Comparative table of oxygen-containing organic compounds.

Phenols

Phenols called derivatives of aromatic hydrocarbons, the molecules of which contain one or more hydroxyl groups directly connected to the benzene ring.

The simplest representative of this class C 6 H 5 OH is phenol.

The structure of phenol. One of the two unshared electron pairs of the oxygen atom is drawn into the -electron system of the benzene ring. This leads to two effects: a) the electron density in the benzene ring increases, and the electron density maxima are in ortho - and pair- positions in relation to the OH group;

b) the electron density on the oxygen atom, on the contrary, decreases, which leads to a weakening O-N connections. The first effect is manifested in the high activity of phenol in electrophilic substitution reactions, and the second - in the increased acidity of phenol compared to saturated alcohols.

Monosubstituted phenol derivatives, such as methylphenol (cresol), can exist as three structural isomers ortho - , meta - , para - cresols:

OH OH OH

about– cresol m– cresol P– cresol

Receipt. Phenols and cresols are found in coal tar and also in petroleum. In addition, they are formed during the cracking of oil.

AT industry phenol is obtained:

1) from halobenzenes. When chlorobenzene and sodium hydroxide are heated under pressure, sodium phenolate is obtained, with further processing which acid forms phenol: C 6 H 5 Cl + 2NaOH → C 6 H 5 ONa + NaCl + H 2 O;

C 6 H 5 Cl + H 2 SO 4 → C 6 H 5 OH + NaHSO 4;

2) when catalytic oxidation of isopropylbenzene (cumene) atmospheric oxygen to form phenol and acetone.

CH 3 —CH—CH 3 OH

О 2 + CH 3 —C—CH 3 .

This is the main industrial way obtaining phenol.

3) phenol is obtained from aromatic sulfonic acids. The reaction is carried out by fusing sulfonic acids with alkalis. Initially formed phenoxides are treated with strong acids to obtain free phenols.

SO 3 H ONa

3NaOH → + Na 2 SO 3 + 2H 2 O.

sodium phenoxide

Physical properties. The simplest phenols are viscous liquids or low-melting solids with characteristic carbolic smell. Phenol is soluble in water (especially in hot water), other phenols are slightly soluble. Most phenols are colorless substances, but darken when stored in air due to oxidation products.

Chemical properties .

1. Acidity phenol is higher than that of saturated alcohols; it reacts like with alkali metals

2C 6 H 5 OH + 2Na → 2C 6 H 5 ONa + H 2,

and with their hydroxides:

C 6 H 5 OH + NaOH → C 6 H 5 ONa + H 2 O.

Phenol, however, is a very weak acid. When passing carbon dioxide or sulfur dioxide through a solution of phenolates, phenol is released. This proves that phenol is a weaker acid than carbonic or sulphurous.

C 6 H 5 ONa + CO 2 + H 2 O → C 6 H 5 OH + NaHCO 3.

2. Esters formation. They are formed by the action of carboxylic acid chlorides on phenol (and not the acids themselves, as in the case of alcohols). O

C 6 H 5 OH + CH 3 COCl → C 6 H 5 -C -CH 3 + HCl.

phenylacetate

3. Ether formation occurs when phenol reacts with haloalkanes.

C 6 H 5 OH + C 2 H 5 Cl → C 6 H 5 -O - C 2 H 5.

phenylethyl ether

5. Electrophilic substitution reactions with phenol flow much easier than with aromatic hydrocarbons. Since the OH group is a type I orientant, the reactivity of the benzene ring in the phenol molecule increases ortho- and pair- provisions.

a) bromination. Under the action of bromine water on phenol, three hydrogen atoms are replaced by bromine and a precipitate of 2, 4, 6 - tribromophenol is formed: OH

OH Br Br

3Br 2 → + 3HBr.

This is a qualitative reaction to phenol.

b) nitration. IS HE

IS HE

This video tutorial was created specifically for self-study topic "Oxygen-containing organic substances". In this lesson, you will learn about a new kind of organic matter containing carbon, hydrogen and oxygen. The teacher will talk about the properties and composition of oxygen-containing organic substances.

Topic: Organic matter

Lesson: Oxygen-Containing Organic Substances

1. The concept of a functional group

The properties of oxygen-containing organic substances are very diverse, and they are determined by which group of atoms the oxygen atom belongs to. This group is called functional.

A group of atoms that essentially determines the properties of an organic substance is called a functional group.

There are several different oxygen-containing groups.

Hydrocarbon derivatives, in which one or more hydrogen atoms are replaced by a functional group, belong to a certain class of organic substances (Table 1).

Tab. 1. The belonging of a substance to a certain class is determined by the functional group

2. Alcohols

Monohydric saturated alcohols

Consider individual representatives and general properties of alcohols.

The simplest representative of this class of organic substances is methanol, or methyl alcohol. Its formula is CH3OH. It is a colorless liquid with a characteristic alcohol odor, highly soluble in water. methanol- this is very poisonous substance. A few drops, taken orally, lead to blindness of a person, and a little more of it - to death! Previously, methanol was isolated from wood pyrolysis products, so its old name, wood alcohol, has been preserved. Methyl alcohol is widely used in industry. It is made from medications, acetic acid, formaldehyde. It is also used as a solvent for varnishes and paints.

No less common is the second representative of the class of alcohols - ethyl alcohol, or ethanol. Its formula is C2H5OH. By their own physical properties ethanol is practically no different from methanol. Ethyl alcohol is widely used in medicine, it is also part of alcoholic beverages. Ethanol is obtained in organic synthesis sufficient a large number of organic compounds.

Getting ethanol. The main way to obtain ethanol is the hydration of ethylene. The reaction takes place at high temperature and pressure, in the presence of a catalyst.

CH2=CH2 + H2O → C2H5OH

The reaction of interaction of substances with water is called hydration.

Polyhydric alcohols

Polyhydric alcohols include organic compounds, the molecules of which contain several hydroxyl groups connected to a hydrocarbon radical.

One of the representatives of polyhydric alcohols is glycerol (1,2,3-propanetriol). The composition of the glycerol molecule includes three hydroxyl groups, each of which is located at its own carbon atom. Glycerin is a very hygroscopic substance. It is able to absorb moisture from the air. Due to this property, glycerin is widely used in cosmetology and medicine. Glycerin has all the properties of alcohols. The representative of two atomic alcohols is ethylene glycol. Its formula can be viewed as the formula of ethane, in which the hydrogen atoms at each atom are replaced by hydroxyl groups. Ethylene glycol is a syrupy liquid with a sweetish taste. But it is very poisonous, and in no case should it be tasted! Ethylene glycol is used as antifreeze. One of common properties alcohols is their interaction with active metals. As part of the hydroxyl group, the hydrogen atom can be replaced by an active metal atom.

2C2H5OH + 2Na→ 2С2Н5ОNa+ H2 &

Target: to form the ability to make observations and draw conclusions, write down the equations of the corresponding reactions in molecular and ionic forms .

Security of the lesson

1. Collection guidelines for students to complete practical exercises and laboratory work on the discipline "Chemistry".

2. Sodium hydroxide solution, sodium carbonate, calcium carbonate, copper (II) oxide, acetic acid, litmus blue, zinc; stand with test tubes, water bath, heating device, matches, test tube holder.

Theoretical material

Carboxylic acids are organic compounds whose molecules contain one or more carboxyl groups connected to a hydrocarbon radical or a hydrogen atom.

Obtaining: In the laboratory, carboxylic acids can be obtained from their salts by treating them with sulfuric acid when heated, for example:

2CH 3 - COOHa + H 2 SO 4 ® 2CH 3 - COOH + Na 2 SO 4
In industry, it is obtained by oxidation of hydrocarbons, alcohols and aldehydes.

Chemical properties:
1. Due to the shift in electron density from the hydroxyl group O–H to strongly

polarized carbonyl group C=O, carboxylic acid molecules are capable of

electrolytic dissociation: R–COOH → R–COO - + H +

2.Carboxylic acids have properties characteristic of mineral acids. They react with active metals, basic oxides, bases, salts of weak acids. 2CH 3 COOH + Mg → (CH 3 COO) 2 Mg + H 2

2CH 3 COOH + CaO → (CH 3 COO) 2 Ca + H 2 O

H–COOH + NaOH → H–COONa + H2O

2CH 3 CH 2 COOH + Na 2 CO 3 → 2CH 3 CH 2 COONa + H 2 O + CO 2

CH 3 CH 2 COOH + NaHCO 3 → CH 3 CH 2 COONa + H 2 O + CO 2

Carboxylic acids are weaker than many strong mineral acids

CH 3 COONa + H 2 SO 4 (conc.) →CH 3 COOH + NaHSO 4

3. Formation of functional derivatives:

a) when interacting with alcohols (in the presence of concentrated H 2 SO 4), they form esters.

The formation of esters by the interaction of an acid and an alcohol in the presence of mineral acids is called an esterification reaction. CH 3 - -OH + HO-CH 3 D CH 3 - -OCH 3 + H 2 O

acetic acid methyl methyl ester

acetic acid alcohol

The general formula of esters is R– –OR’ where R and R" are hydrocarbon radicals: in formic acid esters – formates –R=H.

The reverse reaction is the hydrolysis (saponification) of the ester:

CH 3 – –OCH 3 + HO–H DCH 3 – –OH + CH 3 OH.

Glycerin (1,2,3-trihydroxypropane; 1,2,3-propanetriol) (glycos - sweet) chemical compound with the formula HOCH2CH(OH)-CH2OH or C3H5(OH)3. The simplest representative of trihydric alcohols. It is a viscous transparent liquid.

Glycerin is a colorless, viscous, hygroscopic liquid, infinitely soluble in water. Sweet taste (glycos - sweet). It dissolves many substances well.

Glycerol is esterified with carboxylic and mineral acids.

Esters of glycerol and higher carboxylic acids are fats.

Fats - these are mixtures of esters formed by the trihydric alcohol glycerol and higher fatty acids. The general formula of fats, where R are the radicals of higher fatty acids:

Most often, fats include saturated acids: palmitic C15H31COOH and stearic C17H35COOH, and unsaturated acids: oleic C17H33COOH and linoleic C17H31COOH.

Common name compounds of carboxylic acids with glycerol - triglycerides.

b) when exposed to water-removing reagents as a result of intermolecular

dehydration anhydrides are formed

CH 3 – –OH + HO– –CH 3 →CH 3 – –O– –CH 3 + H 2 O

Halogenation. Under the action of halogens (in the presence of red phosphorus), α-halo-substituted acids are formed:

Application: in food and chemical industry(production of cellulose acetate, from which acetate fiber, organic glass, film are obtained; for the synthesis of dyes, medicines and esters).

Questions to consolidate the theoretical material

1 Which organic compounds are carboxylic acids?

2 Why are there no gaseous substances among carboxylic acids?

3 What causes the acidic properties of carboxylic acids?

4 Why does the color of indicators change in acetic acid solution?

5 What chemical properties are common for glucose and glycerol, and how do these substances differ from each other? Write the equations for the corresponding reactions.

Exercise

1. Repeat theoretical material on the topic of the practice.

2. Answer questions to consolidate the theoretical material.

3. Investigate the properties of oxygen-containing organic compounds.

4. Prepare a report.

Execution instructions

1. Familiarize yourself with the safety rules for working in a chemical laboratory and sign in the safety journal.

2. Perform experiments.

3. Enter the results in the table.

Experience No. 1 Testing a solution of acetic acid with litmus

Dilute the resulting acetic acid with a little water and add a few drops of blue litmus or dip an indicator paper into the test tube.

Experience No. 2 Reaction of acetic acid with calcium carbonate

Pour a little chalk (calcium carbonate) into a test tube and add a solution of acetic acid.

Experience No. 3 Properties of glucose and sucrose

a) Add 5 drops of glucose solution, a drop of copper (II) salt solution and, while shaking, a few drops of sodium hydroxide solution into a test tube until a light blue solution is formed. This experiment was done with glycerol.

b) Heat the resulting solutions. What are you watching?

Experience No. 4 Qualitative reaction for starch

To 5-6 drops of starch paste in a test tube, add a drop alcohol solution iodine.

Sample report

Laboratory work№ 9 Chemical properties of oxygen-containing organic compounds.

Purpose: to form the ability to make observations and draw conclusions, write down the equations of the corresponding reactions in molecular and ionic forms .

Make a conclusion in accordance with the purpose of the work

Literature 0-2 s 94-98

Lab #10

This video tutorial was created specifically for self-study of the topic "Oxygen-containing organic substances". During this lesson, you will learn about a new type of organic matter containing carbon, hydrogen and oxygen. The teacher will talk about the properties and composition of oxygen-containing organic substances.

Topic: Organic matter

Lesson: Oxygen-Containing Organic Substances

The properties of oxygen-containing organic substances are very diverse, and they are determined by which group of atoms the oxygen atom belongs to. This group is called functional.

A group of atoms that essentially determines the properties of an organic substance is called a functional group.

There are several different oxygen-containing groups.

Hydrocarbon derivatives, in which one or more hydrogen atoms are replaced by a functional group, belong to a certain class of organic substances (Table 1).

Tab. 1. The belonging of a substance to a certain class is determined by the functional group

Monohydric saturated alcohols

Consider individual representatives and general properties of alcohols.

The simplest representative of this class of organic substances is methanol, or methyl alcohol. Its formula is CH 3 OH. It is a colorless liquid with a characteristic alcohol odor, highly soluble in water. methanol- this is very poisonous substance. A few drops, taken orally, lead to blindness of a person, and a little more of it - to death! Previously, methanol was isolated from wood pyrolysis products, so its old name has been preserved - wood alcohol. Methyl alcohol is widely used in industry. Medicines, acetic acid, formaldehyde are made from it. It is also used as a solvent for varnishes and paints.

No less common is the second representative of the class of alcohols - ethyl alcohol, or ethanol. Its formula is C 2 H 5 OH. In terms of its physical properties, ethanol is practically no different from methanol. Ethyl alcohol is widely used in medicine, it is also part of alcoholic beverages. A sufficiently large amount of organic compounds is obtained from ethanol in organic synthesis.

Getting ethanol. The main way to obtain ethanol is the hydration of ethylene. The reaction takes place at high temperature and pressure, in the presence of a catalyst.

CH 2 \u003d CH 2 + H 2 O → C 2 H 5 OH

The reaction of interaction of substances with water is called hydration.

Polyhydric alcohols

Polyhydric alcohols include organic compounds, the molecules of which contain several hydroxyl groups connected to a hydrocarbon radical.

One of the representatives of polyhydric alcohols is glycerol (1,2,3-propanetriol). The composition of the glycerol molecule includes three hydroxyl groups, each of which is located at its own carbon atom. Glycerin is a very hygroscopic substance. It is able to absorb moisture from the air. Due to this property, glycerin is widely used in cosmetology and medicine. Glycerin has all the properties of alcohols. The representative of two atomic alcohols is ethylene glycol. Its formula can be viewed as the formula of ethane, in which the hydrogen atoms at each atom are replaced by hydroxyl groups. Ethylene glycol is a syrupy liquid with a sweetish taste. But it is very poisonous, and in no case should it be tasted! Ethylene glycol is used as antifreeze. One of the common properties of alcohols is their interaction with active metals. As part of the hydroxyl group, the hydrogen atom can be replaced by an active metal atom.

2C 2 H 5 OH + 2Na→ 2C 2 H 5 ONa+ H 2

Sodium ethylate is obtained, and hydrogen is released. Sodium ethylate is a salt-like compound that belongs to the class of alcoholates. By virtue of their weaknesses acid properties alcohols do not interact with alkali solutions.

Carbonyl compounds

Rice. 2. Individual representatives of carbonyl compounds

The carbonyl compounds are aldehydes and ketones. Carbonyl compounds contain a carbonyl group (see Table 1). the simplest aldehyde is formaldehyde. Formaldehyde is a gas with a pungent odor extremely poisonous! A solution of formaldehyde in water is called formalin and is used to preserve biological preparations (see Figure 2).

Formaldehyde is widely used in industry to make plastics that do not soften when heated.

The simplest representative ketones is an acetone. It is a liquid that dissolves well in water and is mainly used as a solvent. Acetone has a very strong odor.

carboxylic acids

The composition of carboxylic acids contains a carboxyl group (see Fig. 1). The simplest representative of this class is methane, or formic acid. Formic acid is found in ants, nettles and spruce needles. Nettle burn is the result of the irritant action of formic acid.

Tab. 2.

Of greatest importance is acetic acid. It is necessary for the synthesis of dyes, medicines (for example, aspirin), esters, acetate fibers. 3-9% aqueous solution of acetic acid - vinegar, flavoring and preservative.

In addition to formic and acetic carboxylic acids, there are a number of natural carboxylic acids. These include citric and lactic, oxalic acids. Lemon acid found in lemon juice, raspberries, gooseberries, rowan berries, etc. Widely used in Food Industry and medicine. Citric and lactic acids are used as preservatives. Lactic acid is produced by the fermentation of glucose. Oxalic acid used to remove rust and as a dye. The formulas of individual representatives of carboxylic acids are given in Tab. 2.

Higher fatty carboxylic acids usually contain 15 or more carbon atoms. For example, stearic acid contains 18 carbon atoms. Salts of higher carboxylic acids sodium and potassium are called soaps. sodium stearate S 17 H 35 SOONais part of the solid soap.

There is a genetic link between the classes of oxygen-containing organic substances.

Summing up the lesson

You learned that the properties of oxygen-containing organic substances depend on which functional group is included in their molecules. The functional group determines whether a substance belongs to a certain class of organic compounds. There is a genetic link between the oxygen-containing classes of organic substances.

1. Rudzitis G.E. Inorganic and organic chemistry. Grade 9: Textbook for educational institutions: basic level / G.E. Rudzitis, F.G. Feldman. - M.: Education, 2009.

2. Popel P.P. Chemistry. Grade 9: Textbook for general education educational institutions/ P.P. Popel, L.S. Krivlya. - K .: Information Center "Academy", 2009. - 248 p.: ill.

3. Gabrielyan O.S. Chemistry. Grade 9: Textbook. - M.: Bustard, 2001. - 224 p.

1. Rudzitis G.E. Inorganic and organic chemistry. Grade 9: Textbook for educational institutions: basic level / G.E. Rudzitis, F.G. Feldman. - M.: Enlightenment, 2009. - Nos. 2-4, 5 (p. 173).

2. Give the formulas of two homologues of ethanol and the general formula of the homologous series of saturated monohydric alcohols.

The material considers the classification of oxygen-containing organic substances. Questions of homology, isomerism and nomenclature of substances are analyzed. The presentation is full of tasks on these issues. Consolidation of the material is offered in a test exercise for compliance.

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Lesson objectives: to get acquainted with the classification of oxygen-containing organic compounds; construction of homologous series of substances; detection possible types isomerism; construction of structural formulas of isomers of substances, nomenclature of substances.

Classification of substances C x H y O z carboxylic acids aldehydes ketones esters alcohols phenols monoatomic - many R - OH R - (OH) n simple complex OH \u003d R - C - O OH \u003d R - C - O H - oic acid -al R-C-R || O-one R - O - R \u003d R - C - O O - R - ol - n ol

Homologous series CH 3 - OH C 2 H 5 - OH C 3 H 7 - OH C 4 H 9 - OH C 5 H 11 - OH methanol ethanol propanol-1 butanol-1 pentanol-1 Alcohols C n H 2n+2O

Carboxylic acids \u003d H - C - O OH \u003d CH 3 - C - O OH \u003d CH 3 - CH 2 - C - O OH methane acid (formic) ethanoic acid (acetic) propanoic acid (propionic) C n H 2n O2

Aldehydes = H - C - O H \u003d CH 3 - C - O H \u003d CH 3 - CH 2 - C - O H

Ketones CH 3 - C - CH 3 || O CH 3 - CH 2 - C - CH 3 || O CH 3 - CH 2 - CH 2 - C - CH 3 || O propane he (acetone) butane he pentane he-2 C n H 2n O

Ethers CH 3 - O -CH 3 C 2 H 5 - O -CH 3 C 2 H 5 - O -C 2 H 5 C 3 H 7 - O -C 2 H 5 C 3 H 7 - O -C 3 H 7 dimethyl ether methethyl ether diethyl ether ethyl propyl ether dipropyl ether C n H 2n + 2 O Conclusion: ethers are derivatives of saturated monohydric alcohols.

Esters \u003d H - C - O O - CH 3 \u003d CH 3 - C - O O - CH 3 \u003d CH 3 - CH 2 - C - O O - CH 3 formic acid methyl ester (methyl formate) acetic acid methyl ester (methyl acetate ) propionic acid methyl ester C n H 2n O 2 Conclusion: esters are derivatives of carboxylic acids and alcohols.

alcohols esters ketones aldehydes carboxylic acids isomerism and nomenclature of carbon skeleton isomerism interclass (esters) carbon skeleton interclass (ketones) carbon skeleton f-group position (-C=O) interclass (aldehydes) carbon skeleton f-group position (-OH) interclass (ethers) carbon skeleton interclass

Drawing up formulas of isomers. Nomenclature of substances. Task: compose structural formulas possible isomers for substances of composition C 4 H 10 O; C 4 H 8 O 2; C 4 H 8 O. What classes do they belong to? Name all substances according to the systematic nomenclature. C 4 H 10 O C 4 H 8 O 2 C 4 H 8 O C n H 2n + 2 O C n H 2n O 2 C n H 2n O alcohols and ethers carboxylic acids and esters aldehydes and ketones

CH 3 - CH 2 - CH - CH 3 | OH CH 3 | CH 3 - C - CH 3 | OH CH 3 - O - CH 2 - CH 2 - CH 3 CH 3 - CH 2 - O - CH 2 - CH 3 butanol-1 2-methylpropanol-1 butanol-2 2-methylpropanol-2 methyl propyl ether diethyl ether I alcohols II alcohol III alcohol

CH 3 - CH 2 - CH 2 - C - O OH \u003d CH 3 - CH - C - O OH | CH3 \u003d CH 3 - CH 2 - C - O O - CH 3 \u003d CH 3 - C - O O - CH 2 - CH 3 butanoic acid 2-methylpropanoic acid methyl propionic acid ethyl ester of acetic acid

CH 3 - CH 2 - CH 2 - C - O H \u003d CH 3 - CH - C - O H | CH3 CH 3 - CH 2 - C - CH 3 || O butanal 2-methylpropanal butanone-2

Check yourself! 1. Match: general formula class substance R – COOH R – O – R R – COH R – OH R – COOR 1 R – C – R || O sl. esters alcohols carb. to-you ketones aldehydes etc. esters a) C 5 H 11 -OH b) C 6 H 13 -SON c) C 4 H 9 -O - CH 3 d) C 5 H 11 -COOH e) CH 3 -CO - CH 3 f) CH 3 -COOS 2 H 5 2. Name the substances according to the systematic nomenclature.

Check yourself! I II III IV V VI 3 6 5 2 1 4 D C B A E D

Homework Paragraph (17-21) - parts 1 and 2 of ex. 1,2,4,5 pp. 153-154 2 pp. 174 The lesson is over!