acetate fiber, film, (CH3COO) 2 Pb, latex.

Lesson methods: Conversation, frontal individual survey, use of cards, overhead projector films, demonstration of visuals, conducting experiments.

Lesson plan:

1. Generalization of knowledge about carboxylic acids.

2. Physical properties, occurrence of saturated monobasic carboxylic acids in nature.

3. Chemical properties of saturated monobasic carboxylic acids.

4. Preparation of saturated monobasic carboxylic acids.

5. The use of formic acid, acetic acid and higher limiting monobasic acids.

6. Introduction to unsaturated carboxylic acids, their properties, application.

7. Genetic relationship between hydrocarbons, alcohols, aldehydes, carboxylic acids.

Lesson progress: (introductory word)

Today we continue the conversation about carboxylic acids, substances so diverse in their structure. The areas of their application are interesting and multifaceted.

We only need to introduce a radical multiple bond, and we will become acquainted with unsaturated monobasic carboxylic acids. So, the goal of our lesson is to consolidate and improve knowledge about acids, oxidation products of hydrocarbons, alcohols, aldehydes, independently, using all the accumulated knowledge and ability to predict the properties of unsaturated acids.

I call 6 students to the board to work using cards.

No. 1. "Chemical properties of carboxylic acids"

No. 2. “Special properties of carboxylic acids”

No. 3. "Specific properties of formic acid"

No. 4. "Methods of obtaining formic acid"

No. 5. "Methods for producing acetic acid"

No. 6. “Preparation of stearic acid in the laboratory and according to the method of N.M. Emanuel"

At the same time I am conducting a frontal survey.

Questions for the class:

1. What compounds are called carboxylic acids?

2. How are carboxylic acids classified?

3. Name general formula saturated monobasic carboxylic acids? Name the representatives of the homologous series, give them names?

4. Finding acids in nature (I show the formulas of lactic, citric, oxalic acids).

Let me add: even acids are found in nature in the form of animal and vegetable fats, in oils, and also in wax (i.e. in the form of esters). These acids were discovered a long time ago. Peanut butter contains arachidic acid C 19 N 39 COOH, in palm - palmitic C 15 H 31 COOH.

But odd acids with a large number of carbon atoms are usually not found in nature; they are obtained synthetically and are called Greek numerals.

5. Physical properties of carboxylic acids?

We listen to the answers of the students who worked at the board using cards. After they explained the chemical properties of carboxylic acids, attention was focused on the commonality of organic acids and the peculiarities in the manifestation of properties in organic acids - as substances of a more complex structure.

We carry out experiments typical for inorganic and organic acids. (Experiments were carried out by students on a demonstration table).

1) 2CH3COOH + Mg → (CH 3 COO) 2 Mg + H 2

2H + Mg° → Mg + H2°

2) CH 3 COOH + NaOH → CH 3 COONa + H 2 O

H + OH = H 2 0

3) 2CH3 COOH + Na 2 C0 3 → 2CH 3 COONa + C0 2 + H 2 O

2H + CO 3 → C0 2 + H 2 O.

(showing crystalline salt CH 3 COONa)

After all the students answer at the blackboard, I suggest looking at the model of the molecules HCOOH and CH 3 COOH (projecting film No. 1 through an overhead projector). Questions for the class:

• Where is formic acid used?

We are listening to additional information about the use of the UNNC.

What explains the increase in formic acid production in recent years?

My addition:

Disinfectants and “calming” (distracting) agents are the so-called formic alcohol. This is not just a solution of formic acid in ethanol, its strength is sufficient to catalyze its own own reaction with alcohol - esterification, which acetic acid, for example, is incapable of without the help of another, more powerful one, i.e. we have an equilibrium composition of formic acid, ethanol and ethyl formate.

Formic acid is used to produce solvents. The catalytic activity of HCOOH also plays a role in the production of natural rubber; it is used to coagulate latex. Formic acid cannot be used when tanning leather; here it serves as a catalyst for the hydrolysis of fats contaminating the hide and promotes tanning.

Another important advantage of formic acid: over time, it decomposes by itself, which means the environmental friendliness of any production associated with it. Formic acid can be used for pickling sheet steel, wood processing, the yield of wood pulp would increase by one and a half times, and the problems of environmental pollution, inevitable with the traditional version of the technology that consumes mineral acids, could be largely eliminated.

Where is acetic acid used?

What are herbicides?

Write the structural formulas of some hybridicides. (additional message).

Where are higher carboxylic acids used?

I'm designing film No. 2.

We consider where: (in alcohols, aldehydes, acids), a hydrogen bond is formed.

I'm designing film No. 3.

Let's figure out which acid is stronger:

NCOOH and CH with COOH

CH 3 COOH and CH 3 C1COOH.

Let's consider unsaturated carboxylic acids. I call the student to the board. We write down a chain in which we get acquainted with two unsaturated acids:

CH 3 -CH 2 -COOH → CH 2 =CH-COOH → CH 2 = C - COOH

acrylic ‌‌ │

СНз

metal acrylic acid

Another student:

H 2

C I7 H 35 COOH → C 17 H 33 COOH

oleic acid

Are there spatial isomers for: CH h -(CH 2) 7 -CH=CH-(CH 2) 7 -COOH?

I show film No. 4.

Oleic acid is a cis isomer and its molecular shape is as follows. That the interaction forces between molecules are relatively small, and the substance turns out to be liquid. The molecules of the trans isomer are more elongated; they can be more closely adjacent to each other, the interaction forces between them are large and the substance turns out to be solid - this is ethanedionic acid.

CH 3 -(CH 2) 4 -CH = CH-CH 2 -CH = CH-(CH 2) 7 -COOH

Linoleic acid

What reactions are characteristic of unsaturated acids?

a) Students independently characterize chemical properties. Taking notes:

How acid reacts with alcohols:

CH 2 = C-COOH + NOCH 3 ↔ CH 2 = C - COOCH 3

│ │

CH 3 CH 3

b) How unsaturated compounds are characterized by reactions of addition, polymerization, and oxidation. For example:

C 17 H 35 COOH + H 2 → C 17 H 35 COOH

Oleic stearic

By oxidation of acids, drying oils are obtained from linseed and hemp oil, which contain oleic and linoleic acids in the form of esters.

Let's consider the genetic relationship between carbons and oxygen-containing organic compounds.

I'm designing film No. 5.

I set tasks for groups of students.

Task No. 1. The country in which you live is rich in coal, create a chain to obtain CH h COOH.

The correct answer is:

C + H 2 O + H 2 O + O 2

CaO → CaC 2 → C 2 H 2 → CH 3 SON → CH 3 COOH

Task No. 2. From oil, obtain CH3COOH.

Correct answer:

Oil → pyrolysis → C 2 H 4 → C 2 H 5 OH → CH 3 COOH or

Oil → C 4 H 10 → CH 3 COOH.

Moving from one substance to another, to a more complex structure, we confirm one of the laws of the dialectic of transition to quality; the unity and interconnection of inorganic and organic substances is again traced.

I evaluate students.

Homework.

Tsepkova E.I.,

chemistry teacher

MAOU "SSOSH No. 2"

chemistry

10th grade

UMK.Chemistry.10th grade Textbook for general education organizations: basic

level/G.E.Rudzitiis, F.G.Feldman - 2nd edition - M.: Education, 2012.

The level of training is basic.

Lesson topic:Genetic relationship of saturated monohydric alcohols with hydrocarbons.

Total quantity hours allocated for studying the topic: 6 hours.

Lesson location - 4th lesson on topic

Lesson type: lesson of generalization of knowledge.

Lesson objectives: consolidate, generalize and systematize knowledge on oxygen-containing organic compounds, including on the basis of genetic connections between classes of these substances.

Tasks:

educational: repeat basic terms and concepts on the topic, consolidate knowledge about the composition, structure and properties of alcohols;

developing: the ability to analyze, compare, establish connections between the structure and properties of compounds, develop students’ creative abilities and cognitive interest in chemistry;

educational: pay special attention to the things we use in life.

Methods: verbal, visual, problem-search, knowledge control.

Equipment: computer, screen, projector, table “Classification of oxygen-containing organic substances”, supporting summary “Functional group determines the properties of a substance.”

Planned learning outcomes

Subject. Know the relationship between the composition, structure and properties of substances. Be able to give examples and draw up equations of chemical reactions that reveal

genetic connections between alcohols and hydrocarbons. Practice the ability to make calculations using chemical equations if one of the reactants is taken in excess.

Metasubject. Be able to organize educational cooperation and joint activities with the teacher and peers, work individually and in a group (find general solution and resolve conflicts based on coordination of positions and taking into account interests), formulate, argue and defend their opinions.

Personal. To form a holistic worldview that corresponds to the modern level of development of science, based on ideas about the genetic connection between different

classes of organic substances. Develop communication competence.

Progress of the lesson.

I. Organizational moment.

II. Guys, today in the lesson we will solve genetic problems, on which we will consolidate the knowledge gained during the study of topics.

The properties of hydrocarbons depend on the chemical, spatial, electronic structure of molecules and the nature of chemical bonds.

Study of the structure, chemical properties and methods of producing hydrocarbons various groups shows that they are all genetically related among themselves, i.e. transformation of some hydrocarbons into others is possible:

This allows for targeted synthesis of specified compounds using a series of necessary chemical reactions (chain of transformations).

Task 1. Name the intermediate products in the transformation scheme:

Ethyl alcohol H 2 SO 4 (k), t X HBr Y Na Z Cr 2 O 3 Al 2 O 3 butadiene-1,3

Solution. In this chain of transformations, including 4 reactions, from ethyl alcohol WITH 2 N 5 HE butadiene-1,3 must be obtained CH 2 =CH–CH=CH 2 .
1. When heating alcohols with concentrated sulfuric acid
H 2 SO 4 (water-removing agent) occurs dehydration with the formation of an alkene. The elimination of water from ethyl alcohol leads to the formation of ethylene:

2. Ethylene is a representative of alkenes. Being an unsaturated compound, it is capable of undergoing addition reactions. As a result hydrobromination ethylene:

3.When bromoethane is heated in the presence of sodium metal ( Wurtz reaction, n-butane is formed (substance Z):

4.Dehydrogenation n-butane in the presence of a catalyst is one of the methods for producing butadiene-1,3 CH 2 =CH–CH=CH 2
(Section 5.4. Preparation of alkadienes).

Answer:


1. Carry out transformations:

Performing exercises to consolidate knowledge.

Students complete assignments in their workbooks.

Using the genetic connection diagram, indicate from which substances, the formulas of which are given in the task, alcohols can be obtained in one stage? Write down the equations for the corresponding reactions. Name the starting materials and products of the reaction. For suffixes in the names of hydrocarbons and halogenated hydrocarbons, underline the multiplicity of the bond accordingly.

Name the class of substances and establish a genetic relationship (show this with arrows).

Carry out transformations:

CaC 2 → A → B → H 3 C-CH 2 -Cl → B → H 3 C-CH 2 -O-C 3 H 7

CaC 2 + 2H 2 O → HC≡CH + Ca(OH) 2 A

2) HC≡CH + 2H 2 → H 3 C-CH 3 B

3) H 3 C-CH 3 + C1 2 → H 3 C-CH 2 -C1 + HC1

4) H 3 C-CH 2 -C1 + KOH (aq.) → H 3 C-CH 2 -OH + KS1 B

5) H 3 C-CH 2 -OH + HO-C 3 H 7 → H 3 C-CH 2 -O-C 3 H 7 + H 2 O

Now let's complicate our task a little. . Make a chain of transformations from proposed connections. Among the formulas of substances there are “extra” ones. How does this task compare to the previous one?

a )C 6H5- OH, b) C 4H8, c) C 6H5- Br, d) C 5H11-Cl, e) C 6H6, f) C 3H6, g )HC≡CH, h)H 2 C =CH 2 i) CH 4 .

CH 4 → HC≡CH → C 6 H 6 → C 6 H 5 -Br → C 6 H 5 -OH

2CH 4 → HC≡CH + 3H 2

3HC≡CH → C 6 H 6

3. C 6 H 6 + Br 2 → C 6 H 5 Br + HBr

4. C 6 H 5 -Br + KOH → C 6 H 5 -OH + KBr

Reinforcing the properties of hydrocarbons in the form of a game “No-yes”»
1. Can you get alcohol from ethene? (Yes)
2. Is ethanol found in plant leaves? (No)
3. Fermentation of sugary substances produces methanol? (No)
4. Can ethanol be produced from wood chips by fermentation? (No)
5. If you freeze potatoes, can you get ethyl alcohol? (Yes)

.Reflective test:
1. This will be useful to me in life.
2. There was a lot to think about during the lesson.
3. I received answers to all the questions I had.
4. I worked conscientiously during the lesson.

Homework. Pov.§20-21, transformation schemes exercises 14,15*,

Carry out the transformations:
C2H5OH-C2H5CL-C2H5OH-C2H5OC2H5
CO2
References

Chemistry.Organic chemistry.10th grade: textbook. for general education institutions: basic level G.E. Rudzitis, F.G. Feldman. – 13th ed.-M.: Education, 2009.

Chemistry 8-11 grade ( thematic planning based on the textbook by G.E. Rudzitis, F.G. Feldman) / comp. Breiger L.M.-Volgograd: Teacher-AST, 1999

Chemistry. Large reference book for preparing for the Unified State Exam: educational methodological manual/ Edited by V.N. Doronkina. - 2nd edition, revised - Rostov n/D: Legion, 2016.

Surovtseva R.P. and others. Chemistry. 10-11 grades: Methodological manual. - M.: Bustard, 2000.