§xi.3. hydrocarbon derivatives

Hydrocarbon derivatives obtained by replacing one or more hydrogen atoms with an OH group (hydroxy group).

Classification

1. According to the structure of the chain (limiting, non-limiting).

2. By atomicity – monatomic (one OH group), polyatomic (2 or more OH groups).

3. According to the position of the OH group (primary, secondary, tertiary).

Saturated monohydric alcohols

General formula C n H 2 n+1 OH

According to systematic nomenclature (IUPAC), alcohols are named by the hydrocarbons corresponding to the longest chain of carbon atoms with the addition of the ending “ol”,

CH 3 -CH-CH 2 -CH 2 -CH-CH 3 5-methyl-2-hexanol

Numbering starts from the end closest to which the OH group is located.

Isomerism

1. Structural – chain isomerism

isomerism of hydroxy group position

2. Spatial - optical, if all three groups of carbon bonded to the OH group are different, for example:

CH 3 - * C-C 2 H 5

3-methyl-3-hexanol

Receipt

1. Hydrolysis of alkyl halides (see properties of halogen derivatives).

2. Organometallic synthesis (Grignard reactions):

a) primary alcohols are obtained by the action of organometallic compounds on formaldehyde:

CH 3 -MgBr + CH 2 =O CH 3 -CH 2 -O-MgBr CH 3 -CH 2 OH + MgBr (OH)

b) secondary alcohols are obtained by the action of organometallic compounds on other aldehydes:

CH 3 -CH 2 -MgBr+CH 3 -C CH 3 -CH-CH 2 -CH 3

CH 3 -CH-CH 2 -CH 3 +MgBr (OH)

c) tertiary alcohols – by the action of organometallic compounds on ketones:

CH 3 -C-CH 3 + H 3 C-MgBr CH 3 -C-CH 3 CH 3 -C-CH 3 + MgBr (OH)

tert-butyl alcohol

3. Reduction of aldehydes, ketones:

CH 3 -C + H 2 CH 3 -C-OH

CH 3 -C-CH 3 + H 2 CH 3 -CH-CH 3

isopropyl alcohol

4. Hydration of olefins (see properties of olefins)

Electronic and spatial structure

Let's look at the example of methyl alcohol

H-C-O-H 1s 2 2s 2 2p 2 x 2p y 2p z

The angle should be 90 0, in fact it is 110 0 28 /. The reason is the high electronegativity of oxygen, which attracts electron clouds of C-H and O-C orbitals.

Since the hydrogen of the hydroxyl group has its only electron taken away by oxygen, the hydrogen nucleus acquires the ability to be attracted to other electronegative atoms that have lone electrons (oxygen atoms).

Physical properties

C 1 -C 10 are liquids, C 11 and more are solids.

The boiling point of alcohols is significantly higher than that of the corresponding hydrocarbons, halogen derivatives and ethers. This phenomenon is explained by the fact that alcohol molecules are associated through the formation of hydrogen bonds.

:O H…..:O H…..:O H

Associates of 3-8 molecules are formed.

When transitioning to the vapor state, hydrogen bonds are destroyed, which requires additional energy. Because of this, the boiling point increases.

T kip: for primary > for secondary > for tertiary

T pl - vice versa: for tertiary > for secondary > for primary

Solubility. Alcohols dissolve in water, forming hydrogen bonds with water.

C 1 -C 3 – mix indefinitely;

C 4 -C 5 – limited;

higher ones are insoluble in water.

Density alcohols<1.

Spectral characteristics of alcohols

They give characteristic absorption bands in the IR region. 3600 cm -1 (absorbs by a non-associated OH group) and 3200 cm -1 (with the formation of hydrogen bonds - associated OH group).

Chemical properties

They are caused by the presence of the OH group. It determines the most important properties of alcohols. Three groups of chemical transformations involving the OH group can be distinguished.

I. Reactions of hydrogen substitution in the hydroxy group.

1) Formation of alcoholates

a) the effect of alkali metals and some other active metals (Mg, Ca, Al)

C 2 H 5 OH + Na C 2 H 5 ONa + H

sodium ethoxide

Alcoholates are completely decomposed by water to form alcohols and alkalis.

C 2 H 5 Ona + HOH C 2 H 5 OH + NaOH

b) Chugaev-Tserevitinov reaction - the effect of organomagnesium compounds.

C 2 H 5 OH + CH 3 MgBr C 2 H 5 OmgBr + CH 4

The reaction is used in the analysis of alcohols to determine the amount of “mobile hydrogen”. In these reactions, alcohols exhibit very weak acidic properties.

2) Formation of esters on the acid residue – acyl.

a) Esterification reaction – interaction of alcohols with carboxylic acids.

H 2 SO 4 conc

O HCl gas O

CH 3 -C + HO 18 C 2 H 5 H 2 O 16 + CH 3 -C

O 16 H O 18 -C 2 H 5

ethyl acetate

Using the method of labeled atoms, it was established that the esterification reaction is the replacement of an OH group with an alkoxy group. This reaction is reversible, because the resulting water causes hydrolysis of the ester.

b) Acylation of alcohols with acid anhydrides.

CH 3 -C H CH 3 -C

O: + :OC 2 H 5 OH

CH 3 -C OC 2 H 5

acetic anhydride

This reaction is reversible, because When alcohol reacts with anhydride, water is not released (hydrolysis is not possible).

c) acylation of alcohols with acid chlorides

CH 3 -C + HOC 2 H 5 HCl + CH 3 -C-OC 2 H 5

acid chloride

acetic acid

3) Formation of ethers

Ethers are formed by replacing the hydrogen of the oxy group with an alkyl (alkylation of alcohols).

a) alkylation with alkyl halides

C 2 H 5 OH + ClCH 3 HCl + C 2 H 5 OCH 3

b) alkylation with alkyl sulfates or dialkyl sulfates

C 2 H 5 OH + CH 3 O-SO 2 OH C 2 H 5 OCH 3 + H 2 SO 4

C 2 H 5 OH + CH 3 OSO 2 OCH 3 C 2 H 5 OCH 3 + HOSO 2 OCH 3

c) intermolecular dehydration in the presence of a solid catalyst

C 2 H 5 OH + HOC 2 H 5 C 2 H 5 OC 2 H 5 + H 2 O

d) alkylation with isoolefins

CH 3 OH + C-CH 3 CH 3 -O-C-CH 3

CH 3 p,60 0 C CH 3

isobutylene

II. Reactions involving abstraction of an OH group.

1) Replacement of the OH group with Hal.

a) action of HHal;

b) the action of PHal and PHal 5;

c) the effect of SOCl 2 and SO 2 Cl 2 (see methods for obtaining halogen derivatives).

2) dehydration of alcohols (intramolecular elimination of water)

CH 3 -CH-CH-CH 3 H 2 O + CH 3 -CH=C-CH 3

OH CH 3 180 0 C CH 3

3-methyl-2-butanol 2-methyl-2-butene

The abstraction of hydrogen occurs from the least hydrogenated of the 2 neighboring hydroxyl-containing units (Zaitsev’s rule).

III. Oxidation and dehydrogenation of alcohols

The attitude of alcohols towards oxidation is associated with the inductive effect of the C-O bond. The polar C-O bond increases the mobility of hydrogen atoms at the carbon bonded to the OH group.

1) Oxidation of primary alcohols

a) to aldehydes;

CH 3 -C-H + O H 2 O + CH 3 -C + H 2 O

b) to acids

CH 3 -C-H + O + O H 2 O + CH 3 -C

2) Oxidation of secondary alcohols leads to ketones

CH3-C-CH+O H 2 O + CH 3 -C=O

3) Tertiary alcohols do not oxidize under similar conditions, because do not have a mobile carbon atom bonded to the OH group. However, under the influence of strong oxidizing agents (concentrated solutions at high temperatures), the oxidation reaction occurs with the destruction of the carbon chain. In this case, neighboring units (the least hydrogenated ones) are subject to oxidation, because there the inductive effect of the hydroxyl group is more pronounced.

CH 3 -CH 2 -C-CH 3 + O CH 3 -CH-C-CH 3 CH 3 -C-C-CH 3

Alcohols and phenols. Monohydric alcohols.

Test.

1. Alcohol molecules are polar due to the polarity of the hydrogen bond with:

1) oxygen; 2) nitrogen; 3) phosphorus; 4) carbon.

2. Choose the correct statement:

1) alcohols are strong electrolytes; 2) alcohols conduct electricity well;

3) alcohols – non-electrolytes; 4) alcohols are very weak electrolytes.

3. Alcohol molecules are associated due to:

1) formation of intramolecular bonds; 2) formation of oxygen bonds;

3) formation of hydrogen bonds; 4) alcohol molecules are not associated.

4. What type of chemical bond determines the absence of gaseous substances among hydroxy compounds (under normal conditions)?

1) ionic 2) covalent 3) donor-acceptor 4) hydrogen

5. Boiling points of alcohols compared to the boiling points of corresponding hydrocarbons:

1) approximately comparable; 2) below; 3) higher; 4) do not have a clear interdependence.

6. How many primary, secondary and tertiary alcohols are given below?

a) CH3CH2-OH b) C2H5-CH(CH3)-CH2-OH c) (CH3)3C-CH2-OH d) (CH3)3C-OH e) CH3-CH(OH)-C2H5 f) CH3-OH

1) primary - 3, secondary - 1, tertiary - 1 2) primary -2, secondary - 2, tertiary - 2

3) primary - 4, secondary - 1, tertiary - 1 4) primary - 3, secondary - 2, tertiary - 1

7. How many isomeric compounds correspond to the formula C3H8O, how many of them are alkanols?

1) 4 and 3 2) 3 and 3 3) 3 and 2 4) 2 and 2 5) 3 and 1

8. How many isomers belonging to the ether class does 1-butanol have?

1) One 2) Two 3) Three 4) Five

9. What reagent is used to obtain alcohols from haloalkanes?

1) aqueous solution of KOH 2) solution of H2SO4 3) alcohol solution of KOH 4) water

10. What reagent is used to obtain alcohols from alkenes?

1) water 2) hydrogen peroxide 3) weak solution H2SO4 4) bromine solution

11. Ethanol can be obtained from ethylene as a result of the reaction:

1) hydration 2) hydrogenation; 3)halogenation; 4)hydrohalogenation

12. What alcohols are obtained from aldehydes? 1) primary 2) secondary 3) tertiary 4) any

13. Upon hydration of 3-methylpentene-1, the following is formed:

1) 3-methylpentanol-1 2) 3-methylpentanol-3 3) 3-methylpentanol-2 4) pentanol-2

Polyhydric alcohols.

Test.

1. Ethylene glycol does not react with 1)HNO3 2)NaOH 3)CH3COOH 4)Cu(OH)2

2. Which of the following substances will glycerin react with?

1) HBr 2) HNO3 3) H2 4) H2O 5)Cu(OH) 2 6) Ag2O/NH3

3. Ethanediol can be produced by the reaction

1) 1,2-dichloroethane with an alcoholic alkali solution 2) hydration of acetaldehyde

3) ethylene with a solution of potassium permanganate 4) hydration of ethanol

4. A characteristic reaction for polyhydric alcohols is interaction with

1) H2 2) Cu 3) Ag2O (NH3 solution) 4) Cu(OH)2

5. A bright blue solution is formed when copper (II) hydroxide reacts with

1) ethanol 2) glycerin 3) ethanal 4) toluene

6. Copper(II) hydroxide can be used to detect

1) Al3+ ions 2) ethanol 3) NO3- ions 4) ethylene glycol

7. A freshly prepared precipitate of Cu(OH)2 will dissolve if you add

1) propanediol-1,2 2) propanol-1 3) propene 4) propanol-2

8. Glycerol in an aqueous solution can be detected using

1) bleach 2) iron (III) chloride 3) copper (II) hydroxide 4) sodium hydroxide

9. A substance that reacts with Na and Cu(OH)2 is:

1) phenol; 2) monohydric alcohol; 3) polyhydric alcohol 4) alkene

10. Ethanediol-1,2 can react with 1) copper (II) hydroxide 2) iron (II) oxide 3) hydrogen chloride

4) hydrogen 5) potassium 6) phosphorus

11.Aqueous solutions of ethanol and glycerol can be distinguished using:

1) bromine water 2) ammonia solution of silver oxide

4) metallic sodium 3) freshly prepared precipitate of copper (II) hydroxide;

Phenols

Test:

1. The oxygen atom in the phenol molecule forms

1) one σ-bond 2) two σ-bonds 3) one σ-and one π-bond 4) two π-bonds

2. Phenols are stronger acids than aliphatic alcohols because...

1) a strong hydrogen bond is formed between alcohol molecules

2) the phenol molecule contains a larger mass fraction of hydrogen ions

3) in phenols, the electronic system is shifted towards the oxygen atom, which leads to greater mobility of the hydrogen atoms of the benzene ring

4) in phenols, the electron density of the O-H bond decreases due to the interaction of the lone electron pair of the oxygen atom with the benzene ring

3. Choose the correct statement:

1) phenols dissociate to a greater extent than alcohols;

2) phenols exhibit basic properties;

3) phenols and their derivatives do not have a toxic effect;

4) the hydrogen atom in the hydroxyl group of phenol cannot be replaced by a metal cation under the action of bases.

4. Phenol in aqueous solution is

1) strong acid 2) weak acid 3) weak base 4) strong base

5. How many phenols of the composition C7H8O are there? 1) One 2) Four 3) Three 4) two

6. The effect of the benzene ring on the hydroxyl group in the phenol molecule is proven by the reaction of phenol with

1) sodium hydroxide 2) formaldehyde 3) bromine water 4) nitric acid

7. Acid properties are most pronounced in 1) phenol 2) methanol 3) ethanol 4) glycerol

8. Chemical interaction is possible between substances whose formulas are:

1) C6H5OH and NaCl 2) C6H5OH and HCl 3) C6H5OH and NaOH 4) C6H5ONa and NaOH.

9. Phenol reacts with 1) hydrochloric acid 2) ethylene 3) sodium hydroxide 4) methane

10. Phenol does not interact with: 1)HBr 2)Br2 3)HNO3 4)NaOH

11. Phenol does not react with 1) HNO3 2) KOH 3) Br2 4) Cu(OH)2

12. When phenol reacts with sodium,

1) sodium phenolate and water 2) sodium phenolate and hydrogen

3) benzene and sodium hydroxide 4) sodium benzoate and hydrogen

13. A substance that reacts with Na and NaOH, giving a violet color with FeCl3 is:

14. Phenol interacts with solutions

1) Cu(OH)2 2) H2SO4 3) [Ag(NH3)2]OH 4) FeCl3 5) Br2 6) KOH

15. Phenol reacts with

1) oxygen 2) benzene 3) sodium hydroxide

4) hydrogen chloride 5) sodium 6) silicon oxide (IV)

16. You can distinguish phenol from methanol using: 1) sodium; 2) NaOH; 3) Cu(OH)2 4) FeCl3

17. Phenol can be obtained in the reaction

1) dehydration of benzoic acid 2) hydrogenation of benzaldehyde

3) hydration of styrene 4) chlorobenzene with potassium hydroxide

12. Mixed tasks.

1. Interact with each other

1) ethanol and hydrogen 2) acetic acid and chlorine

3) phenol and copper (II) oxide 4) ethylene glycol and sodium chloride

2. A substance that does not react with either Na or NaOH, obtained by intermolecular dehydration of alcohols, is: 1) phenol 2) alcohol 3) ether; 4) alkene

3. A substance that reacts with Na, but does not react with NaOH, and upon dehydration gives an alkene is:

1) phenol; 2) alcohol 3) ether; 4) alkane

4. Substance X can react with phenol, but does not react with ethanol. This substance:

1) Na 2) O2 3) HNO3 4) bromine water

5. In the transformation scheme C6H12O6 → X → C2H5-O-C2H5, substance “X” is

1) C2H5OH 2) C2H5COOH 3) CH3COOH 4) C6H11OH

6. In the transformation scheme ethanol → X → butane, substance X is

1) butanol-1 2) bromoethane 3) ethane 4) ethylene

7. In the transformation scheme propanol-1→ X→ propanol-2, substance X is

1) 2-chloropropane 2) propanoic acid 3) propine 4) propene

Aldehydes.

Test.

1. Which molecule contains 2π bonds and 8 σ bonds: 1) butanedione-2,3 2) propandial 3) pentandial 4) pentanone-3

2. Aldehyde and ketone having the same molecular formula are isomers:

1)position of the functional group; 2) geometric; 3) optical; 4) interclass.

3. The closest homologue for butanal is: 1) 2-methylpropanal; 2) ethanal 3) butanone 4) 2-methylbutanal

4. The minimum number of carbon atoms in the ketone and aromatic aldehyde molecules are equal, respectively:

1)3 and 6; 2)3 and 7; 3)4 and 6; 4)4 and 7.

5. How many aldehydes and ketones correspond to the formula C3H6O? 1) One 2) Two 3) Three 4) Five

6. The interclass isomer for butanal is: 1) 2-methylpropanal; 2) ethanal; 3) butanone 4) 2-methylbutanal

7. The isomer of the carbon skeleton for butanal is: 1) 2-methylpropanal; 2) ethanal; 3) butanone 4) 2-methylbutanal

8. The homologue for propionaldehyde is not: 1) butanal 2) formaldehyde 3) butanol-1 4) 2-methylpropanal

9. The molecule of the substance 2-methylpropen-2-al contains

1) three carbon atoms and one double bond 2) four carbon atoms and one double bond

3) three carbon atoms and two double bonds 4) four carbon atoms and two double bonds

10. As a result of the interaction of acetylene with water in the presence of divalent mercury salts, the following is formed:

1)CH3COH; 2)C2H5OH; 3)C2H4; 4)CH3COOH.

11. The interaction of propyne and water produces: 1) aldehyde 2) ketone 3) alcohol 4) carboxylic acid

12.Acetaldehyde can be obtained by oxidation... 1) acetic acid 2) acetic anhydride 3) acetate fiber 4) ethanol

13. You can obtain aldehyde from primary alcohol using oxidation: 1) KMnO4; 2) O2; 3) CuO 4) Cl2

14. By passing 1-propanol vapor through a hot copper mesh you can get:

1) propanal 2) propanone 3) propene 4) propionic acid

15. Acetaldehyde cannot be obtained in the reaction: 1) dehydrogenation of ethanol 2) hydration of acetylene

3) dehydration of acetic acid 4) 1,1-dichloroethane with an alcoholic alkali solution

16. Pentanal cannot be obtained from: 1) pentanol-1 2) pentine-1 3) 1,1-dichloropentane 4) 1,1-dibromopentane

17. The oxidation of aldehydes produces: 1) carboxylic acids 2) ketones 3) primary alcohols 4) secondary alcohols

18. When aldehydes are reduced, the following are formed: 1) carboxylic acids 2) ketones 3) primary alcohols 4) secondary alcohols

19. Aldehyde cannot be oxidized with: 1) KMnO4 2) CuO 3) OH 4) Cu(OH)2

20. When acetaldehyde reacts with copper (II) hydroxide, it forms

1) ethyl acetate 2) acetic acid 3) ethyl alcohol 4) copper (II) ethoxide

21. What substance is formed during the oxidation of propanal?

1) propanol 2) propyl ester of acetic acid 3) propionic acid 4) methyl ethyl ether

22. During the “silver mirror” reaction, ethanal is oxidized by

1) C-H bonds 2) C-C bonds 3) C=O bonds 4) hydrocarbon radical

23. Formic aldehyde reacts with each of the substances 1) H2 and C2H6 2) Br2 and FeCl3 3) Cu(OH)2 and O2 4) CO2 and H2O

24. Acetaldehyde reacts with each of two substances

1) H2 and Cu(OH)2 2) Br2 and Ag 3) Cu(OH)2 and HCl 4) O2 and CO2

25. Acetaldehyde reacts with each of two substances

1) ammonia solution of silver(I) oxide and oxygen 2) sodium hydroxide and hydrogen

3) copper (II) hydroxide and calcium oxide 4) hydrochloric acid and silver

26. Which reaction equation most accurately describes the “silver mirror” reaction?

1) RCHO + [O] → RCOOH 2) RCHO + Ag2O → RCOOH + 2Ag

3) 5RCHO + 2КМnО4 + 3Н2SO4 → 5RСООН + К2SO4 + + 2МnSO4 + 3Н2О

4) RCHO + 2[Ag(NH3)2]OH → RCHOONH4 + 2Ag + 3NH3 + H2O

27. A qualitative reaction to aldehydes is interaction with: 1) FeCl3 2) Cu(OH) 2 (t) 3) Na 4) NaHCO3

28. A qualitative reaction to formaldehyde is its interaction with

1) hydrogen 2) bromine water 3) hydrogen chloride 4) ammonia solution of silver oxide

29. Formaldehyde interacts with 1) N2 2) HNO3 3) Cu(OH)2 4) Ag(NH3)2OH 5) FeCl3 6) CH3COOH

30. Acetaldehyde interacts with substances: 1) benzene 2) hydrogen 3) nitrogen 4) copper (II) hydroxide 5) methanol 6) propane

31. Propionic aldehyde interacts with substances:

1) chlorine 2) water 3) toluene 4) silver oxide (NH3 solution) 5) methane 6) magnesium oxide

Ketones

32. What is the oxidation state of the carbon atom of the carbonyl group in ketones?

1)0 2) +2 3) -2 4) It depends on the composition of the ketone

33. Dimethylketone is: 1) ethanal; 2) propanal; 3) propanone-1 4) acetone.

34. When ketones are reduced, the following are formed:

1) carboxylic acids 2) primary alcohols 3) secondary alcohols 4) aldehydes

35. The following will not interact with an ammonia solution of silver oxide:

1) butanal 2) formic acid; 3) propine

36. Select the incorrect statement:

1) the carbonyl group of ketones is less polar than in aldehydes;

2) lower ketones are poor solvents;

3) ketones are more difficult to oxidize than aldehydes;

4) ketones are more difficult to reduce than aldehydes.

37. Acetone can be distinguished from its isomeric aldehyde using

1) addition reaction of HCN, 2) hydrogenation reaction 3) indicator 4) reaction with Cu(OH)2.

38. React with hydrogen (in the presence of a catalyst)

1) ethylene 2) acetaldehyde 3) ethanol 4) ethane 5) acetic acid 6) acetone

Carboxylic acids.

Test.

1. The 2-hydroxypropanoic (lactic) acid molecule contains

1) three carbon atoms and three oxygen atoms 2) three carbon atoms and two oxygen atoms

3) four carbon atoms and three oxygen atoms 4) four carbon atoms and two oxygen atoms

2. The weakest acidic properties are exhibited by 1) HCOOH 2) CH3OH 3) CH3COOH 4) C6H5OH

3. Indicate the strongest of the listed carboxylic acids.

1) CH3COOH 2) H2N-CH2COOH 3) Cl-CH2COOH 4) CF3COOH

4. Choose the correct statement:

1) carboxylic acids do not interact with halogens;

2) in carboxylic acids there is no polarization of the O–H bond;

3) halogenated carboxylic acids are inferior in strength to their non-halogenated analogues;

4) halogenated carboxylic acids are stronger than the corresponding carboxylic acids.

Properties

5. Carboxylic acids, interacting with metal oxides and hydroxides, form:

1) salt; 2) indifferent oxides; 3) acid oxides; 4) basic oxides.

6. Acetic acid does not interact with 1) CuO 2) Cu(OH)2 3) Na2CO3 4) Na2SO4

7. Acetic acid can react with 1) potassium carbonate 2) formic acid 3) silver 4) sulfur (IV) oxide

8.Each of two substances interacts with acetic acid:

1) NaOH and CO2 2) NaOH and Na2CO3 3) C2H4 and C2H5OH 4) CO and C2H5OH

9.Formic acid interacts with 1) sodium chloride; 2) sodium hydrogen sulfate;

3) ammonia solution of silver oxide; 4) nitric oxide (II)

10. Formic acid reacts with..., but acetic acid does not.

1) sodium bicarbonate 2) KOH 3) chlorine water 4) CaCO3

11. The following interact with formic acid: 1) Na2CO3 2) HCl 3) [Ag(NH3)2]OH 4) Br2 (p-p) 5) CuSO4 6) Cu(OH)2

12. Propionic acid reacts with 1) potassium hydroxide 2) bromine water 3) acetic acid

4) propanol-1 5) silver 6) magnesium

13. Unlike phenol, acetic acid reacts with: 1) Na 2) NaOH 3) NaHCO3 4) HBr

14.An acid will react with hydrogen, bromine and hydrogen bromide:

1) acetic 2) propionic 3) stearic 4) oleic

15. In the transformation scheme toluene → X → sodium benzoate, compound “X” is

1) benzene 2) benzoic acid 3) phenol 4) benzaldehyde

Receipt

16. Acetic acid can be obtained in the reaction of: 1) sodium acetate with conc. sulfuric acid

2) hydration of acetaldehyde 3) chloroethane and an alcoholic solution of alkali 4) ethyl acetate and an aqueous solution of alkali.

17. Propanic acid is formed as a result of the interaction of: 1) propane with sulfuric acid 2) propene with water

3) propanal with copper (II) hydroxide 4) propanol-1 with sodium hydroxide

18. Pentanic acid is formed as a result of the interaction of: 1) pentane with sulfuric acid 2) pentene-1 with water

3) pentanol-1 with sodium hydroxide 4) pentanal with an ammonia solution of silver oxide

Industrial processes. Oil and products of its processing.

1. A method of processing oil and petroleum products in which chemical reactions do not occur is

1) distillation 2) cracking 3) reforming 4) pyrolysis

2. The apparatus for separating liquid production products is

1) absorption tower 2) distillation column 3) heat exchanger 4) drying tower

3. The basis of primary oil refining is

1) oil cracking 2) oil distillation 3) dehydrocyclization of hydrocarbons 4) reforming of hydrocarbons

4. Choose a synonym for the term “rectification”: 1) reforming; 2) fractional distillation; 3) flavoring; 4) isomerization.

5. The process of decomposition of petroleum hydrocarbons into more volatile substances is called

1) cracking 2) dehydrogenation 3) hydrogenation 4) dehydration

6. Cracking of petroleum products is a method

1) obtaining lower hydrocarbons from higher ones 2) separating oil into fractions

3) obtaining higher hydrocarbons from lower ones 4) aromatization of hydrocarbons

7. The process leading to an increase in the proportion of aromatic hydrocarbons in gasoline is called

1) cracking 2) reforming 3) hydrotreating 4) rectification

8. When reforming, methylcyclopentane as a result of isomerization and dehydrogenation reactions turns into

1) ethylcyclopentane 2) hexane 3) benzene 4) pentene

9. Unsaturated hydrocarbons are obtained by 1) rectification 2) hydrogenation 3) cracking 4) polymerization

10. Straight-run gasoline and cracked gasoline can be distinguished using

1) alkali solution 2) lime water 3) bromine water 4) javel water

11. The composition of fuel oil - the heavy fraction of oil distillation - does not include 1) tar 2) kerosene 3) paraffin 4) oils

When one or more hydrogen atoms in hydrocarbons are replaced by other atoms or groups of atoms, called functional groups, hydrocarbon derivatives are obtained: halogen derivatives, alcohols, aldehydes, ketones, acids, etc. The introduction of a particular functional group into the composition of a compound, as a rule, , radically changes its properties. For example, the introduction of a carboxy group leads to the appearance of acidic properties in organic compounds. The abbreviated formula of hydrocarbon derivatives can be written in the form where is the hydrocarbon residue (radical), Ф is the functional

group. For example, a carboxylic acid can be represented in general form by the formula

Halogen derivatives of hydrocarbons.

The formula of a halogenated hydrocarbon can be represented as where is halogen; - number of halogen atoms. Due to the polarity of the halogen-carbon bond, halogen is relatively easily replaced by other atoms or functional groups, therefore halogen derivatives of hydrocarbons are widely used in organic synthesis. The strength of the carbon-halogen bond increases from iodine to fluorine, so fluorocarbons have high chemical stability. Halogen derivatives of hydrocarbons are widely used in technology. Thus, many of them (dichloromethane, carbon tetrachloride, dichloroethane, etc.) are used as solvents.

Due to the high heat of evaporation, non-flammability, non-toxicity and chemical inertness, fluorocarbons and mixed halogen derivatives have found use as working fluids in refrigeration devices - freons (freons), for example: (freon 12), (freon 22), (freon 114). are also used in extinguishing fires.In connection with the massive use of refrigerants (freons), the problem has arisen of preventing their harmful effects on the environment, since when the refrigerants evaporate, they decompose and the interaction of halogens, especially fluorine, with the ozone layer occurs.

Halogen derivatives of saturated hydrocarbons, for example, serve as starting monomers for the production of valuable polymers (polyvinyl chloride, fluoroplastic).

Alcohols and phenols.

Alcohols are derivatives of hydrocarbons in which one or more hydrogen atoms are replaced by hydroxide groups. Depending on the hydrocarbons, alcohols are divided into saturated and unsaturated; based on the number of hydroxide groups in the compound, monohydric (for example, and polyhydric (for example, glycerol) alcohols are distinguished. Depending on the number of carbon atoms connected to the carbon atom at which the hydroxide group is located, they are distinguished primary

secondary and tertiary alcohols.

The name of alcohols is obtained by adding a suffix to the name of the hydrocarbon (or -diol, triol, etc. in the case of polyhydric alcohols), as well as indicating the number of the carbon atom on which the hydroxide group is located, for example:

Due to the polarity of the oxygen-hydrogen bond, alcohol molecules are polar. Lower alcohols are highly soluble in water, however, as the number of carbon atoms in the hydrocarbon radical increases, the influence of the hydroxide group on the properties decreases and the solubility of alcohols in water decreases. Alcohol molecules are associated due to the formation of hydrogen bonds between them, therefore their boiling points are higher than the boiling points of the corresponding hydrocarbons.

Alcohols are amphoteric compounds; when exposed to alkali metals, easily hydrolyzed alcoholates are formed:

When interacting with hydrohalic acids, the formation of halogenated hydrocarbons and water occurs:

However, alcohols are very weak electrolytes.

The simplest of saturated alcohols is methanol, which is obtained from carbon monoxide and hydrogen under pressure at elevated temperatures in the presence of a catalyst:

Considering the relative simplicity of methanol synthesis and the possibility of obtaining starting reagents from coal, some scientists suggest that methanol will find wider application in technology in the future, including in transport energy. A mixture of methanol and gasoline can be effectively used in internal combustion engines. The disadvantage of methanol is its high toxicity.

Ethanol is produced by fermentation of carbohydrates (sugar or starch):

The starting raw materials in this case are either food products or cellulose, which is converted into glucose by hydrolysis. In recent years, the method of catalytic hydration of ethylene has become increasingly used:

Using the method of cellulose hydrolysis and ethylene hydration allows saving food raw materials. Although ethanol is one of the least toxic alcohols, it causes significant death.

more people than from any other chemical.

When the hydrogen of the aromatic ring is replaced by a hydroxide group, phenol is formed. Under the influence of the benzene ring, the polarity of the oxygen-hydrogen bond increases, so phenols dissociate to a greater extent than alcohols and exhibit acidic properties. The hydrogen atom in the hydroxide group of phenol can be replaced by a metal cation under the influence of a base:

Phenol is widely used in industry, in particular, it serves as a raw material for the production of phenol-formaldehyde polymers.

Aldehydes and ketones.

By oxidation and catalytic dehydrogenation of alcohols, aldehydes and ketones can be obtained - compounds containing a carbonyl group

As you can see, the oxidation or dehydrogenation of a primary alcohol produces an aldehyde, while that of a secondary alcohol produces a ketone. The carbon atom of the carbonyl group of aldehydes is bonded to one hydrogen atom and one carbon atom (radical). The carbon atom of the carbonyl group of ketones is bonded to two carbon atoms (with two radicals).

The names of aldehydes and ketones are derived from the names of hydrocarbons, adding the suffixes -al in the case of an aldehyde and -one in the case of a ketone, for example:

The oxygen-carbon bond of the carbonyl group of aldehydes is highly polarized, so aldehydes are characterized by high reactivity, they are good reducing agents, and easily undergo substitution, addition, condensation and polymerization reactions. The simplest aldehyde - methanal (formaldehyde or formic aldehyde) is prone to

spontaneous polymerization. It is used to produce phenol-formaldehyde and urea-formaldehyde resins and polyformaldehyde.

Ketones are less reactive than aldehydes because the carbonyl group is less polar. Therefore, they are more difficult to oxidize, reduce and polymerize. Many ketones, particularly acetone, are good solvents.

Carboxylic acids.

In carboxylic acids, the functional group is the carboxyl group -COOH. Depending on the number of carboxyl groups in the acid molecule, they are divided into mono-, di- and polybasic, and depending on the radical associated with the carboxyl group - into aliphatic (saturated and unsaturated), aromatic, alicyclic and heterocyclic. According to systematic nomenclature, the names of acids are derived from the name of the hydrocarbon, adding the ending -ova and the word acid, for example, butanoic acid.

However, trivial names that have developed historically are often used, for example:

Acids are usually obtained by oxidation of aldehydes. For example, by hydrating acetylene followed by oxidation of the resulting acetaldehyde, acetic acid is obtained:

Recently, a method for the production of acetic acid was proposed, based on the reaction of methanol with carbon monoxide in the presence of a rhodium catalyst

The acidic properties of the carboxyl group are due to the removal of a proton during the electrolytic dissociation of acids. Proton abstraction is associated with significant polarization of the O-H bond, caused by a shift in electron density from the carbon atom to the oxygen atom of the carboxyl group

All carboxylic acids are weak electrolytes and behave chemically like inorganic weak acids. They react with metal oxides and hydroxides to form salts.

One of the features of carboxylic acids is their interaction with halogen, leading to the formation of halogen-substituted carboxylic acids. Due to the presence of halogens in the acid molecule, polarization of the O-H bond occurs, therefore halogen-substituted acids are stronger than the original carboxylic acids. Acids form esters with alcohols

Or Amines, like ammonia, exhibit basic properties.

When interacting with acids they form salts

Amines are the starting materials for the production of dyes, high molecular weight and other compounds.

Municipal educational institution "Lyceum No. 47" Saratov

Nikitina Nadezhda Nikolaevna – chemistry teacher

PREPARATION FOR THE Unified State Exam (grades 10,11)

Test on the topic: “Monohydric alcohols -

classification, nomenclature, isomerism, physical and chemical properties »

1 . The substance pentanol-2 belongs to:

1) primary alcohols, 2) secondary alcohols; 3) tertiary alcohols; 4) dihydric alcohols.

2. Limiting monohydric alcohol is not:

1) methanol 2) 3-ethylpentanol-13)2-phenylbutanol-1 4) ethanol

3. How many isomeric compounds correspond to formula C 3 H 8 O how many of them belong to alkanols?

1) 4 and 3 2) 3 and 3 3) 3 and 2 4) 2 and 2

4. How many isomers belonging to the ether class does 1-butanol have?

1) One 2) Two 3) Three 4) Five

5. The isomer of the position of the functional group for pentanol-2 is:

1) pentanol-1 2) 2-methylbutanol-2 3) butanol-2 4) 3-methylpentanol-1

6. How many primary, secondary and tertiary alcohols are given below?

1) CH 3 CH 2 -OH 2) C 2 H 5 -CH(CH 3 )-CH 2 -OH 3) (CH 3 ) 3 C-CH 2 -OH

4) (CH 3 ) 3 C-OH e) CH 3 -CH(OH)-C 2 H 5 f) CH 3 -OH

1) primary - 3, secondary - 1, tertiary - 1 2) primary - 2, secondary - 2, tertiary - 2
3) primary - 4, secondary - 1, tertiary - 1 4) primary - 3, secondary - 2, tertiary - 1

7. What type of chemical bond determines the absence of gaseous substances among hydroxy compounds (under normal conditions)?

1) ionic 2) covalent 3) donor-acceptor 4) hydrogen

8. Boiling points of alcohols compared to the boiling points of corresponding hydrocarbons:

1) approximately comparable; 2) below; 3) higher; 4) do not have a clear interdependence.

9. Alcohol molecules are polar due to the polarity of the hydrogen bond with:

1) oxygen; 2) nitrogen; 3) phosphorus; 4) carbon.

10. Choose the correct statement:

1) alcohols are strong electrolytes; 2) alcohols conduct electricity well;

3) alcohols – non-electrolytes; 4) alcohols are very weak electrolytes.

11. Alcohol molecules are associated due to:

1) formation of intramolecular bonds; 2) formation of oxygen bonds;

3) formation of hydrogen bonds; 4) alcohol molecules are not associated.

12. Methanol does not interact with :

1) K 2) Ag 3) CuO 4) O 2

13. Ethanol does not interact with :

1) NaOH 2) Na 3) HCl 4) O 2

14. Which of the following substances does ethanol not interact with:

1) Na 2) NaOH 3) HBr 4) O 2

15. Propanol does not interact with:

1) Hg 2) O 2 3) HC l 4) K

16. Ethanol does not react with:

1) Na 2) CuO 3) HCOOH 4) CuSO 4

17.. Saturated monohydric alcohols are characterized by interaction with:

1) KOH (solution) 2) K 3) Cu(OH) 2 4) Cu

18. When oxidizing primary butyl alcohol, we get:

1) propanal; 2) butyraldehyde; 3) ethanal; 4) methanal.

19. When oxidizing (dehydrogenating) a secondary alcohol, the following is obtained:

1) tertiary alcohol 2) aldehyde 3) ketone 4) carboxylic acid.

20. Which of the hydroxyl-containing substances turns into a ketone during dehydrogenation?:

1) methanol 2) ethanol 3) propanol-2 4) o-cresol.

21. The oxidation of butanol-1 produces:

1) ketone 2) aldehyde 3) acid 4) alkene

22. The oxidation of methanol produces:

1) methane 2) acetic acid 3) methanal 4) chloromethane

23. The oxidation of propanol-2 produces:

1) aldehyde 2) ketone 3) alkane 4) alkene

24. When methanol is heated with oxygen on a copper catalyst, the following is formed:

1) formaldehyde 2) acetaldehyde 3) methane 4) dimethyl ether

25. When ethanol is heated with oxygen on a copper catalyst, the following is formed:

1) ethene 2) acetaldehyde 3) diethyl ether 4) ethanediol

26. One of the products of the reaction that occurs when methanol is heated with concentrated. sulfuric acid, is:

1) CH 2 =CH 2 2)CH 3 -O-CH 3 3) CH 3 Cl 4) CH 4

27. During intramolecular dehydration of butanol-1, the following is formed:

1) butene-1 2) butene-2 ​​3) dibutyl ether 4) butanal.

28. Intramolecular dehydration of alcohols leads to the formation of:

1) aldehydes 2) alkanes 3) alkenes 4) alkynes

29. What substance is formed when ethyl alcohol is heated to 140 O C in the presence of concentrated sulfuric acid?
1) acetaldehyde 2) dimethyl ether 3) diethyl ether 4) ethylene

30. The acidic properties of ethanol are manifested in the reaction with

1) sodium 2) copper (II) oxide

3) hydrogen chloride 4) acidified solution of potassium permanganate

31. Which reaction indicates the weak acidic properties of alcohols:

1) with Na 2) with NaOH 3) with NaHCO 3 4) with CaO

32. Alcoholates are obtained from alcohols when they interact with:

1) KMnO4; 2) O 2 3) CuO 4) Na

33. When propanol-1 reacts with sodium, the following is formed:

1) propene; 2) sodium propylate 3) sodium ethoxide 4) propanediol-1,2

34. When alcohols are exposed to alkali metals, the following are formed:

1) easily hydrolyzed carbonates; 2) carbonates that are difficult to hydrolyze;

3) difficult to hydrolyze alcoholates; 4) easily hydrolyzed alcoholates.

35.What substance is formed in the reaction of pentanol-1 with potassium?

1) C 5 H 12 OK; 2) C 5 H 11 OK; 3) C 6 H 11 OK; 4) C 6 H 12 OK.

36. Substance that reacts withNa , but not responsive withNaOH , upon dehydration giving an alkene is:

1) phenol; 2) alcohol 3) ether; 4) alkane

37. Which of the following alcohols reacts most actively with sodium?

1) CH 3 CH 2 OH 2) CF 3 CH 2 OH 3) CH 3 CH(OH)CH 3 4) (CH 3 ) 3 C-OH

38. What is the molecular formula of the product of the reaction of pentanol-1 with hydrogen bromide?

1) C 6 H 11 Br; 2) C 5 H 12 Br; 3) C 5 H 11 Br; 4) C 6 H 12 Br.

39. During the reaction of ethanol with hydrochloric acid in the presence of H 2 SO 4,

1) ethylene 2) chloroethane 3) 1,2-dichloroethane 4) vinyl chloride

40. Butane can be obtained from ethanol by sequential action

1) hydrogen bromide, sodium 2) bromine (irradiation), sodium

3) concentrated sulfuric acid (t> 140°), hydrogen (catalyst, t°)

4) hydrogen bromide, alcohol solution of sodium hydroxide

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