Monobasic saturated carboxylic acids. Polyhydric saturated alcohols
The tests were compiled by: chemistry teacher of KSU “Secondary School No. 5” Kalinicheva E. A.
Petropavlovsk, Republic of Kazakhstan
Grade 11. Control test option 1
1. Not a hydrocarbon:
A) CH 4 B) C 2 H 4 C) C 3 H 8 D) C 6 H 14 E) C 2 H 5 OH
C) peptide bond
D) benzene ring
A) chemical structure B) qualitative and quantitative composition C) color
D) the general formula of the homologous series E) the number of carbon and hydrogen atoms
4. Substances whose formulas CH 3 – CH 2 – OH and CH 3 – O – CH 3 are:
A) Homologues B) Isomers C) Alcohols
D) Esters E) Ketones
A) 32% B) 42% C) 52% D) 62% E) 72%
6. The sum of all coefficients in the reaction equation for the interaction of ethanol with sodium:
A) 2 B) 4 C) 6 D) 7 E) 5
7. A reaction that is unusual for monohydric alcohols:
D) silver mirror E) dehydration
8. The volume of hydrogen (at standard conditions) that is formed by the interaction of 4.6 g of sodium metal with ethanol:
A) 2.24 l B) 11.2 l C) 1.12 l D) 22.4 l E) 6.72 l
9. When glycerol reacts with copper (II) hydroxide, the following is formed:
A) Copper glycerate (II) B) Copper C) Copper oxide (I) D) Propanol E) Copper oxide (II)
10. Glycerin is not used to obtain:
A) ointments B) nitroglycerin C) dynamite
D) giving tissues softness and elasticity E) ethanol
11. The oxidation of aldehydes produces:
A) Carboxylic acids B) Alcohols C) Phenols
E) Esters E) Fats
12. The amount of ethyl acetate obtained from 32 g of ethanol and 30 g of acetic acid:
A) 0.5 mol B) 0.55 mol C) 0.1 mol D) 0.6 mol E) 0.4 mol
13. Monosaccharides include:
A) sucrose B) maltose C) starch
D) cellulose E) glucose
14. During alcoholic fermentation of 200 g of 9% glucose solution, carbon dioxide is formed in volume (at standard conditions):
A) 22.4 l B) 8.96 l C) 4.48 l
D) 2.24 l E) 3.36 l
15. Lactic acid fermentation does not occur when:
A) Fermentation of berries B) Compacted silage of feed
C) Pickling cucumbers D) Souring milk
E) Pickling cabbage
Grade 11. . Control test option 2
A) functional hydroxyl group
B) functional carboxyl group
C) peptide bond
D) benzene ring
E) functional carbonyl group
5. Mass of salt that is formed by the interaction of 0.25 mol of acetic acid with 20 g of calcium metal:
A) 16.75 g B) 17.75 g C) 19.75 g D) 20.75 g E) 18.75 g
6. Product of the reaction of propanal with an ammonia solution of silver oxide (I):
A) Propanol B) Propanediol C) Propanic acid
D) Propyl acetate E) Methylpropyl ether
7. The mass of acetic acid obtained from 330 g of acetaldehyde with a 70% yield of the reaction product is:
A) 450 g B) 405 g C) 360 g D) 270 g E) 315 g
8. The composition of soap is expressed by the formula:
A) CH 3 COONa B) C 3 H 7 COONa C) C 4 H 9 COONa D) C 2 H 5 COONa E) C 17 H 35 COONa
9. From 71 g of stearic acid, soap was obtained containing 75% sodium stearate, weighing:
10. According to the structure of glucose:
A) polyhydric alcohol and aldehyde B) aldehyde and acid C) phenol and aldehyde
E) dihydric alcohol and aromatic hydrocarbon E) alcohol and ketone
A) AgOH B) AgNO 3 C) 2Ag D) Cu 2 O E) CuO
12. The sum of all coefficients in the equation for the reaction of alcoholic fermentation of glucose:
A) 2 B) 4 C) 6 D) 7 E) 5
13. β – glucose is a monomer:
A) Maltose B) Sucrose C) Cellulose
D) Starch E) Glycogen
14. When cellulose reacts with nitric acid, the following is formed:
D) disaccharide E) monosaccharide
15. In nature, cellulose is formed as a result of:
A) Oxidation B) Photosynthesis C) Hydrolysis
D) Fermentation E) Isomerization
Grade 11. Oxygen-containing organic substances. Control test option 3
1. A substance with the general formula R - C - O – R 1 belongs to the class:
D) acids E) esters
2. The reaction between an alcohol and an acid is called:
A) hydrolysis B) hydrogenation C) esterification
D) hydration E) addition
3. The volume of hydrogen (at standard conditions) that is formed by the interaction of 0.6 mol of acetic acid with 0.5 mol of sodium metal:
A) 22.4 l B) 44.8 l C) 11.2 l D) 5.6 l E) 89.6 l
4. Animal fats are hard because they contain...
B) only mineral acids
5. One of the products of alkaline hydrolysis of fats:
A) organic ethers B) ethyl alcohol C) bases
D) mineral acids E) soap
6. To obtain 1 kg of soap, which contains sodium stearate with a mass fraction of 61.2%, you need stearic acid with a mass of:
A) 603 g B) 928 g C) 370 g D) 1136 g E) 568 g
7. Disaccharides include:
D) Glucose E) Fructose
8. Molecular formula of sucrose:
9. Isn't physical property sucrose substances:
A) Without color B) Hard C) Sweet
D) Insoluble in water E) Odorless
10. Subject to hydrolysis:
A) Glucose B) Galactose C) Fructose D) Sucrose E) Ribose
11. Isomers differ from each other:
A) chemical structure B) qualitative and quantitative composition C) color D) general formula of the homologous series E) number of carbon and hydrogen atoms
12. Glucose isomer:
A) Cellulose B) Sucrose C) Ribose D) Fructose E) Starch
13. In production, glucose is most often obtained:
A) By hydrolysis of cellulose B) By hydrolysis of insulin C) As a result of photosynthesis
D) Hydrolysis of starch E) From formaldehyde in the presence of calcium hydroxide
14. Mass fraction of carbon in glucose:
A) 30% B) 40% C) 50% D) 60% E) 70%
15. From 1620 kg of potatoes containing 20% starch, you can get glucose in the following mass (yield 75%):
Grade 11. Oxygen-containing organic substances. Control test option 4
1. Ethylene glycol C 2 H 4 (OH) 2 is:
A) the closest homolog of glycerol B) the simplest hydrocarbon
C) saturated monohydric alcohol D) dihydric alcohol
E) the simplest phenol
2. Mass fraction of carbon in ethylene glycol:
A) 39% B) 45% C) 52% D) 64% E) 73%
3. To recognize glycerol use:
A) Ag 2 O (ammonia solution) B) Cu (OH) 2 C) Br 2 (bromine water)
E) C 2 H 5 OH E) HCl
4. Aldehyde molecules contain:
A) functional hydroxyl group
B) functional carboxyl group
E ) carbonyl functional group
A) Neutralization B) Oxidation C) Hydration
D) Esterification E) Saponification
6. The sum of all coefficients in the Kucherov reaction equation:
A) 3 B) 4 C) 2 D) 5 E) 6
7. If the yield is 85%, then the mass of acetaldehyde, which is obtained from 4.48 m 3 of acetylene using the Kucherov reaction:
A) 7.48 kg B) 8.48 kg C) 10.48 kg D) 9.48 kg E) 6.48 kg
8. The “silver mirror” reaction is characteristic of both substances:
A) Sucrose and glycerol B) Glucose and glycerol
C) Glucose and formaldehyde D) Glycerin and formaldehyde
E) Sucrose and formaldehyde
9. According to the structure of glucose:
A) dihydric alcohol and aromatic hydrocarbon B) aldehyde and acid
C) phenol and aldehyde D) alcohol and ketone E) polyhydric alcohol and aldehyde
10. Product of the interaction of the non-cyclic form of glucose with Ag 2 O (ammonia solution):
A) Sorbitol B) Ester C) Gluconic acid
D) Xylitol E) Copper (II) alcoholate
11. When 18 g of glucose is oxidized with an ammonia solution of silver oxide, silver will be released (75% yield) in the following mass:
A) 13.2 g B) 16.2 g C) 15.2 g D) 17.2 g E) 14.2 g
12. Isomers differ from each other:
A) chemical structure B) color C) qualitative and quantitative composition D) general formula of the homologous series E) number of carbon and hydrogen atoms
13. Isomers:
A) Glucose and sucrose B) Fructose and ribose C) Starch and maltose
D) Glucose and fructose E) Cellulose and sucrose
14. The number of hydroxyl groups in an open-chain ribose molecule:
A) 1 B) 2 C) 4 D) 5 E) 3
15. The volume of carbon (IV) (n.s., in l) released during the fermentation of glucose, if ethyl alcohol weighing 460 g was formed:
A) 224 B) 112 C) 22.4 D) 67.2 E) 11.2
Grade 11. Oxygen-containing organic substances. Control test option 5
1. Not a hydrocarbon:
A) CH 4 B ) C 2 H 5 OH C) C 3 H 8 D) C 6 H 14 E) C 2 H 4
2. The molecules of saturated alcohols contain:
A) functional carbonyl group B) functional carboxyl group
C) peptide bond D) benzene ring
E) functional hydroxyl group
3. Isomers differ from each other:
A ) quality C)
4. Isomers are:
5. Mass fraction of carbon in ethanol:
A) 52% B) 42% C) 32% D) 62% E) 72%
6. To recognize ethanol use:
7. Mass fraction of acetaldehyde yield, if the interaction of 92 g of ethanol with copper (II) oxide yields 80 g of aldehyde:
A) 90.9% B) 92.2% C) 93% D) 88.2% E) 92%
8. The sum of all coefficients in the reaction equation for the interaction of ethanol with copper oxide (II):
A) 3 B) 4 C) 2 D) 5 E) 6
9. The reaction between an alcohol and an acid is called:
A) hydrolysis B) hydrogenation C) esterification
D) hydration E) addition
10. Mass of ester (75%) obtained by reacting 2.4 g of methanol with 2.76 g of formic acid:
A) 6.9 g B) 2.7 g C) 6.5 g D) 3.5 g E) 2.1
11. Bee honey consists mainly of a mixture of:
A) Glucoses and fructoses B) Pentoses and hexoses
C) Ribose and deoxyribose D) Starch and glucose
E) Glucose and sucrose
12. Ketone alcohol is:
A) Glucose B) Fructose C) Cellulose
D) Ribose E) Deoxyribose
13. To recognize glucose use:
A) Indicator and alkali solution
B) Bromine water
C) Potassium permanganate
D) Copper oxide
E) Ammonia solution of silver oxide (I)
14. If in the laboratory, during the oxidation of 3.6 g of glucose, 3 g of gluconic acid was obtained, then its yield (%) is:
A) 68.5% B) 76.5% C) 72.5% D) 74.5% E) 70.5%
15. Natural high molecular weight compound:
A) Glucose B) Fiber C) Maltose
D) Sucrose E) Polyethylene
Grade 11. Oxygen-containing organic substances. Control test option 6
1. Aldehyde molecules contain:
A) functional hydroxyl group B) functional carbonyl group C) peptide bond D) functional carboxyl group E) benzene ring
2. Aldehydes include:
A) 1) H 3 C - COOH, 2) H 3 C - COCl B) 1) C 6 H 5 SOS 6 H 5, 2) HOOS - COOH C) 1) H - SON, 2) C 2 H 5 - SON D) 1) C 6 H 5 OH, 2) C 6 H 5 COOH
E) 1) H 3 C – CO - CH 3, 2) H 3 C – CH 2 – COBr
3.Qualitative reaction for acetaldehyde - this is interaction with:
A) Cu 2 O B) Br 2 C) HCl D) Ag 2 O E) C 2 H 5 OH
4. Mass fraction of carbon in acetaldehyde:
A) 52% B) 55% C) 32% D) 65% E) 48%
5. Reactions characteristic of aldehydes:
A) Neutralization B) Saponification C) Hydration
D) Esterification E) Addition
6. Unsaturated carboxylic acid:
D) Stearic E) Capronic acid
7. Bromine water in oleic acid becomes discolored because:
A) the molecule contains a carboxyl group
B) the molecule has spatial isomerism
WITH ) oleic acid – unsaturated acid
D) contained in solid fats
E) is a heavy carboxylic acid
8. Animal fats are hard because they contain...
A) unsaturated carboxylic and mineral acids
B) only mineral acids
C) saturated and unsaturated carboxylic acids
D) unsaturated carboxylic acids
E) saturated carboxylic acids
9. To obtain 1 kg of soap containing 76.5% sodium stearate, you need stearic acid weighing:
A) 710 g B) 570 g C) 750 g D) 780 g E) 645 g
10. A natural polymer is:
A) starch B) polypropylene C) fructose
D) sucrose E) polyethylene
11. To recognize starch use:
A ) J 2 (solution) B) Br 2 (solution) C) KMnO 4 (solution) D) C u (OH) 2 E) Ag 2 O (ammonia solution)
12. By hydrolysis of 1620 g of starch, glucose was obtained (yield 75%). The mass of ethanol formed during the fermentation of this glucose:
A) 630 g B) 720 g C) 700 g D) 690 g E) 650 g
13. The sum of all coefficients in the equation for the reaction of alcoholic fermentation of glucose:
A) 5 B) 4 C) 6 D) 7 E) 2
14. The occurrence of the “silver mirror” reaction in glucose causes:
A) amino group B) ketone group C) carboxyl group
D) aldehyde group E) nitro group
15. The hydrolysis of cellulose produces:
A) Fructose B) Glucose C) Ribose and glucose
D) Ribose C) Fructose and glucose
Grade 11. Oxygen-containing organic substances. Control test option 7
1. Carboxylic acid molecules contain:
A) functional carboxyl group B) functional hydroxyl group
C) peptide bond D) benzene ring
E) functional carbonyl group
2. A chemical reaction that is unusual for carboxylic acids:
A) 2CH 3 COOH + 2Ag → 2CH 3 COOAg + H 2
B) 2CH 3 COOH + Ca → (CH 3 COO) 2 Ca + H 2
C) CH 3 COOH + C 2 H 5 OH → CH 3 COOC 2 H 5 + H 2 O
E) CH 3 COOH + Na OH → CH 3 COONa + H 2 O
E) 2CH 3 COOH + Na 2 CO 3 → 2CH 3 COONa + H 2 O + CO 2
3. Mass fraction of carbon in acetic acid:
A) 60% B) 50% C) 30% D) 40% E) 70%
4. The reaction between an alcohol and an acid is called:
A) hydrolysis B) hydrogenation C) hydration
D) esterification E) addition
5. The sum of the coefficients in the equation for the reaction of acetic acid with potassium hydroxide:
A) 2 B) 4 C) 3 D) 5 E) 6
6. The mass of ethyl acetic acid obtained by reacting 180 g of acetic acid with 200 g of ethyl alcohol is:
A) 264 g B) 88 g C) 220 g D) 132 g E) 176 g
7. Glycerol, acetaldehyde, acetic acid and glucose can be recognized using one reagent:
A) Ag 2 O B) FeCl 3 C) Br 2 E) NaOH E) Cu(OH) 2
8. Polysaccharides include:
A) glucose B) fructose C) cellulose D) ribose E) sucrose
9. Acetate fiber is obtained by esterification:
A) Cellulose with nitric acid B) Cellulose with sulfuric acid
C) Glucose with acetic anhydride
D) Cellulose with acetic anhydride
E) Starch with acetic anhydride
10. When cellulose reacts with nitric acid, the following is formed:
A) ether B) ester C) nitro compound
D) disaccharide E) monosaccharide
11. Glucose is formed in the reaction: H + Ca(OH) 2
12. Mass of ethanol, which is formed during alcoholic fermentation of 18 g of glucose, if the yield is 70%:
A) 3.44 g B) 6.44 g C) 15.44 g D) 12.44 g E) 9.44 g
13. Isomers:
A) Glucose and sucrose B) Fructose and ribose C) Starch and ribose
E) Cellulose and sucrose E) Starch and cellulose
14. Determine the yield of glucose if it is known that 135 g of glucose is obtained from 1 ton of potatoes containing 16.2% starch:
A) 45% B) 65% C) 75% D) 82% E) 37.5%
15. Glucose is not used:
A) For making marmalade B) For making soap
C) To obtain gluconic acid D) As a valuable nutritional product
E) As a strengthening remedy
Grade 11. Oxygen-containing organic substances. Control test option 8
1. Polyhydric alcohols include:
A) ethanol B) phenol C) glycerin D) benzene E) toluene
2. A substance that is not used to produce glucose:
A) maltose B) starch C) sucrose D) sorbitol E) glycerol
3. Mass fraction of carbon in glucose:
A) 40% B) 55% C) 35% D) 50% E) 60%
4. Mass of glucose required to obtain 575 ml of ethanol (p = 0.8 g/ml):
A) 1800 g B) 450 g C) 900 g D) 1000 g E) 225 g
5. Disaccharides include:
A) Starch B) Cellulose C) Sucrose
D) Glucose E) Fructose
6. Molecular formula of sucrose:
A) C 5 H 10 O 5 B) C 5 H 10 O 4 C) C 6 H 12 O 6 D) C 12 H 22 O 11 E) C 2 H 2 O 2
7. This is not a physical property of the substance sucrose:
A) Insoluble in water B) Solid C) Sweet
D) No color E) No smell
8. The presence of several hydroxyl groups in sucrose is determined by:
A) calcium hydroxide B) sodium chloride
C) silver nitrate
D) copper hydroxide (II)
E) zinc hydroxide
9. When glucose interacts with freshly prepared Cu (OH) 2 without heating, the following is formed: A) Bright blue solution B) Yellow precipitate C) Orange precipitate D) Black precipitate E) Blue precipitate
10. Mass of sugar required to prepare 300 g of 10% solution:
A) 45 g B) 3 g C) 15 g D) 30 g E) 60 g
11. Pentoses include:
A) Fructose B) Lactose C) Starch
D) Maltose E) Deoxyribose
12. Deoxyribose contains functional groups:
A) 4 hydroxyl groups and 1 aldehyde group
B) 5 hydroxyl groups and 1 aldehyde group
WITH) 3 hydroxyl groups and 1 aldehyde group
E) 4 hydroxyl groups and 1 carboxyl group
E) 4 hydroxyl groups and 1 ketone group
13. When 1 g of glucose is completely broken down, energy is released:
A) 17.6 kJ B) 13.5 kJ C) 16.7 kJ D) 15.5 kJ E) 20.4 kJ
14. A substance with the general formula R - C - O – R 1 belongs to the class:
A) alcohols B) aldehydes C) ethers
D) acids E) esters
15. Mass of ether, which is formed by the interaction of 150 g of a 12% acetic acid solution with 110 g of a 40% ethanol solution:
A) 23.8 g B) 26.4 g C) 25.8 g D) 27.5 g E) 24.7 g
Grade 11 . Oxygen-containing organic substances. Control test option 9
1. A class of organic compounds that contains the functional group ∕ O in the molecule is called: A) phenols B) amines
C C) carboxylic acids D) aldehydes
H E) monohydric alcohols
2. Relative molecular weight of acetaldehyde:
A) 30 B) 44 C) 56 D) 65 E) 72
3. Relative hydrogen density of methanal:
A) 15 B) 11 C) 10 D) 12 E) 14
4. The oxidation of aldehydes produces:
A) Fats B) Alcohols C) Phenols
E) Esters E) Carboxylic acids
5. The sum of all coefficients in the Kucherov reaction equation:
A) 5 B) 4 C) 2 D) 3 E) 6
6. If the yield is 85%, then the mass of acetaldehyde, which is obtained from 4.48 m 3 of acetylene using the Kucherov reaction:
A) 6.48 kg B) 8.48 kg C) 10.48 kg D) 9.48 kg E) 7.48 kg
7. Isomers differ from each other:
A) qualitative quantitative composition B) color C) chemical structure D) general formula of the homologous series E) number of carbon and hydrogen atoms
8. Isomers of carboxylic acids are:
A) saturated monohydric alcohols B) esters C) aldehydes
D) polyhydric alcohols E) fats
9. Chemical reaction that is unusual for carboxylic acids:
A) 2CH 3 COOH + Ca → (CH 3 COO) 2 Ca + H 2
B) 2CH 3 COOH + 2Ag → 2CH 3 COOAg + H 2
C) CH 3 COOH + C 2 H 5 OH → CH 3 COOC 2 H 5 + H 2 O
E) CH 3 COOH + Na OH → CH 3 COONa + H 2 O
E) 2CH 3 COOH + Na 2 CO 3 → 2CH 3 COONa + H 2 O + CO 2
10. The reaction between an alcohol and an acid is called:
A) hydrolysis B) hydrogenation C) esterification
D) hydration E) addition
11. When 23 g of ethanol reacts with sodium, hydrogen is released in the amount of substance:
A) 0.8 mol B) 0.25 mol C) 0.6 mol D) 0.1 mol E) 0.4 mol
12. Not a physical property of ethanol:
A) Highly soluble in water B) Colorless C) Solid
D) Has an alcoholic smell E) Narcotic substance
13. To recognize ethanol use:
A) Ag 2 O (ammonia solution) B) Cu (OH) 2 C) CuO
E) Br 2 (bromine water) E) HCl
14. One of the products of fat hydrolysis:
A) ethyl alcohol B) mineral acids C) Soap
D) organic ethers E) bases
15. Mass laundry soap, containing 50% sodium stearate, obtained from 284 g of stearic acid:
A) 568 g B) 612 g C) 284 g D) 153 g E) 306 g
Grade 11. Oxygen-containing organic substances. Control test option 10
1. Not a hydrocarbon:
A) CH 4 B) C 2 H 4 C) C 2 H 5 OH D) C 6 H 14 E) C 3 H 8
2. The molecules of saturated alcohols contain:
A) functional hydroxyl group
B) functional carboxyl group
C) peptide bond
D) benzene ring
E) functional carbonyl group
3. Mass fraction of carbon in ethanol:
A) 62% B) 42% C) 32% D) 52% E) 72%
4. The sum of all coefficients in the reaction equation for the interaction of ethanol with sodium:
A) 2 B) 7 C) 6 D) 4 E) 5
5. A reaction that is unusual for monohydric alcohols:
A) combustion B) oxidation C) esterification
D) dehydration E) silver mirror
6. In the transformation scheme
C 2 H 4 → C 2 H 5 Br → C 2 H 5 OH → C 2 H 5 – O - C 2 H 5 stage and the mass of alcohol required to obtain 7.4 g of ether are:
A) 2 and 9.2 g B) 2 and 8.7 g C) 3 and 9.2 g D) 1 and 8.9 g E) 1 and 4.6 g
7. Isomers are:
A) alcohols and acids B) alcohols and ethers C) esters and aldehydes D) aldehydes and alcohols E) acids and salts
8. Mosaccharides include:
A) Starch B) Cellulose C) Sucrose
D) Glucose E) Lactose
9. Glucose is formed in the reaction: H + Ca(OH) 2
A) C 2 H 5 ОNa + CH 3 J → B) (C 6 H 10 O 5 )n + nH 2 O → C) 6 НСО →
E) CH 3 –CH 2 -OH + CH 3 -COOH → E) C 36 H 74 +5O 2 →
10. As a result of fermentation, glucose forms the substance C 3 H 6 O 3. It's called:
A) acetic acid B) propyl alcohol C) lactic acid
D) gluconic acid E) ethyl alcohol
11. When the non-cyclic form of glucose reacts with an ammonia solution of silver oxide, the product is formed:
A) AgOH B) AgNO 3 C) 2Ag D) Cu 2 O E) CuO
12. From 1620 kg of potatoes containing 20% starch, you can get glucose in the following mass (yield 75%):
A) 300 g B) 360 g C) 270 g D) 220 g E) 180 g
13. Unsaturated carboxylic acid:
A) Palmitic B) Margarine C) Oleic
D) Stearic E) Capronic acid
14. The composition of soap is expressed by the formula:
A) CH 3 COONa B) C 3 H 7 COONa C) C 4 H 9 COONa D) C 2 H 5 COONa E) C 17 H 35 COONa
15. From 71 g of stearic acid, soap was obtained containing 75% sodium stearate, weighing:
A) 114.8 g B) 57.4 g C) 51 g D) 73 g E) 102 g
Chistyakova A.B., chemistry teacher MBOU secondary school No. 55 Ivanovo city Class 10
TEST ON THE TOPIC “OXYGEN-CONTAINING ORGANIC SUBSTANCES”.
1 option
- General formula of saturated monohydric alcohol:
TEST ON THE TOPIC “OXYGEN-CONTAINING ORGANIC SUBSTANCES” 10 CL.
Option 2
- General formula of saturated carboxylic acids:
Answers:
Literature:
- Gabrielyan O.S., Ostroumov I.G. "Chemistry. Methodical manual 10th grade." M., “Bustard”, 2005 Gorkovenko M.Yu. "Lesson developments in chemistry, grade 10." M. “VAKO, 2008 Koroshchenko A.S. “Knowledge control in organic chemistry 9-11.” M., “Vlados”, 2003 Malykhina Z.V. "Test tasks in organic chemistry for grades 10-11." M., “Creative Center”, 2001 2 Inspection and verification work in organic chemistry. Chemistry 10 A basic level of" M., Bustard, 2010.
The work presents tasks - tests using the following methods:
"Analogies";
search for significant signs;
“Excluding unnecessary things”;
Correspondence;
Multiple Choice
Instructions for tasks:
1. The number of answers to the questions is determined by the number of empty squares.
2. For task No. 2, you need to write down the names of substances according to systematic nomenclature.
3. Task No. 6 has three questions. For each question there is one correct answer.
4. Task No. 12 has three questions. For each question there is one correct answer.
Topic: “Properties of oxygen-containing organic substances” Basic level.
1. Specify the class of organic substances by definition:
Hydrocarbon derivatives, the molecules of which contain several hydroxyl groups bonded to different carbon atoms:
A. aldehydes B. polyhydric alcohols
B. carbohydrates D. ketones
2. Give the names of the substances according to systematic nomenclature:
A. CH3− CH2− OH B. CH3− COOH C. CH3− HC = O D. CH3− C (CH3)2 OH
A___________________
B.___________________
IN. __________________
G. __________________
3. Which of the following characteristics is not essential for monohydric alcohols:
A. the presence of carbon atoms in the molecule B. the presence of one OH group
B. interaction with hot copper D. intermolecular dehydration
wire coated with CuO.
4. What class of oxygen-containing organic substances does the -COOH group belong to?
A. monohydric alcohols
B. polyhydric alcohols
B. carboxylic acids
G. aldehydes
5. Remove an unnecessary name from the list:
Formaldehyde, methanol, propanoic acid, toluene, hexanol, formic acid.
________________
6. In each question, choose one of the four words that makes this statement true:
Glycerin - yes - ?
A. polyhydric alcohol B. harmonium
B. amino acid D. aldehyde
Carbonyl group - is part of - ?
A. electrolyzer B. polyhydric alcohols
V. amines G. aldehyde
Propanic acid - ? - butanoic acid
A. homologues B. isomers
B. polymers D. copolymers
7. Eliminate the unnecessary name from this list:
oleic acid, butyric acid, linoleic acid, linolenic acid, acrolein.
8. Which of the following is an essential characteristic of aldehydes:
A. interaction with an ammonia solution of Ag2O when heated
B. negatively affect nervous system
V. burn in air to form CO2 and H2O
D. presence of oxygen in the molecule
9. Reaction name for the conversion: acetic acid + ethanol ↔ ester + water
A. hydrogenation B. esterification
B. polymerization D. pyrolysis
10. Eliminate two extra substances from the list of reactants with the acid in the reaction scheme:
CH3COOH + B. OH
11. Which of the concepts proposed in the answers is related to the concept of “aldehydes” in a functional relationship?
a) silver mirror b) sp2-hybridization of the carbon atom of the carbonyl group
c) catalyst d) hydrogen bond
12. Choose the correct statement
Benzaldehyde: aromatic aldehyde = Benzoic acid: ?
a) limiting b) highest c) polybasic d) arene e) monobasic
Saturated monohydric alcohols: СnH2n+2O = Aldehydes: ?
a) СnH2n-6 b) СnH2n+1O c) СnH2n d) СnH2nO e) СnH2n-1O.
Ethylene glycol: liquid = ? : gas
a) formalin b) formaldehyde c) formic acid d) acetone e) naphthalene
13. Indicate which substances can be used to prove the presence of phenol:
A. bromine water B. chlorine C. iron (III) chloride solution
G. potassium permanganate (aq.) D. lime water
Tests as a tool for measuring the level of knowledge on the topic: “Oxygen-containing organic compounds with environmental elements”
Introduction
Chapter I. Testing as a form of knowledge control
Chapter II. The state of the issue being studied in modern Russian school
2.1 Monohydric saturated alcohols
2.2 Polyhydric saturated alcohols
2.3 Phenols
2.4 Aldehydes
2.5 Monobasic saturated carboxylic acids
2.6 Esters
Chapter III. Environmental features of studying the topic: “Oxygen-containing organic compounds”
Chapter IV. My lessons
Literature
INTRODUCTION
In the modern era of scientific and technological revolution, issues of interaction between nature and man have acquired extraordinary complexity and importance. The rapid growth of the world's population, the intensive development of technology have many times increased the degree of human impact on nature, the consumption of various natural resources. A serious problem has become the issues of possible and, moreover, rapid depletion of mineral reserves, fresh water, flora and fauna resources, environmental pollution.
Environmental problems are global in nature and affect all of humanity.
Among the most concerning, undoubtedly, are problems associated with environmental pollution: air, soil, water. In order for a chemistry course to acquire an “ecological sound”, it must be recognized that one of its main goals will be the formation in students of a new, responsible attitude towards nature.
CHAPTER 1. TESTING AS ONE OF THE FORMS OF KNOWLEDGE CONTROL
One of the important tasks of qualimetry is the quick and reliable assessment of human knowledge. The theory of pedagogical tests is considered as part of pedagogical qualimetry. The state of control of knowledge of school students using test meters was investigated and the main problems when using tests were identified: the quality and validity of the content of test tasks, the reliability of test results, the shortcomings of processing results according to the classical theory of tests, the lack of use of the modern theory of processing test materials using computer technology. The high measurement error of the test results does not allow us to talk about the high reliability of the measurement results.
Testing is one of the most technologically advanced forms of automated control with controlled quality parameters. In this sense, none of the known forms of monitoring students’ knowledge can compare with testing. But there is no reason to absolutize the capabilities of the test form.
The use of diagnostic tests in foreign schools has a long history. A recognized authority in the field of pedagogical testing, E. Thorndike (1874-1949), identifies three stages in the introduction of testing into the practice of American schools:
1. Search period (1900-1915). At this stage, there was an awareness and initial implementation of tests of memory, attention, perception and others proposed by the French psychologist A. Binet. Intelligence tests are being developed and tested to determine IQ.
2. The next 15 years were the “boom” years in the development of school testing, when many tests were developed and implemented. This led to a final understanding of the role and place of testing, opportunities and limitations.
3. Starts in 1931 modern stage development of school testing. The search for specialists is aimed at increasing the objectivity of tests, creating a continuous (end-to-end) system of school test diagnostics, subordinated to a single idea and general principles, creating new, more advanced means of presenting and processing tests, accumulating and effectively using diagnostic information. Let us recall in this regard that pedology, which developed in Russia at the beginning of the century, unconditionally accepted the test basis of objective school control.
After the well-known resolution of the Central Committee of the All-Union Communist Party of Bolsheviks “On pedological perversions in the system of Narkompros” (1936), not only intellectual, but also harmless academic achievement tests were eliminated. Attempts to revive them in the 70s came to nothing. In this area, our science and practice are significantly behind foreign ones.
In schools in developed countries, the introduction and improvement of tests has proceeded at a rapid pace. Diagnostic tests of school performance have become widespread, using the form of alternatively selecting the correct answer from several plausible ones, writing a very short answer (filling in the blanks), adding letters, numbers, words, parts of formulas, etc. With the help of these simple tasks, it is possible to accumulate significant statistical material, subject it to mathematical processing, and obtain objective conclusions within the limits of those tasks that are presented for testing. Tests are printed in the form of collections, attached to textbooks, and distributed on computer floppy disks.
Types of test knowledge control
When preparing materials for test control, you must adhere to the following basic rules:
You cannot include answers that cannot be justified by students as incorrect at the time of testing. - Incorrect answers should be constructed based on typical errors and should be plausible. - Correct answers among all suggested answers should be placed in random order. - Questions should not repeat the wording of the textbook. - Answers to some questions should not be clues for answers to others. - Questions should not contain “traps”.
Learning tests are used at all stages of the didactic process. With their help, preliminary, current, thematic and final control of knowledge, skills, and recording of progress and academic achievements are effectively ensured.
Learning tests are increasingly penetrating into mass practice. Nowadays, almost all teachers use short-term surveys of all students in each lesson using tests. The advantage of such a check is that the whole class is busy and productive at the same time, and in a few minutes you can get a snapshot of the learning of all students. This forces them to prepare for each lesson, to work systematically, which solves the problem of efficiency and the necessary strength of knowledge. When checking, first of all, gaps in knowledge are identified, which is very important for productive self-learning. Individual and differentiated work with students to prevent academic failure is also based on current testing.
Naturally, not all the necessary characteristics of assimilation can be obtained by testing. For example, indicators such as the ability to specify one’s answer with examples, knowledge of facts, the ability to coherently, logically and demonstrably express one’s thoughts, and some other characteristics of knowledge, skills and abilities cannot be diagnosed by testing. This means that testing must necessarily be combined with other (traditional) forms and methods of verification. Those teachers who, using written tests, give students the opportunity to verbally justify their answers act correctly. Within the framework of classical test theory, the level of knowledge of test takers is assessed using their individual scores, converted into certain derived indicators. This allows us to determine the relative position of each subject in the normative sample.
The most significant advantages of IRT include measuring the values of parameters of subjects and test items on the same scale, which makes it possible to correlate the level of knowledge of any subject with the degree of difficulty of each test item. Critics of the tests intuitively realized the impossibility of accurately measuring the knowledge of subjects of different levels of training using the same test. This is one of the reasons that in practice they usually strive to create tests designed to measure the knowledge of subjects of the most numerous, average level of preparedness. Naturally, with this orientation of the test, the knowledge of strong and weak subjects was measured with less accuracy.
In foreign countries, control practice often uses so-called success tests, which include several dozen tasks. Naturally, this allows you to more fully cover all the main sections of the course. Submitted tasks are usually completed in writing. Two types of tasks are used:
a) requiring students to independently compose an answer (tasks with a constructive type of answer);
b) tasks with a selective response type. In the latter case, the student chooses from among those presented the answer that he considers correct.
It is important to note that these types of assignments are subject to significant criticism. It is noted that tasks with a constructive type of answer lead to biased assessments. Thus, different examiners and often even the same examiner give different marks for the same answer. In addition, the more freedom students have in answering, the more options there are for evaluating teachers.
CHAPTER 2. STATE OF THE ISSUE STUDYED IN THE MODERN RUSSIAN SCHOOL
Topic study plan
Topic “Alcohols and phenols” (6–7 hours)
1. Alcohols: structure, nomenclature, isomerism. 2. Physical and chemical properties of alcohols. 3. Production and use of methanol and ethanol. 4. Polyhydric alcohols. 5. Phenol: structure and properties. 6. Genetic relationship between hydrocarbons and alcohols.
Topic “Aldehydes and carboxylic acids” (9 hours)
1. Aldehydes: structure and properties.
2. Preparation and use of aldehydes.
3. Saturated monobasic carboxylic acids.
4. Individual representatives of carboxylic acids (formic, palmitic, stearic, oleic acids).
5. Soaps as salts of higher carboxylic acids. Use of acids.
6. Practical work No. 3 “Preparation and properties of carboxylic acids.”
7. Practical work No. 4 “Experimental solution of problems on the recognition of organic compounds.”
Teaching of the topic begins in 10th grade, the first half of the year. When studying this topic, use a chemistry textbook edited by G.E. Rudzitis, F.G. Feldman, also a textbook for grade 10, edited by N.S. Akhmetova. The didactic material is a book on chemistry for 10th grade, edited by A.M. Radetsky, V.P. Gorshkova; assignments are used for independent work in chemistry for grade 10, edited by R.P. Surovtseva, S.V. Sofronova; A collection of problems in chemistry for high school and for those entering universities, edited by G.P., is used. Khomchenko, I.G. Khomchenko.
2.1 Monohydric saturated alcohols Cn N2n+1 OH
Molecular structure
From the electronic formula of alcohol it is clear that in its molecule the chemical bond between the oxygen atom and the hydrogen atom is very polar. Therefore, hydrogen has a partial positive charge, and oxygen has a partial negative charge. And as a consequence: 1) the hydrogen atom bonded to the oxygen atom is mobile and reactive; 2) the formation of hydrogen bonds between individual alcohol molecules and between alcohol and water molecules is possible:
Receipt
In industry:
a) hydration of alkenes:
b) fermentation of sugary substances:
c) by hydrolysis of starch-containing products and cellulose, followed by fermentation of the resulting glucose;
d) methanol is obtained from synthesis gas:
In the laboratory:
a) from halogen derivatives of alkanes, acting on them with AgOH or KOH:
C 4 H 9 Br + AgOH C 4 H 9 OH + AgBr;
b) hydration of alkenes:
Chemical properties
1. Interaction with alkali metals:
2C 2 H 5 – OH + 2Na 2C 2 H 5 – ONa + H 2.
3. Oxidation reactions:
a) alcohols are burning:
2C 3 H 7 OH + 9O 2 6CO 2 + 8H 2 O;
b) in the presence of oxidizing agents, alcohols oxidize:
4. Alcohols are exposed dehydrogenation And dehydration:
2.2 Polyhydric saturated alcohols
Molecular structure
In terms of molecular structure, polyhydric alcohols are similar to monohydric alcohols. The difference is that their molecules contain several hydroxyl groups. The oxygen they contain displaces the electron density from the hydrogen atoms. This leads to an increase in the mobility of hydrogen atoms and an increase in acidic properties.
Receipt
In industry:
a) hydration of ethylene oxide:
b) glycerin is obtained synthetically from propylene and by hydrolysis of fats.
In the laboratory: like monohydric alcohols, by hydrolysis of halogenated alkanes with aqueous solutions of alkalis:
Chemical properties
Polyhydric alcohols have a similar structure to monohydric alcohols. In this regard, their properties are also similar.
1. Interaction with alkali metals:
2. Interaction with acids:
3. Due to the increased acidic properties, polyhydric alcohols, unlike monohydric alcohols, react with bases (with an excess of alkali):
2.3 Phenols
R–OH or R(OH) n
Molecular structure
Unlike alkane radicals (CH 3 –, C 2 H 5 –, etc.), the benzene ring has the property of attracting the electron density of the oxygen atom of the hydroxyl group. As a result, the oxygen atom, stronger than in alcohol molecules, attracts electron density from the hydrogen atom. Therefore, in a phenol molecule, the chemical bond between the oxygen atom and the hydrogen atom becomes more polar, and the hydrogen atom is more mobile and reactive.
Receipt
In industry:
a) isolated from pyrolysis products coal; b) from benzene and propylene:
c) from benzene:
C 6 H 6 C 6 H 5 Cl C 6 H 5 – OH.
Chemical properties
In the phenol molecule, the mutual influence of atoms and atomic groups is most clearly manifested. This is revealed by comparison chemical properties phenol and benzene and the chemical properties of phenol and monohydric alcohols.
1. Properties associated with the presence of the –OH group:
2. Properties associated with the presence of a benzene ring:
3. Polycondensation reactions:
2.4 Aldehydes
Molecular structure
The electronic and structural formulas of aldehydes are as follows:
In aldehydes, in the aldehyde group there is an -bond between the carbon and hydrogen atoms, and between the carbon and oxygen atoms there is one -bond and one -bond, which is easily broken.
Receipt
In industry:
a) oxidation of alkanes:
b) oxidation of alkenes:
c) hydration of alkynes:
d) oxidation of primary alcohols:
(this method is also used in the laboratory).
Chemical properties
1. Due to the presence of - bonds in the aldehyde group, the most characteristic addition reactions:
2. Oxidation reactions(leak easily):
3.Polymerization and polycondensation reactions:
2.5 Monobasic saturated carboxylic acids
Molecular structure
The electronic and structural formulas of monobasic carboxylic acids are as follows:
Due to the shift in electron density towards the oxygen atom in the carbonyl group, the carbon atom acquires a partial positive charge. As a result, carbon attracts electron density from the hydroxyl group, and the hydrogen atom becomes more mobile than in alcohol molecules.
Receipt
In industry:
a) oxidation of alkanes:
b) oxidation of alcohols:
c) oxidation of aldehydes:
d) specific methods:
Chemical properties
1. The simplest carboxylic acids dissociate in an aqueous solution:
CH 3 COOH H + + CH 3 COO – .
2. React with metals:
2HCOOH + Mg (HCOO) 2 Mg + H 2 .
3. React with basic oxides and hydroxides:
HCOOH + KOH HCOOC + H 2 O.
4. React with salts of weaker and volatile acids:
2CH 3 COOH + K 2 CO 3 2CH 3 COOC + CO 2 + H 2 O.
5. Some acids form anhydrides:
6. React with alcohols:
2.6 Esters
Receipt
Esters are mainly produced when carboxylic and mineral acids interact with alcohols:
Chemical properties
A characteristic property of esters is ability to undergo hydrolysis:
CHAPTER 3. ECOLOGICAL FEATURES OF STUDYING THE TOPIC: “OXYGEN-CONTAINING ORGANIC COMPOUNDS”
Phenols are among the most common pollutants entering aquatic environment with wastewater from oil refining, wood-chemical, coke-chemical, aniline-dye and other enterprises.
Phenols are oxy-substituted aromatic hydrocarbons(benzene, its homologues, naphthalene, etc.). They are usually divided into those that are volatile with water vapor (phenol, creosols, xylenols, etc.) and non-volatile phenols (di- and trioxy compounds). Based on the number of hydroxyl groups, monohydric, diatomic and polyatomic phenols are distinguished. Phenols in natural river conditions are formed during the metabolic processes of aquatic organisms, during the biochemical oxidation and transformation of organic substances.
Phenols are used for disinfection, making adhesives and phenol-formaldehyde plastics. They are part of the exhaust gases of gasoline and diesel engines, and are present in large quantities in wastewater from oil refining, wood chemical, aniline dyeing and a number of other enterprises. High concentrations of these compounds are found in wastewater from coke production plants, in which the levels of volatile phenols reach 250-350 mg/l, polyhydric phenols - 100-140 mg/l.
In natural waters, phenols are usually found in a dissolved state in the form of phenolates, phenolate ions and free phenols. They can enter into condensation and polymerization reactions, forming complex humus-like and other fairly stable compounds. Under natural conditions, the sorption of phenols by suspended matter and bottom sediments is usually insignificant. In areas of technogenic pollution, this process is more significant. Typical phenol contents in unpolluted and slightly polluted waters do not exceed 20 µg/l. In polluted waters their content reaches tens and hundreds of micrograms per liter.
The good solubility of phenols and the presence of appropriate sources determine the high intensity of their pollution of river waters in urban agglomerations, where their content reaches tens and even hundreds of micrograms per liter of water. For example, in the waters of the Rhine and Main rivers in the early 1980s. Increased concentrations of many phenols coming from wastewater were consistently observed. A reliable indicator of the degree of water contamination with phonols is the number of phenol-degrading bacteria. Saprophytic anaerobes are usually present in places where phenol is intensively destroyed, and under polluted conditions the amount of phenol itself (carbolic acid, hydroxybenzene) and saprophytic bacteria in bottom silt and in the bottom layer of water is much greater than in the water column. Phenols undergo relatively intensive biochemical and chemical oxidation, depending on water temperature, pH value, oxygen content and a number of other factors. In river flow, there is a close inverse relationship between water temperature and the transfer of phenols, which is explained by the microbial oxidation of these compounds.
Phenols have a toxic effect and worsen the organoleptic properties of water. The toxic effect of phenols on fish increases markedly with increasing water temperature. It is known that phenols play an important role in the accumulation processes heavy metals higher aquatic plants, change the regime of nutrients and gases dissolved in river water. In the process of biochemical destruction of phenol, all elements of the hydrochemical regime change: a decrease in oxygen concentrations, an increase in color, oxidability, BOD, alkalinity and aggressiveness (in relation to, for example, concrete) of water. The products formed in the processes of destruction and transformation of phenol may be more toxic in their properties (for example, pyrocatechin, which, moreover, is capable of forming chelates with many metals).
Monohydric phenols are strong nerve poisons that cause general poisoning of the body also through the skin, which has a cauterizing effect. Human poisoning with phenol occurs when its vapors and aerosols are inhaled, resulting from the condensation of vapors, the substance entering the gastrointestinal tract and being absorbed through the skin.
Acute human poisoning was observed mainly when phenol came into contact with the skin. The effect of phenol on the skin depends less on the concentration of the solution and more on the duration of exposure.
Hygienic regulation of phenol: - in the air of the working area, the maximum permissible concentration is 0.3 mg/m3, vapors, hazard class II, the substance is dangerous if ingested through intact skin; - in atmospheric air the maximum single MPC is 0.01 mg/m3, the daily average is 0.01 mg/m3, hazard class II; MPC has not been established in soil.
Chemical pollution of the environment is the most noticeable and noticeable. The air in residential premises contains oxides of nitrogen, sulfur, carbon, volatile organic compounds, suspended substances, and microorganisms.
There are several types of indoor air pollution sources: high temperature sources, Construction Materials and waste products of humans and living organisms. Human waste products are represented mainly by carbon monoxide, hydrocarbons, ammonia, aldehydes, ketones, alcohols, and phenols. In small quantities, as a result of human activity, acetone, acetaldehyde, isoprene, ethanol, ethyl mercaptan, hydrogen sulfide, carbon disulfide, as well as nitrotoluene, coumarin, and naphthalene are released. Dust is also a source of indoor air pollution as a mechanical suspended impurity (up to 250 thousand dust particles per liter of air) and as a place of residence for dust mites, the number of which in a gram of dust can reach 2-3 thousand. The waste products of ticks are a number of chemicals that negatively affect respiratory system humans and can cause allergic reactions.
Polymers, varnishes, paints
A significant portion of pollutants in indoor air is caused by the use of polymer and paint materials. When the temperature rises in a room decorated with polymer materials, a specific smell of plastic appears due to the release of isoprene, styrene, benzene and other substances.
Polystyrene plastics are a source of release of formaldehyde, styrene, ethylbenzene, isopentane, and butanol. At 20 degrees Celsius, styrene in the amount of 26.2 μg/kg, ethylbenzene - 12.3 μg/kg, and butanol - 21.5 μg/kg were found in the products released from suspension polystyrene. Foamed polystyrene is a source of release of isopentane - 10.7 mg/kg, ethylbenzene - 0.5 mg/kg, butene, phenol and other substances. When studying the composition of products released from polyvinyl chloride at 20 degrees, benzene and ethylene were identified in trace amounts using gas chromatography. Plasticized polyvinyl chloride is a source of release of plasticizers of the phthalates group.
Swedish scientists have estimated the amount of phthalates entering Swedish waterways from cleaning linoleum floors alone at 60 tons per year. Carpets, curtains, and furniture made with synthetic fibers are a source of release of acetonitrile, ammonia, hydrogen chloride and hydrogen cyanide. Paints and varnishes pollute the air with substances contained in solvents: benzene, toluene, white spirit, xylene, etc. Chipboards and some parts of furniture fittings can be a source of release of phenol and formaldehyde into the environment. Most aldehydes and ketals are capable of causing primary irritation to the skin, eyes and breathing. This property is in to a greater extent appears in the lower members of the series, in those that are unsaturated in the aliphatic chain, and in halogen-substituted members. Aldehydes may have an analgesic effect, but their irritant effects may cause staff to limit exposure before it occurs. Irritation of the mucous membranes may be due to the ciliostatic effect, which damages the hair-like cilia that line the airways and purify the air. The degree of toxicity within the aldehyde family varies widely. Some of the aromatic and aliphatic aldehydes are quickly broken down during metabolism and do not have harmful effects; they are considered safe for use in foods as flavoring agents. However, other members of the family are known (or suspected) to be carcinogenic, and when possible contact they must be handled with appropriate precautions. Some aldehydes are chemical mutagens, and some are allergens. Another toxic effects aldehydes are associated with their hypnotic effect. More detailed information regarding some members of the aldehyde family is given below and also contained in the accompanying tables. Acetaldehyde is a mucosal irritant and also has a general narcotic effect on the central nervous system. Low concentrations cause irritation of the mucous membrane of the eyes, nose and upper respiratory tract, as well as bronchial catarrh. Extensive contact may result in damage to the horny epithelium. High concentrations cause headache, stupor, bronchitis and pulmonary edema. Swallowing causes nausea, vomiting, diarrhea, narcotic state and respiratory arrest; death may occur due to kidney damage, fatty degeneration of the liver and heart muscle. Acetaldehyde enters the bloodstream as a metabolite of ethyl alcohol and will cause facial flushing, hand tremors and other unpleasant symptoms. This effect is enhanced medicine teturam (Antabuse), and exposure to industrial chemicals such as cyanamide and dimethylformamide.
In addition to its direct effects, acetaldehyde belongs to group 2B carcinogens, that is, according to the classification International agency It is considered possibly carcinogenic to humans and carcinogenic to animals by the IARC. In various experiments, acetaldehyde stimulated chromosome aberration. Repeated exposure to acetaldehyde vapor causes dermatitis and conjunctivitis. With chronic intoxication, the symptoms are similar to those of chronic alcoholism: weight loss, anemia, delirium, visual and auditory hallucinations, weakened intelligence and mental disorders. Acrolein is a common air pollutant found in exhaust gases from internal combustion engines, which contain a large number of different aldehydes. The concentration of acrolein increases when using diesel fuel or fuel oil. In addition, acrolein is found in large quantities in tobacco smoke, not only in the form of macroparticles but also - mainly - in gaseous form. When combined with other aldehydes (acetic aldehyde, propionaldehyde, formaldehyde, etc.) it reaches concentrations that appear to make it one of the most dangerous aldehydes in tobacco smoke. Thus, acrolein is possible danger for industrial premises and the environment. Acrolein is toxic and highly irritating, and its high vapor pressure can quickly lead to hazardous concentrations in the atmosphere. Acrolein vapors can cause damage to the respiratory tract, and both the vapors and the liquid itself are dangerous to the eyes. Contact with skin may cause serious burns. Acrolein is very easy to detect because severe irritation occurs at concentrations well below the health-hazard threshold (its powerful lachrymatory effect at very low levels in the atmosphere () causes people to run away from the contaminated area in search of protective equipment). Consequently, most exposure to acrolein results from leakage from pipelines or containers. Serious chronic consequences, such as cancer, cannot be completely excluded. The greatest danger comes from inhaling acrolein vapors. The result may be irritation of the nasopharynx, chest tightness, shortness of breath, nausea and vomiting. The bronchopulmonary consequences of acrolein damage are very serious; even after recovery, persistent radiological and functional impairments remain. Experiments on animals have shown that acrolein is a vesicant toxicant; it damages the mucous membrane of the respiratory tract to such an extent that respiratory function is completely blocked within 2 to 8 days. Repeated skin contact may lead to dermatitis and allergic reactions. Not so long ago its mutagenic properties were discovered. Using Drosophila as an example, Rapaport showed this back in 1948. The purpose of the study was to find out whether lung cancer, the connection of which with tobacco abuse is undeniable, is caused by acrolein present in smoke, and also whether acrolein contained in burnt oil is the cause of some forms of cancer digestive tract, which have been found to be associated with eating burnt butter. Recent studies have shown that acrolein is mutagenic in some cells (seaweeds such as Dunaliella bioculata) but not in others (yeasts such as Saccharomices cerevisiae). If acrolein is mutagenic for a cell, then ultrastructural changes are detected in its nucleus, similar topics that occur when seaweed is irradiated with X-rays. Acrolein also has a variety of effects on DNA synthesis, acting on several enzymes. Acrolein very effectively blocks the work of the cilia of bronchial cells, which help cleanse the bronchi. In combination with its inflammatory effect, this gives a high probability of chronic bronchial diseases. Chloroacetaldehyde has the ability to severely irritate not only mucous membranes (it is dangerous to the eyes even in the form of vapor and can cause irreversible damage), but also the skin. It causes burn-like injuries upon contact with a 40% solution and noticeable irritation upon prolonged or repeated exposure to a 0.1% solution. Precautionary measures should include preventing any contact with chloroacetaldehyde and controlling its levels in the atmosphere. Chloral hydrate is primarily excreted by humans first as trichloroethanol and then, over time, as trichloroacetic acid, which can reach half the dose upon repeated exposure. In large doses, chloral hydrate acts like a drug and depresses the respiratory center. Cretonaldehyde is a strong irritant and can cause corneal burns; it is similar in toxicity to acrolein. There have been cases of allergic reactions in exposed workers, and some mutagenicity tests have yielded positive results. In addition to being a significant fire hazard, P-dioxane is also classified as a Group 2B carcinogen by the IARC, meaning it is an established animal carcinogen and a possible human carcinogen. Animal studies of the effects of inhaling P-dioxane have shown that its vapor can cause a narcotic state, damage to the lungs, liver and kidneys, irritation of the mucous membranes, pulmonary congestion and edema, changes in behavior and an increase in the number of blood cells. Large doses of P-dioxane contained in drinking water led to the development of tumors in rats and guinea pigs. Experiments with animals have also shown that P-dioxane is rapidly absorbed through the skin, causing incoordination, a drugged state, erythema, and damage to the kidneys and liver.
Formaldehyde and its polymer derivative paraformaldehyde. Formaldehyde readily polymerizes in both liquid and solid states, resulting in a mixture of chemical compounds known as paraformaldehyde. This polymerization process is slowed down by the presence of water, and therefore industrially used formaldehyde (known as formalin or formol) is water solution, containing from 37 to 50 weight percent formaldehyde; 10 to 15% methyl alcohol is added to these aqueous solutions as a polymerization inhibitor. Formaldehyde is toxic if swallowed or inhaled, and may cause skin damage. During metabolism, it turns into formic acid. The toxicity of polymerized formaldehyde is potentially similar to that of the monomer because depolymerization occurs when heated. Exposure to formaldehyde causes acute and chronic reactions. Formaldehyde has been proven to be a carcinogen in animals; According to the IARC classification, it belongs to group 1B, as a possible carcinogen to humans. Therefore, when working with formaldehyde, the same precautions should be taken as for all carcinogens. Low concentrations of formaldehyde vapor cause irritation, especially to the eyes and respiratory tract. Due to the solubility of formaldehyde in water, its irritant effect is limited to the upper respiratory tract. Concentrations of the order of cause mild formation of the eyes and nasopharynx; when the feeling of discomfort increases quickly; When there is serious difficulty breathing, burning in the eyes, nose and trachea, severe lacrimation and coughing. Concentrations of 50 to cause chest tightness, headache, palpitations, and in severe cases lead to death due to swelling or spasm of the larynx. Burns may also occur.
Formaldehyde reacts with hydrogen chloride, and it has been reported that this reaction can produce small amounts of secondary chloromethyl ether, which is a dangerous carcinogen, in humid air. Further studies showed that at normal ambient temperature and humidity, even at very high concentrations of formaldehyde and hydrogen chloride, methyl chloride ether is not formed in quantities exceeding the sensitivity threshold. However, the US National Institute for Occupational Safety and Health (NIOSH) has recommended that formaldehyde be treated as a potential industrial carcinogen because some tests have shown it to be mutagenic and can cause nasal cancer in rats and mice, especially when combined with salt fumes. acids.
Glutaraldehyde is a relatively weak allergen that can cause allergic dermatitis, and in combination with its irritant effect, its allergenic properties can also cause allergic respiratory diseases. It is a relatively strong skin and eye irritant.
Glycidaldehyde is a highly reactive chemical that is classified in IARC Group 2B as a possible human carcinogen and an established animal carcinogen. Therefore, the same precautions should be taken when handling this substance as for other carcinogens.
Metacetaldehyde, if ingested, can cause nausea, severe vomiting, abdominal pain, muscle tension, convulsions, coma, and death from respiratory arrest. Ingestion of paraacetaldehyde usually causes sleep without respiratory depression, although deaths due to respiratory arrest and circulatory arrest have been reported following large doses. Dimethoxymethane can cause liver and kidney damage, and in acute exposure is irritating to the lungs.
DERIVATIVES OF CARBOXYLIC ACIDS
Of this group, the most widely used are dalapon, sodium trichloroacetate, amiben, banvel-D, 2,4-dichlorophenoxyacetic acid (2,4-D) and its sodium and amine salts, butyl, crotyl and octyl esters; 2M-4Х, 2.4-М, 2М-4ХМ, 2М-4ХП, kambilene, dactal, propanide, ramrod, solan, etc. external environment they are moderately stable and have little effect on the hydrochemical regime. Butyl ether 2,4-D gives water a “pharmacy” smell at a concentration of 1.62 mg/l and a taste at 2.65 mg/l.
Toxicity. Carboxylic acid derivatives have a similar mechanism of action. They affect the nervous system of fish, cause functional and morphological changes in the liver, kidneys, hematopoietic tissue, reproductive organs, etc. Propanide and other anilides, in addition, have a hemolytic effect. Drugs of the 2,4-D group disrupt the reproductive function of animals.
CHAPTER 4. MY LESSONS
Lesson: Oxygen-containing organic compounds
Goals . Summarize students' knowledge on this topic in game form check their level of knowledge and skills.
Equipment . On the demonstration table are chemical reagents, cosmetics, fragrances, laundry detergents, apples, bread, potatoes, and medicines.
Motto If your path leads to knowledge of the World, No matter how long and difficult it may be - go ahead! (Firdousi)
DURING THE CLASSES
Teacher. “I want to become a chemist!” - this is how high school student Justus Liebig answered the question of the director of the Darmstadt gymnasium about the choice future profession. This caused laughter from the teachers and schoolchildren who were present during the conversation. The fact is that in Liebig’s time in Germany, and in most other countries, such a profession was not taken seriously. Chemistry was considered as an applied part of natural science and, although theoretical ideas about substances were developed, experimentation was most often not given due importance.
Nowadays, the desire to become a chemist does not make anyone laugh; on the contrary, the chemical industry is constantly in need of people who combine extensive knowledge and experimental skills with a love of chemistry. The role of chemistry in various fields of technology and Agriculture is increasing all the time. Without numerous chemicals and materials, it would be impossible to increase the power of mechanisms and vehicles, expand the production of consumer goods and increase labor productivity. The chemical and pharmaceutical industry produces a variety of medicines that improve human health and prolong life.
To improve the well-being and better meet the needs of the population, skilled workers, engineers and scientists are needed. And it all starts with the school laboratory. So, first round.
I round School student laboratory
Exercise (1st laboratory I). Get aldehyde.
Heat a copper spiral in the flame of an alcohol lamp and lower it into a test tube with alcohol. A sharp smell of aldehyde is felt, the spiral becomes shiny. Reaction equation:
Exercise (2nd laboratory). Obtain carboxylic acid.
Add 1.5 ml of H 2 SO 4 (conc.) to 2 g of sodium acetate CH 3 COONa, close the test tube with a stopper with a gas outlet tube and heat the mixture with the flame of an alcohol lamp. The reaction occurs:
The resulting acetic acid ( t kip = 118 °C) is distilled off and collected in an empty test tube.
Exercise (3rd laboratory). Obtain ester.
Pour 1 ml of CH 3 COOH and C 2 H 5 OH into a test tube, add 0.5 ml of H 2 SO 4 (conc.) and heat for 5 minutes with a spirit lamp, without bringing to a boil. Cool the contents of the test tube and pour into another test tube with 5 ml of water. The formation of a layer of liquid immiscible with water—ethyl acetate ester—is observed. Reaction equation:
2nd round Fragrant retort
Teacher. “And she stopped near a seller of incense, and took from him ten different waters: rose water mixed with musk, orange water, water from white water lilies, from willow and violet flowers, and five others. And she bought another loaf of sugar, a bottle for spraying, a bag of incense, ambergris, musk and wax candles from Alexandria, and she put it all in the basket and said: “Take the basket and follow me...”
This is an excerpt from the story of a porter and three women from Baghdad, one of the most beautiful tales of the Arabian Nights. Wonderful flower water, fragrant aromatic substances, just like gems and exquisite dishes, in the countries of the East were once a sign of wealth. Many centuries ago, the Arabs already knew various ways to obtain aromatic substances from plants and animal secretions. In the perfume shops of oriental bazaars, numerous merchants offered a rich selection of exquisite aromatic substances.
In medieval Europe, perfume was not used. After ancient times, they reappeared only in the Renaissance. But already at the court of Louis XIV, ladies smothered themselves heavily in order to drown out bad smell emanating from the body - it was not customary to wash.
We always enjoy pleasant aromas. However, tastes have changed - the intoxicating incense of the East and the sharp, intrusive aroma of perfumes of the Renaissance gave way to subtle fantasy (i.e., created by the imagination of perfumers) aromas. And something else has changed. Magnificent perfumes are available to all women today. If previously it was necessary to cultivate roses in vast fields, collect their flowers and process them in order to obtain just a few kilograms of rose oil, today chemical plants produce wonderful aromatic substances and, moreover, often with completely new shades of odors. Natural aromatic substances can be obtained from plants, in the special cells of which they are usually found in the form of small droplets. They are found not only in flowers, but also in leaves, in the peel of fruits and sometimes even in wood.
Laboratories display home-made fragrances.
Peppermint oil (1st laboratory)
From 50 g of dried peppermint we can extract 5-10 drops of peppermint oil. It contains, in particular, menthol, which gives it its characteristic smell.
Peppermint oil is used in large quantities to make cologne, eau de toilette and hair products, toothpastes and elixirs.
Perfume (2nd laboratory)
To obtain a pleasant smell, you will need, first of all, citrus oil, which we get from the peels of oranges or lemons. For this purpose, grate the peel, wrap it in a piece of durable cloth and squeeze it out thoroughly. Mix 2 ml of cloudy liquid that seeped through the fabric with 1 ml of distillate obtained from soap. Now we need a floral scent. We will create it by adding 2-3 drops of lily of the valley oil to the mixture. Drops of methyl salicylate, caraway oil, and a small addition of vanilla sugar improve the aroma. Finally, dissolve this mixture in 20 ml of pure alcohol or, in extreme cases, an equal volume of vodka, and our perfume is ready. We get it by heating 3.5 parts of powdered gelatin with 65 parts of rose water (rose petals are kept in water for several days) and 10 parts of honey. While stirring, add another mixture containing 1 part perfume, 1.5 parts alcohol and 19 parts glycerin to the heated mixture. In a cold place, the mass thickens and a ready-to-use jelly-like cream is formed. Teacher. “Man is what he eats” - this statement by Ludwig Feuerbach contains the whole essence of naive materialism. In our time, of course, we cannot agree with such an opinion, which does not take into account the fact that man represents a special, qualitatively new, highest stage of development of living organisms on Earth. But be that as it may, we can say that the human body is truly like a chemical plant with extremely complex production technology. In the human body, without the use of strong acids, as well as high pressures and temperatures, the most complex chemical transformations are carried out with excellent yield. The human body not only cannot grow and develop, but also simply exist without an influx of organic substances. Unlike plants, it cannot itself create organic compounds from inorganic raw materials. In addition, the body requires energy - both to maintain the appropriate body temperature and to perform work. These same organic substances enter our body with food, and when they break down, energy is released. Exercise
(1st laboratory). Prove that a ripe apple contains glucose. (React the silver mirror with apple juice.) Exercise(2nd laboratory). Detect starch in food. (Carry out an iodine-starch reaction, for example, on a potato cut.) Exercise(3rd laboratory). Define acetic acid. (Use indicator - blue litmus and soda powder.) Teacher
.
Thanks to the iodine-starch reaction, it was more than once possible to expose swindlers who were selling sandwiches by passing off margarine as butter. According to technical conditions, margarine produced by industry must contain the addition of sesame oil. The latter gives a red color with furfural and hydrochloric acid. Since 1915, it was allowed to replace sesame oil with potato starch. Margarine contains 0.2% starch. Teacher
. Detergents became available to everyone only thanks to chemistry. In ancient Rome, rancid urine was valued as the most common cleaning agent. In those days, it was specially collected, it was an object of trade and exchange. Toilet soap has been a luxury item for centuries. Effective detergents, toilet soaps, stain removers and many other things we can't live without were created by chemists in research laboratories. These tools make our household work incredibly easier. Exercise
(1st laboratory). Test washing solutions detergents phenolphthalein. Which detergent would you use to wash wool or natural silk items? Exercise
(2nd laboratory). Try dissolving vegetable oil in various solvents - water, ethanol, gasoline. What will you use to remove the grease stain? Exercise
(3rd laboratory). Experiments with hard water - gradually adding solutions of various detergents to it. In what case do you have to add more solution until a stable foam forms? Which drug does not lose its cleaning effect in hard water? What are the advantages and disadvantages of synthetic detergents?
Fragrances
Honey hand cream (3rd laboratory)
Round III - Food as chemical compounds
IV round. Washing detergents
Natural and synthetic detergents
Teacher . So, we see that chemistry is moving forward ever faster, helping to make our lives more beautiful and easier. She contributes to the fight to ensure that our land can feed all of humanity. But the creators of the chemistry of tomorrow will be you, today’s schoolchildren. You have to, not without hard work, acquire knowledge so that later, using it, you can benefit people.
The results are summed up.
Open lesson in chemistry: "Areas of application of alcohols, aldehydes and carboxylic acids."
Goals lesson:
· Generalization of knowledge on the use of alcohols, aldehydes and carboxylic acids.
· Environmental protection and life safety in the production and use of alcohols, aldehydes and carboxylic acids.
· Expanding students' horizons about enterprises in their native region (students prepare speeches in advance).
Motto: Serving the Fatherland is the noble role of chemistry.
During the classes
Teacher: Today in class we will talk not only about the practical application of some organic substances, but also about the safety of people’s lives. Most branches of the chemical industry produce useful products (we have no doubt about this), but how can we ensure that waste from production does not pollute the environment or adversely affect people’s health?
Student: Methanol is used to produce a large number of different organic substances, in particular formaldehyde
and methyl methacrylate
which are used in the production of phenol-formaldehyde resins and organic glass. Methanol is used as a solvent, extractant, and in a number of countries as a motor fuel, since its addition to gasoline increases the octane number of the fuel and reduces the amount of harmful substances in the exhaust gases. This shows concern for people. (A detailed abstract on the use of alcohols is being prepared.)
Teacher: And now, let’s conduct a “chemical relay race”. (5 minutes)
Students complete the task.
Write down reaction equations that can be used to carry out the following transformations: ethane – ethylene – ethyl alcohol – ethanal – acetic acid.
(To check, on the back of the board, one student completes the same task.)
C 2 H 6 -> C 2 H 4 -> C 2 H 5 OH -> CH 3 CHO -> CH 3 COOH
1. Ni C 2 H 6 -> C 2 H 4 + H 2 n+, cat.
2. C 2 H 4 + H 2 O -> C 2 H 5 OH
3. C 2 H 5 OH + CuO -> CH 3 CHO + Cu + H 2 O
4. CH 3 CHO + 2Cu(OH) 2 -> CH 3 COOH + Cu 2 O + 2H 2 O
Teacher: Chemistry has enormous potential. Let's take, for example, medicines - substances that are so necessary for human health. Even they can be extremely dangerous if used unwisely, illiterately, for example, when self-medicating.
Student: Chemistry is very closely related to medicine. The connection arose a long time ago. Back in the 16th century, the medical field was widely developed, the founder of which was the German physician Paracelsus.
Aspirin or acetylsalicylic acid
one of the drugs that is widely used as an antipyretic, analgesic and antirheumatic agent. Aspirin is an acid, and too much of it can irritate the stomach lining and cause ulcers. But concern for people's health helped find a way out of this situation. It turned out that the substances contained in cherries act better than aspirin.
JSC Krasnogorskleksredstva produces not only packaged medicinal herbs, but also liquid medicines and herbal teas. And adding lemon juice to tea will help relieve heart pain.
According to botanists, the homeland of lemon is India, where it grows wild in the mountains, at the foot of the Himalayas, from where it later spread to the countries of Southeast Asia and, much later, to Europe. In Russia, they really became acquainted with lemon only in the second half of the 17th century, when its trees were first brought from Holland to Moscow and planted in the Kremlin “greenhouse chambers.” IN early XVII V. In the estates of landowners, the “fashion” for growing lemons for the purpose of producing fruits quickly spread.
By the way, in our country this tradition is still maintained. For example, in the city of Pavlov, Nizhny Novgorod region, many people have 4–5 small lemon trees at home. This is where the famous indoor variety Pavlovsky came from. However, the indoor tree of this lemon gives, with careful attention, proper care 10–16 fruits per year. What determines the benefits of lemon? First of all, of course, ascorbic acid, or vitamin C, the medicinal value of which is known to many. This vitamin is an anti-scurvy remedy. Even during the great sea voyages, Europeans widely used lemon for this purpose. It is known that the famous navigator J. Cook took a supply of these fruits with him on ships, and in 1795 a decree was issued in England, according to which ship crews were ordered to be given daily portions of lemon juice.
Today it is known that vitamin C increases the body's resistance to infectious diseases, especially the so-called colds. That is why lemons can be recommended (along with other fruits and vegetables) as a means for nonspecific prevention of influenza and influenza-like diseases. Moreover, saturation with this vitamin increases resistance to the effects of cold. In addition, this vitamin has the ability to accelerate the healing of wounds, burns and bone fractures, and promotes faster recovery from rheumatism, tuberculosis, and allergic lesions. According to some reports, patients with various infections experience relief when treated with ascorbic acid.
It is curious that there is much more vitamin C in the lemon peel than in its pulp. Therefore, you need to eat the entire fruit without leaving a trace. In order to satisfy the daily requirement of an adult for this vitamin, you need to consume about 100 grams of lemon daily, i.e. two small or one large lemon fruit. However, not everyone likes sour.
And lemon is really sour.
(A detailed abstract is being prepared.)
Teacher: Now let's listen to a message about cosmetics.
Student: Excavations of ancient settlements indicate that people have always had a desire to paint their bodies.
In the distant past, only natural substances were used as cosmetics. With the development of chemistry, in addition to natural substances, synthetic ones began to be used.
For aromatic substances, the most modern methods of organic synthesis are used. Currently, methods for the synthesis of almost all fragrant substances previously extracted from natural raw materials have been developed, and a number of new ones have been created that were not found in nature. Menthol with the smell of peppermint is now obtained from chemical, rather than natural, raw materials; citral, which smells like lemon; vanillin; iron with a delicate aroma of violet and many others.
But Lauren Cosmetics LLC, located in Dedovsk, Moscow Region, produces products from natural raw materials. These are possible coloring shampoos, deodorants that do not contain freon and much more. (A detailed abstract is being prepared.)
Teacher: Let's listen to a message about the use of formic and lactic acids.
Student: Formic acid.
Ants of the genus Formika use various acids as a means of communicating with each other, just like many social insects. Formic acid, secreted by ants at the moment of danger, serves as a signal for all other individuals of this species and is a means of defense when attacked by predators. Thanks to this acid, ants do not have many enemies.
Lactic acid
Lactic acid (C 3 H 6 O 3) is an intermediate metabolic product in warm-blooded animals. The smell of this acid is picked up by blood-sucking insects, in particular mosquitoes, at a considerable distance. This allows insects to find their prey.
Teacher: The last issue we will discuss in class today is chemistry and food.
Student: Man is a strange creature. At first, despite common sense destroys his own health and then strives to improve it. The reason is basic illiteracy. Our country is being overwhelmed by a wave of imported food products. Suppliers from the Netherlands, Denmark, Germany, USA, France, Israel. However, in every developed country there are three categories of food products: for the domestic market, for developed countries, for developing countries, including, unfortunately, for Russia. How to protect yourself?
It is necessary to become familiar with the labels on the packaging of confectionery products, drinks, margarine, etc. Let’s pay attention to the letter E.
· E 100 – E 182 – dyes (carmine – red; turmeric – yellow; sugar color(caramel) – dark brown).
· E 200 – E 299 – preservatives are substances, the addition of which allows to slow down or prevent the development of microflora.
· E 300 – E 399 – substances that slow down fermentation processes.
· E 400 – E 409 – stabilizers, provide products with long-term storage.
· E 500 – E 599 – emulsifiers, these substances help maintain uniform distribution of the dispersed phase in the medium, for example, vegetable oils, beer.
· E 600 – E 699 – flavorings, i.e. compounds that enhance or impart flavor to foods.
· E 900 – E 999 – anti-flaming agents that prevent flour, salt, soda, etc. from caking.
The State Sanitary and Epidemiological Supervision Service and the Society for the Protection of Consumer Rights do not recommend consuming food products containing additives labeled:
· E 131, E 141, E 215 – E 218, E 230 – E 232, E 239 – are allergens;
· E 121, E 123 – can cause gastrointestinal disorders, and in large doses, food poisoning;
· E 211, E 240, E 442 – contain carcinogens, i.e. can provoke the formation of tumors.
Application food additives is permissible only if they, even with prolonged use, do not threaten human health.
Teacher: In the town of Krasnogorsk near Moscow there is a confectionery factory “KONFAEL”. This factory produces confectionery products with natural fillings. Let's listen to a message about this wonderful factory. (The student makes a message.)
If you have time, you can ask intellectual questions. (5 minutes)
· This substance, or rather its solution, is used for preserving biological preparations, and thanks to its vapor contained in wood smoke, fish and sausages are smoked.
Answer: formaldehyde.
· Modern recommendations for proper nutrition do not differ from those expressed more than 4 thousand years ago in the Bible and more than 2.5 thousand years ago by Hippocrates. One such piece of advice is: “Don’t fry food, steam it, boil it, bake it.” Why?
Answer: When frying, condensed aromatic substances are formed, for example benzopyrene (3,4 - benzyrene).
Answer: Alcohol dissolves well in water and will accumulate where it is most abundant - in the fetus, in the brain.
· Substances of which classes of organic compounds are most often used in the perfume industry?
Answer: ethers, alcohols, aldehydes, arenes.
· What acids can be used in everyday life to remove fruit and rust stains?
Answer: lemon, apple, vinegar, oxalic.
or solve a problem.
In the pharmacy, a 10% solution of table salt is used to dissolve antibiotics. How much distilled water will be required to prepare 100 g of 10% NaCl solution?
1. 10% or 0.1
m(NaCI) = 100. 0.1 = 10 (g)
2. m (H 2 O) = 100 – 10 = 90 (g)
Answer: 90 g of water.
Teacher: Chemistry is an amazing science; it introduces a person to the world of various substances that surrounds us. Study chemistry and you will achieve it.
TASKS
Problem 1. Upon combustion organic matter weighing 4.8 g, 3.36 l of CO 2 (n.s.) and 5.4 g of water were formed. The vapor density of an organic substance for hydrogen is 16. Determine the molecular formula of the substance under study.
Solution. The combustion products of a substance consist of three elements: carbon, hydrogen, oxygen. It is obvious that this compound included all the carbon contained in CO 2 and all the hydrogen that passed into the water. But oxygen could join from the air during combustion, or it could be partially contained in the substance itself. To determine the simplest formula of a compound, we need to know its elemental composition. Let's find the number of reaction products (in moles):
n(CO 2) = V(CO 2) / V M = 3.36 l: 22.4 l/mol = 0.15 mol n(H 2 O) = m(H 2 O) / M(H 2 O) = 5.4 g: 18 g/mol = 0.3 mol Therefore, the original compound included 0.15 mol of carbon atoms and 0.6 mol of hydrogen atoms: n(H) = 2n(H 2 O), since One molecule of water contains two hydrogen atoms. Let's calculate their masses using the formula: m = n x M
m(H) = 0.6 mol x 1 g/mol = 0.6 g
m(C) = 0.15 mol x 12 g/mol = 1.8 g
Let's determine whether oxygen was included in the original substance:
m(O) = 4.8 - (0.6 + 1.8) = 2.4 g
Let's find the number of moles of oxygen atoms:
n(O) = m(O) / M(O) = 2.4 g: 16 g/mol = 0.15 mol
The ratio of the number of atoms in the molecule of the original organic compound proportional to their mole fractions:
n(CO 2) : n(H) : n(O) = 0.15: 0.6: 0.15 = 1: 4: 1
We take the smallest of these values (0.15) as 1, and divide the rest by it.
So, the simplest formula of the starting substance is CH 4 O. However, according to the conditions of the problem, it is necessary to determine the molecular formula, which in general is as follows: (CH 4 O) x. Let's find the value of x. To do this, compare the molar masses of the original substance and its simplest formula:
x = M(CH 4 O) x / M(CH 4 O)
Knowing the relative density of the starting substance with respect to hydrogen, we find the molar mass of the substance:
M(CH 4 O) x = M(H 2) x D(H 2) = 2 g/mol x 16 = 32 g/mol
x = 32 g/mol / 32 g/mol = 1
There is a second option for finding x (algebraic):
12x + 4x + 16x = 32; 32 x = 32; x = 1
Answer. The formula of the original organic substance is CH 4 O.
Problem 2. What volume of hydrogen (n.s.) will be obtained by reacting 2 mol of sodium metal with a 96% (by weight) solution of ethanol in water (V = 100 ml, density d = 0.8 g/ml).
Solution. In the problem statement, the quantities of both reagents are given - this is a sure sign that one of them is in excess. Let's find the mass of ethanol introduced into the reaction:
m(solution) = V x d = 100 ml x 0.8 g/ml = 80 g m(C 2 H 5 OH) = (m(solution) x w%): 100% = 80 g x 0.96 = 76.8 g
(1) 2C 2 H 5 OH + 2Na = 2C 2 H 5 ONa + H 2
for 2 moles of ethanol - 2 moles of sodium - 1 moles of hydrogen
Let's find the given amount of ethanol per mole:
n(C 2 H 5 OH) = m(C 2 H 5 OH) / M(C 2 H 5 OH) = 76.84 g: 46 g/mol = 1.67 mol
Since the given amount of sodium was 2 mol, sodium is present in excess in our problem. Therefore, the volume of hydrogen released will be determined by the amount of ethanol:
n 1 (H 2) = 1/2 n(C 2 H 5 OH) = 1/2 x 1.67 mol = 0.835 mol V 1 (H 2) = n 1 (H 2) x V M = 0.835 mol x 22 .4 l/mol = 18.7 l
But this is not the final answer. Be careful! The water contained in the alcohol solution also reacts with sodium to release hydrogen.
Let's find the mass of water:
m(H 2 O) = (m(solution) x w%): 100% = 80 g x 0.04 = 3.2 g n(H 2 O) = m(H 2 O)/M(H 2 O ) = 3.2 g: 18 g/mol = = 0.178 mol
(2) 2H 2 O + 2Na = 2NaOH + H 2
for 2 moles of water - 2 moles of sodium - 1 moles of hydrogen
The amount of sodium remaining unconsumed after the reaction with ethanol will be: n(Na, remainder) = 2 mol - 1.67 mol = 0.33 mol Thus, and compared to a given amount of water (0.178 mol), sodium still ends up in excess.
Let's find the amount and volume of hydrogen released by reaction (2): n 2 (H 2) = 1/2 n(H 2 O) = 1/2 x 0.178 mol = 0.089 mol V 2 (H 2) = n 2 (H 2) x V M = 0.089 mol x 22.4 l/mol = 1.99 l Total volume of hydrogen:
V(H 2) = V 1 (H 2) + V 2 (H 2) = 18.7 l + 1.99 l = 20.69 l
Answer: V(H 2) = 20.69 l
Task 3. Calculate the mass of acetic acid that can be obtained from 44.8 liters (n.s.) of acetylene if the losses at each stage of production average 20%.
Solution
C 2 H 2 + H 2 O =>(Hg 2+ ,H 2 SO 4)=> CH 3 CHO =>([O])=> CH 3 COOH
1 mol ==> 1 mol ==> 1 mol
Answer. m(CH 3 COOH) = 76.8 g
Task 4. When oxidizing a mixture of benzene and toluene with an acidified solution of potassium permanganate upon heating, 8.54 g of monobasic organic acid was obtained. When this acid interacts with an excess of an aqueous solution of sodium bicarbonate, a gas is released, the volume of which is 19 times less than the volume of the same gas obtained by complete combustion of the original mixture of hydrocarbons. Determine the masses of substances in the original mixture.
Solution
Only toluene is oxidized, resulting in the formation of benzoic acid:
5C 6 H 5 -CH 3 + 6KMnO 4 + 9H 2 SO 4 → 5C 6 H 5 -COOH + 3K 2 SO 4 + 6MnSO 4 + 14H 2 O
v(C 6 H 5 -COOH) = 8.54/122 = 0.07 mol = v(C 6 H 5 -CH 3).
When benzoic acid reacts with sodium bicarbonate, CO 2 is released:
C 6 H 5 -COOH + NaHCO 3 → C 6 H 5 -COONa + CO 2 + H 2 O.
v(CO 2) = v(C 6 H 5 -COOH) = 0.07 mol.
When a mixture of hydrocarbons is burned, 0.07 * 19 = 1.33 mol CO 2 is formed. From this amount during the combustion of toluene according to the equation
C 6 H 5 -CH 3 + 9O 2 → 7CO 2 + 4H 2 O
0.07*7 = 0.49 mol CO 2 is formed. The remaining 1.33-0.49 = 0.84 mol CO 2 are formed during the combustion of benzene:
C 6 H 6 + 7.5 O 2 → 6 CO 2 + ZH 2 O.
v(C 6 H 6) = 0.84/6 = 0.14 mol.
The masses of substances in the mixture are equal:
m(C 6 H 6) = 0.14-78 = 10.92 g, m(C 6 H 5 -CH 3) = 0.07*92 = 6.48 g.
Answer. 10.92 g benzene, 6.48 g toluene.
Problem 5. An equimolar mixture of acetylene and formaldehyde reacted completely with 69.6 g of silver oxide (ammonia solution). Determine the composition of the mixture (in % by weight).
Solution
Silver oxide reacts with both substances in the mixture:
HC ≡ CH + Ag 2 O → AgC ≡ CAg↓ + H 2 O,
CH 2 O + 2Ag 2 O → 4Ag ↓ + CO 2 + H 2 O.
(Reaction equations are written in simplified form).
Let the mixture contain x mol each of C 2 H 2 and CH 2 O. This mixture reacted with 69.6 g of silver oxide, which is 69.6/232 = 0.3 mol. The first reaction involved x moles of Ag 2 O, the second - 2 x moles of Ag 2 O, a total of 0.3 moles, which means that x = 0.1.
m(C 2 H 2) = 0.1 - 26 = 2.6 g; m(CH 2 O) = 0.1-30 = 3.0 g;
the total mass of the mixture is 2.6+3.0 = 5.6 g. The mass fractions of the components in the mixture are equal to:
(C 2 H 2) = 2.6/5.6 = 0.464, or 46.4%; (CH 2 O) = 3.0/5.6 = 0.536, or 53.6%.
Answer. 46.4% acetylene, 53.4% formaldehyde.
Task 6. A current of dry hydrogen chloride was passed through 10 g of a mixture of benzene, phenol and aniline, and 2.59 g of precipitate precipitated. It was filtered and the filtrate was treated with sodium hydroxide. The upper organic layer was separated, its mass decreased by 4.7 g. Determine the masses of substances in the original mixture.
Solution
When dry hydrogen chloride is passed through the mixture, a precipitate of phenylammonium chloride precipitates, which is insoluble in organic solvents:
C 6 H 5 NH 2 + HCl → C 6 H 5 NH 3 Cl ↓.
v (C 6 H 5 NH 3 Cl) = 2.59/129.5 = 0.02 mol, therefore v (C 6 H 5 NH 2) = 0.02 mol, m (C 6 H 5 NH 2) = 0.02. 93 = 1.86 g.
A decrease in the mass of the organic layer by 4.7 g occurred due to the reaction of phenol with sodium hydroxide:
C 6 H 5 OH + NaOH → C 6 H 5 ONa + H 2 O.
Phenol passed into aqueous solution in the form of sodium phenolate. m (C 6 H 5 OH) = 4.7 g. The mass of benzene in the mixture is 10 - 4.7 -1.86 = 3.44 g.
Answer. 1.86 g of aniline, 4.7 g of phenol, 3.44 g of benzene.
Problem 7. Ethylene hydrocarbon adds 6.72 l (N.S.) of hydrogen chloride. When the reaction product is hydrolyzed with an aqueous solution of sodium hydroxide upon heating, 22.2 g of saturated monohydric alcohol containing three methyl alcohols is formed. Determine the structure of the original hydrocarbon and the resulting alcohol.
Solution
Let's write down the reaction equations:
C n H 2n + HCl → C n H 2n+1 Cl,
C n H 2n+1 Cl + NaOH → C n H 2n+1 OH + NaCl.
v(HCl) = 6.72/22.4 = 0.3 mol.
According to the reaction equations,
v(C n H 2n+1 OH) = v(C n H 2n+1 Cl) = v(HCl) = 0.3 mol.
The molar mass of alcohol is:
M(C n H 2n+1 OH) = 22.2/0.3 = 74 g/mol, from which n = 4.
Therefore, the molecular formula of alcohol is C 4 H 9 OH.
Of the four alcohols of the composition C 4 H 9 OH, only the tertiary alcohol (2-methylpropanol-2, or tert-butyl alcohol) contains three methyl groups. The molecule of this alcohol includes a branched carbon skeleton, therefore, the original alkene with the composition C 4 H 8 also had a branched skeleton. This is 2-methylpropene. Reaction equations:
Answer. 2-methylpropene; tert-butanol.
Problem 8. A compound of unknown structure reacts slowly with sodium, is not oxidized by a solution of sodium dichromate, and reacts quickly with concentrated hydrochloric acid to form an alkyl chloride containing 33.3% chlorine by weight. Determine the structure of this compound.
Solution
The nature of the reactions with Na, with Na 2 Cr 2 O 7 and with HCl indicates that the unknown substance is a tertiary alcohol; when reacting with HCl, a tertiary alkyl chloride is formed:
ROH + HCl → RCl + H 2 O.
One mole of RCl contains one mole of Cl weighing 35.5 g, which is 33.3% of the total mass, therefore the molar mass of alkyl chloride is: M(RCl) = 35.5/0.333 = 106.5 g/mol, and the molar mass hydrocarbon radical is equal to: M(R) = 106.5-35.5 = 71 g/mol. The only radical with such a molar mass is C5H11.
Tertiary alcohols have the general formula:
One carbon atom out of five is connected to the hydroxyl group, and four atoms are part of three radicals. There is only one way to break four carbon atoms into three radicals: two CH 3 radicals and one C 2 H 5 radical. The desired alcohol is 2-methylbutanol-2:
Answer. 2-methylbutanol-2.
Problem 9. Arrange the following substances in order of increasing acidity: phenol, sulfurous acid, methanol. Give equations chemical reactions, confirming the correctness of the selected sequence.
Solution
The correct row looks like this:
CH 3 OH< С 6 Н 5 ОН < H 2 SO 3 .
Phenol is stronger than methanol because phenol reacts with alkali solutions, while methanol does not:
C 6 H 5 OH + NaOH = C 6 H 5 ONa + H 2 O, CH 3 OH + NaOH -I→
C 6 H 5 ONa + SO 2 + H 2 O = C 6 H 5 OH + NaHSO 3.
Phenol is displaced by sulfurous acid from sodium phenolate, therefore, sulfurous acid is stronger than phenol.
Problem 10. When an excess of sodium was applied to a mixture of ethyl alcohol and phenol, 6.72 liters of hydrogen (n.s.) were released. To completely neutralize the same mixture, 25 ml of a 40% solution (density 1.4 g/ml) was required. Determine the mass fractions of substances in the initial mixture.
Solution. Both ethanol and phenol react with sodium:
2C 2 H 5 OH + 2Na → 2C 2 H 5 ONa + H 2,
2C 6 H 5 OH + 2Na → 2C 6 H 5 ONa + H 2,
and with potassium hydroxide - only phenol:
C 6 H 5 OH + KOH → C 6 H 5 OK + H 2 O.
v(KOH) = 25-1.4-0.4 / 56 = 0.25 mol = v(C 6 H 5 OH).
From 0.25 mol of phenol in the reaction with sodium, 0.25/2 = 0.125 mol H 2 was released, and a total of 6.72/22.4 = 0.3 mol H 2 was released. The remaining 0.3-0.125 = 0.175 mol of H2 was released from ethanol, of which 0.175-2 = 0.35 mol was consumed.
Masses of substances in the initial mixture:
m(C 6 H 5 OH) = 0.25-94 = 23.5 g, m(C 2 H 5 OH) = 0.35-46 = 16.1 g. Mass fractions: (C 6 H 5 OH ) = 23.5 / (23.5+16.1) = 0.593, or 59.3%, (C 2 H 5 OH) = 16.1 / (23.5 + 16.1) = 0.407, or 40.7%.
Answer. 59.3% phenol, 40.7% ethanol.
Problem 11. Among the isomers of the composition C 7 H 7 OK, choose one from which a compound of the composition C 7 H 6 OBr 2 can be obtained in two stages.
Solution. Isomers of the composition C 7 H 7 OK can be derivatives of methylphenols (cresols) or benzyl alcohol - the simplest aromatic alcohol:
The substance with the composition C 7 H 6 OBr 2 is a dibromo derivative of C 7 H 8 O, which can be obtained by reaction with any inorganic (phenol, its homologues and aromatic alcohols are very weak acids). Two hydrogen atoms can be replaced by two bromine atoms in the benzene ring under the action of bromine water if an OH group is connected to the benzene ring, and one of the ortho- and para-positions relative to the OH group is occupied by a CH3 group (if all these positions are free from substituents, a tribromo derivative is formed). This condition is satisfied by 2-methylphenol (o-cresol) and 4-methylphenol (n-cresol). Thus, the reaction scheme is as follows (using the example of potassium 2-methylphenolate):
A similar scheme is valid for potassium 4-methylphenolate.
Answer. Potassium 2-methylphenolate or potassium 4-methylphenolate.
1. You can distinguish test tubes with benzene solutions of phenol and ethanol using:
a) sodium
b) potassium hydroxide
c) bromine water +
d) hydrogen chloride
2.What two organic substances are used to produce phenol in industry?
a) toluene
b) benzene +
c) ethylene
d) propylene +
3.Unlike ethanol, phenol reacts with:
a) potassium
b) aqueous solution of potassium hydroxide +
c) hydrogen chloride
d) potassium hydrogen sulfate
4. When saturated aldehydes interact with hydrogen, the following are formed:
a) carboxylic acids
b) ethers
c) secondary alcohols
d) primary alcohols +
5. When propanal is reduced, the following is formed:
a) propanoic acid
b) propanol-2
c) propanol-1 +
d) isopropyl alcohol
5. Formalin is called:
a) 35-40% solution of ethanol in water
b) 35-40% solution of methanal in water +
c) 35-40% solution of formic aldehyde in water +
d) 35-40% solution of formaldehyde in water +
6. Ethanal can be obtained:
a) dehydrogenation of ethanol +
b) oxidation of ethanol with oxygen in the presence of a catalyst +
7. Homologs of methanal are:
a) ethanal +
b) formalin
c) butanal +
d) ethanol
8. The main supplier of phenol and formaldehyde into the atmosphere:
a) medicine
b) wood processing industry +
V) chemical industry +
d) food industry
9. MPC of phenol in the air:
b) 20 mg/m 3
c) 17 mg/m 3
d) 5 mg/m 3 +
10. MPC of phenol in wastewater:
a) 20 mg/m 3
b) 1-2 mg/m 3 +
c) 12 mg/m 3
11. Maximum concentration of formaldehyde in the air:
a) 0.05 mg/m 3
b) 0.007 mg/m 3
c) 0.003 mg/m 3 +
12. The lethal dose of a 35% aqueous solution of formaldehyde is equal to:
13. Alcoholates are the interaction products:
a) phenols with active metals
b) alcohols with hydrogen halides +
c) alcohols with carboxylic acids
d) alcohols with active metals +
14. Indicate the names of primary alcohols:
a) ethanol +
b) isopropyl
c) propyl +
d) isobutyl
15. Indicate the names of the substances with which ethanol reacts:
a) hydrogen bromide +
b) acetic acid
c) methanol
d) solution of bromine in carbon tetrachloride
16. Using systematic nomenclature, name the compound that is predominantly obtained by the interaction of an aqueous solution of alkali with 2-chlorobutane:
a) 1-butene
b) 2-butene
c) 2- butanol +
d) 1-methyl-1-propanol
17. What compounds can be obtained by dehydration of 1-propanol under various conditions:
a) propylene +
b) methylpropyl ether
c) dipropyl ether +
d) 2-propanol
18. Ethylene glycol can be obtained:
a) interaction of acetylene with water +
b) interaction of ethylene with an aqueous solution of potassium permanganate +
c) interaction of 1,2-dichloroethane with an aqueous solution of alkali +
d) interaction of ethylene with water
19. What substances does glycerin react with?
a) potassium nitrate
b) nitric acid +
c) sodium +
d) freshly prepared copper hydroxide +
20. When oxidizing primary alcohol, you can get:
b) aldehyde +
c) carbon dioxide +
d) ether
21. When ethyl alcohol dehydrates, the following is formed:
a) ethylene
b) acetylene
c) propylene +
d) propine
22. Isomers of butanol-1 are:
a) isopropyl alcohol
b) propanol - 1
c) butanol-2 +
d) 2-methylpropanol-2 +
23. Ethanal can be obtained:
a) dehydrogenation of ethanol +
b) oxidation of ethanol with oxygen in the presence of a catalyst +
c) interaction of ethylene with water
d) interaction of acetylene with water +
24. What alcohol is formed during the reduction of 3-methylbutanal?
a) tertiary butyl
b) 2-methylbuganol-1
c) 3-methylbuganol-1 +
d) 2-methylbutanol-4
25. Homologs of methanal are:
a) ethanal +
b) formalin
c) butanal +
d) ethanol
26. What substance is an isomer of 2-methylpropanal?
a) 1-buganol
b) buganal
c) valeraldehyde +
d) pentanal +
27. Which of the listed substances are homologues of each other?
a) butyraldehyde +
b) ethanol
c) dimethyl ether
d) pentanal +
28. What compounds can be formed during the oxidation of ethanal under different conditions?
a) ethanol
) ethanoic acid
c) carbon dioxide
d) propionic acid
29. When ethylene is oxidized with oxygen in the presence of palladium and copper chlorides, the following is predominantly formed:
a) ethanol
b) ethanoic acid +
c) acetaldehyde
d) ethanal
30. What substances does methanoic acid react with?
a) methanol +
b) aluminum +
c) sodium carbonate +
31. Unlike other monocarboxylic acids of the limiting series, formic acid:
a) reacts with sodium
b) liquid under normal conditions
c) easily oxidizes +
d) is an aldehyde acid in structure +
32. When dissolved in water, 1 mole of acetic anhydride forms
a) 2 moles of ethanal
b) 2 mol ethanol
c) 2 mol acetic acid +
d) 1 mol methyl acetate
33. What substances does sodium acetate react with?
a) hydrochloric acid +
b) sodium hydroxide when heated +
c) carbonic acid
34. When ethanol and carbon monoxide (P) interact under appropriate conditions, what happens?
a) ethanal
b) propanal
c) propanoic acid +
d) methyl acetate
35. What substances does formic acid react with?
a) copper chloride (P)
b) sodium sulfate
c) potassium bicarbonate +
d) ammonia solution of silver oxide +
36. Unlike stearic acid, oleic acid:
a) liquid at room temperature +
b) soluble in water
c) decolorizes bromine water +
d) reacts with alkalis
37. What substances react with hydrogen?
a) linoleic acid +
b) ethanol
c) propanal +
d) propane
38. What reaction underlies the production of esters?
a) neutralization
b) polymerization
c) esterification +
d) hydrogenation
38. What acid is obtained from the oxidation of isobutyl alcohol:
a) butane +
b) oil
c) valerian
d) 2-methylpropane
39. Acetic acid can't get:
a) oxidation of acetaldehyde
b) reduction of ethanal +
c) oxidation of butanol +
d) methane oxidation
40. Homologues of acetic acid are electrolytes:
a) weak +
b) strong
c) amphoteric
d) all previous answers are incorrect
41. What substances do both phenol and benzene react with?
b) nitrating mixture
c) sodium +
d) aqueous sodium hydroxide solution
42. To detect phenol use:
a) hydrogen chloride
b) freshly prepared solution of copper (II)
c) ferric chloride +
d) bromine water +
43. What is the name of the aldehyde
a) 2-Methyl-3-propylbutanal; b) 2,3-dimethylhexanal; c) 4,5-dimethylhexanal; + d) 2-methyl-2-propylbutanal.
44.
Which substance will ethyl alcohol react with?
a) NaOH; + b) Na; c) CaCO 3; + d) HCl.
45. Arrange the substances in order of increasing acidic properties.
Answer: c, a, b
46. Arrange the substances in order of increasing acidic properties.
Answer: a, c, d
47. What reaction occurs during thermal cracking of petroleum products
a) hydration
b) chlorination
c) breaking the C-C + bond
d) hydrogenation. LITERATURE 1. Shishov S.E., Kalney V.A. School: monitoring the quality of education. - M., 2000. 2.Gorkovenko M.Yu. Lesson developments in chemistry, Moscow "VAKO", 2005. 3. Akhmetov N.S. Textbook for 10th grade educational institutions. M.: Education, 1998. 4. Rudzitis G.E., Feldman R.G. Textbook for 10th grade of secondary school. M.: Education, 1992. 5. Stadnitsky G.V., Rodionov A.I. Ecology: Textbook. manual for universities - 4th ed., corrected. - St. Petersburg: Chemistry, 1997. - 240 pp.: ill. 6. Mazur I.I., Moldavanov O.I. Environmental engineering course: Proc. for universities / Ed. I.I. Mazura.- M.: Higher. school, 1999.- 447 p. 7. Gabrielyan O.S., Ostroumov I.G., Ostroumova E.E. Organic chemistry in tests, tasks, exercises. 10th grade: Educational. manual for educational institutions. – M.: Bustard, 2004. – P. 190–215. 8. Encyclopedia for children. T. 17. Chemistry / Ed. V.A. Volodina. – M.: Avanta+, 2001. – P. 370–393 9. Barkovsky E.V., Vrublevsky A.I. Chemistry tests, Minsk, Unipress, 2002 10. Chemistry: A large reference book for schoolchildren and applicants to universities / E.A. Alferova, N.S. Akhmetov, N.V. Bogomolova et al. M.: Bustard, 1999. 11. Vivyursky V.Ya. Questions, exercises and problems in organic chemistry with answers and solutions. - M.: Humanite. Ed. VADOS Center, 1999. - 688 p. 12. Patapov V.M., Tatarinchik S.N., Averina A.V. Problems and exercises in organic chemistry. - M.: “Chemistry”, 1997. - 144 p.