Cycloalkanes: Building, receipt and chemical properties. The lesson "Arena and their classification" Reaction of accession to cycloalkanes
Physical properties
Benzole and its nearest homologues are colorless liquids with a specific smell. Aromatic hydrocarbons are lighter than water and do not dissolve in it, but it is easily dissolved in organic solvents - alcohol, ether, acetone.
Benzole and his homologs themselves are good solvents for many organic substances. All the arenas are burning with a smoking flame due to the high carbon content of the VIK molecules.
The physical properties of some arena are presented in the table.
Table. Physical properties of some arena
|
Name |
Formula |
t °. drop, |
t ° .kip., |
|
Benzene |
C 6 H 6 |
5,5 |
80,1 |
|
Toluene (methylbenzene) |
C 6 H 5 СH 3 |
95,0 |
110,6 |
|
Ethylbenzene |
C 6 H 5 C 2 H 5 |
95,0 |
136,2 |
|
Xylene (dimethylbenzene) |
C 6 H 4 (SH 3) 2 |
||
|
ortho- |
25,18 |
144,41 |
|
|
meta- |
47,87 |
139,10 |
|
|
couple- |
13,26 |
138,35 |
|
|
Propillbenzene. |
From 6 N 5 (CH 2) 2 CH 3 |
99,0 |
159,20 |
|
Kumol (IsopropylBenzene) |
C 6 H 5 CH (CH 3) 2 |
96,0 |
152,39 |
|
Styrene (VinylBenzene) |
C 6 H 5 CH \u003d CH 2 |
30,6 |
145,2 |
Benzene - light-boiling ( t. kip\u003d 80.1 ° C), colorless liquid, does not dissolve in water
Attention! Benzene - poison, acts on the kidneys, changes the blood formula (with long-term exposure), may violate the structure of chromosomes.
Most aromatic hydrocarbons are dangerous for life, toxic.
Receiving arena (benzene and his homologues)
In the laboratory
1. Flooring of benzoic acid salts with solid alkalis
C 6 H 5 -Coona + NaOH T →C 6 H 6 + Na 2 CO 3
sodium benzoate
2. Nureza Fitting Reaction: (here g - halogen)
With 6.H. 5 -G + 2.Na. + R.-G →C. 6 H. 5 - R. + 2 Na.G.
FROM 6 H 5 -Cl + 2NA + CH 3 -CL → C 6 H 5 -CH 3 + 2NACL
In industry
- isolated from oil and coal by the method of fractional distillation, reforming;
- from coiling resin and coke gas
1. Alkanov dehydrocyclication With the number of carbon atoms more than 6:
C 6 H 14 T. , Kat.→ C 6 H 6 + 4H 2
2. Trimmerization of acetylene (only for benzene) - r. Zelinsky:
3C 2. H 2. 600 ° C. , Act. coal → C 6 H 6
3. Dehydrization Cyclohexane and his homologues:
Soviet academician Nikolai Dmitrievich Zelinsky found that benzene is formed from cyclohexane (cycloalkan dehydrogenation
C 6 H 12 T, Kat.→ C 6 H 6 + 3H 2
C 6 H 11 -CH 3 T. , Kat.→ C 6 H 5 -CH 3 + 3H 2
methylcyclohexantoluole
4. Alkylation of benzene. (Obtaining Gomologists Benzene) - R Freidel Korflas.
C 6 H 6 + C 2 H 5 -CL T, AlCl3.→ C 6 H 5 -C 2 H 5 + HCl
chlorhetan ethylbenzene
Chemical properties arenaments
I.. Oxidation reactions
1. Burning (smoking flame):
2C 6 H 6 + 15O 2 T. → 12CO 2 + 6H 2 O + Q
2. Benzene under normal conditions does not discolor bromine water and water solution Manganese
3. Benzol homologs are oxidized by potassium permanganate (discolored by manganese):
A) in an acidic medium to benzoic acid
Under action on gomologists of potassium permanganate and other strong oxidants, side chains are oxidized. No matter how difficult the chain of the substituent, it is destroyed, with the exception of A -Atoma carbon, which is oxidized in the carboxyl group.
Gomezol homologs with one side chain give benzoic acid:
Homologists containing two side chains give two-axis acids:
5C 6 H 5 -C 2 H 5 + 12KMNO 4 + 18H 2 SO 4 → 5C 6 H 5 COOH + 5CO 2 + 6K 2 SO 4 + 12MNSO 4 + 28H 2 O
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
Simplified :
C 6 H 5 -CH 3 + 3O KMNO4.→ C 6 H 5 COOH + H 2 O
B) in neutral and low-alkaline to benzoic acid salts
C 6 H 5 -CH 3 + 2KMNO 4 → C 6 H 5 COOK + K he + 2mno 2 + H 2 O
II.. Reaction of joining (harder than alkenes)
1. Halogenation
C 6 H 6 + 3Cl 2 H. ν → C 6 H 6 Cl 6 (Hexakhlorcyclohexane - Hexakhloran)
2. Hydrogenation
C 6 H 6 + 3H 2 T. , Pt. or Ni. → C 6 H 12 (cyclohexane)
3. Polymerization
III. Reactions of substitution - ion mechanism (lighter than alkanov)
b) benzene homologues during irradiation or heating
By chemical properties, alkyl radicals are similar to alkanes. The hydrogen atoms in them are replaced by halogen in a free-radical mechanism. Therefore, in the absence of a catalyst, during heating or UV irradiation, a radical reaction of substitution in the side chain is underway. The effect of a benzene ring on alkyl substituents leads to the fact that there is always a hydrogen atom at the carbon atom, directly related to the benzene ring (A -Atoma carbon).
1) C 6 H 5 -CH 3 + CL 2 H. ν → C 6 H 5 -CH 2 -CL + HCl
c) Benzene homologues in the presence of a catalyst
C 6 H 5 -CH 3 + CL 2 Alcl 3 → (a mixture of orta, a pair of derivatives) + HCl
2. Nutration (with nitric acid)
C 6 H 6 + HO-NO 2 T, H2SO4→ C 6 H 5 -NO 2 + H 2 O
nitrobenzene - smell almond!
C 6 H 5 -CH 3 + 3HO-NO 2 T, H2SO4→ FROM H 3 -C 6 H 2 (NO 2) 3 + 3H 2 O2,4,6-trinitrotroluole (Tol, Trotil)
The use of benzene and his homologues
Benzene C 6 H 6 is a good solvent. Benzole as an additive improves the quality of motor fuel. Serves as raw materials to obtain many aromatic organic compounds - nitrobenzene C 6 H 5 NO 2 (solvent, aniline is obtained from it), chlorobenzene C 6 H 5 Cl, phenol C 6 H 5 OH, styrene, etc.
Toluene C 6 H 5 -CH 3 is a solvent, used in the production of dyes, medicinal and explosives (TROTIL (TOL), or 2,4,6-trinitrotrol tilt).
XyleneC 6 H 4 (CH 3) 2. Technical xylene - a mixture of three isomers ( ortho-, meta- I. couple-xilolov) - used as a solvent and source product for the synthesis of many organic compounds.
IsopropylBenzene. C 6 H 5 -CH (CH 3) 2 serves to obtain phenol and acetone.
Chloro derivatives Benzol Used to protect plants. Thus, the substitution product in benzene atoms n atoms chlorine - hexachlorobenzene with 6 CL 6 - fungicide; It is used for dry wheat seed etching and rye against solid head. Product addition of chlorine to benzene - hexachlorcyclohexane (hexachlororan) with 6 H 6 CL 6 - insecticide; It is used to combat harmful insects. These substances relate to pesticides - chemicals to combat microorganisms, plants and animals.
Styrene C 6 H 5 - CH \u003d CH 2 is very easily polymerized, forming polystyrene, and copolymering with butadiene - butadienestrol rubber.
Video experiments
Task number 3.
From the proposed list of connections, select those that contain carbon atoms in SP 3-hybridization. The number of correct answers can be any.
Answer: 345.
Task number 4.
From the proposed connections list, select those that do not contain carbon atoms in SP 3-hybridization. The number of correct answers can be any.
2) Vinilacetylene
3) cyclopropan
5) Ethylbenzene.
Answer: 24.
Task number 6.
From the proposed list of substances, select those that do not react with benzene. The number of correct answers can be any.
1) Bromomopod
3) nitric acid
4) caustic potassium
Answer: 124.
Task number 7.
From the proposed list of substances, select those that react with benzene, but do not react with ethylene. The number of correct answers can be any.
1) Propylene
4) Chlorbutan
5) Nitrate potassium
Answer: 14.
Task number 8.
From the proposed list of substances, select those that do not react with benzene, but react with propylene. The number of correct answers can be any.
2) permanganate potassium
3) bromine water
4) lime water
5) chloroorod
Answer: 235.
Task number 9.
From the proposed list of substances, select those that react with benzene and with cyclohexane. The number of correct answers can be any.
1) hydrogen
3) Oxygen
5) nitric acid
Answer: 345.
Task number 11.
From the proposed list of substances, select those that react with toluene, but do not react with methane. The number of correct answers can be any.
1) Oxygen
2) hydrogen
5) permanganate potassium
Answer: 25.
Task number 12.
From the proposed list of substances, select those that react with toluene and with cyclohexen. The number of correct answers can be any.
2) permanganate potassium
3) hydrogen
4) bromine water
5) 3-phenylpropen
Answer: 23.
Task number 13.
From the proposed list of substances, select those that do not react with toluene, but react with methylcyclopropane. The number of correct answers can be any.
3) hydrogen
4) Bromochement
Answer: 4.
Task number 15.
From the proposed list of substances, select those that do not react with toluene and with isobutane. The number of correct answers can be any.
2) Formaldehyde
5) nitric acid
Answer: 123.
Task number 16.
3) Bromomopod
4) Oxygen
Answer: 135.
Task number 17.
From the proposed list of substances, select those that react with the styrene, but do not react with benzene. The number of correct answers can be any.
1) Permanganate Potassium
2) hydrogen
3) Oxygen
4) caustic natra
5) chloroorod
Answer: 15.
Task number 18.
From the proposed list of substances, select those that react with the styrene, but do not react with the cumol. The number of correct answers can be any.
1) hydrogen
4) Iodovododorod
Answer: 4.
Task №19.
From the proposed list of substances, select those that react with the styrene, but do not react with the ethane. The number of correct answers can be any.
1) nitric acid
3) Bromomopod
4) sodium permanganate
Answer: 345.
Task number 20.
From the proposed list of substances, select those that react with cumol, but do not react with benzene. The number of correct answers can be any.
1) Oxygen
3) permanganate potassium
4) hydrogen
Answer: 3.
Task number 27.
5) 2-methylbutan
Answer: 14.
Task №22.
From the proposed list of substances, select those that react with the acidified solution of potassium permanganate when heated. The number of correct answers can be any.
4) Ethylbenzene.
Answer: 124.
Task number 23.
From the proposed list of substances, select those that do not react with the acidified solution of potassium permanganate when heated. The number of correct answers can be any.
1) 1,2-dimethylbenzene
2) IsopropylBenzene.
3) phenyleten
5) Isobutylene
Answer: 4.
Task number 24.
From the proposed list of substances, select those that discolor the bromine water. The number of correct answers can be any.
1) 2-phenylpropen
2) methylcyclopropan
3) Ethylbenzene.
5) Propylene
Answer: 1245.
Task №25
From the proposed list of substances, select those that do not discolor bromine water. The number of correct answers can be any.
1) 2-methyl-3-phenylpropane
2) 3-phenylpropen
3) IsopropylBenzene.
4) tert-Butulbenzene.
5) VinylBenzene.
Answer: 134.
Task number 26.
From the proposed list of substances, select those that can enter into a radical substitution reaction with bromine. The number of correct answers can be any.
3) 1,4-diethylbenzene
4) phenylmethane
5) Cyclopentane
Answer: 2345.
Task number 27.
From the proposed list of substances, select those that cannot enter into a radical substitution reaction with chlorine. The number of correct answers can be any.
Answer: 35.
Task №28.
2) benzylbromide
4) benzoic acid
5) m.-Bromtoluloole
Answer: 24.
Task number 29.
From the proposed list of substances, select those that can be obtained from benzene into one step. The number of correct answers can be any.
1) benzoic acid
3) Phenylents
4) Cyclopentane
Answer: 235.
Task number 30.
1) Phenylents
3) 1,2-dibrom-1-phenyletan
4) 1-phenylenediol-1,2
5) Butadienestyrene rubber
Answer: 1345.
Task number 31.
From the proposed list of substances, select those that can be obtained from Cumol in one step. The number of correct answers can be any.
1) benzoic acid
3) 2-Brom-2-phenylpropan
4) carbon dioxide
5) Potassium benzoate
Answer: 1345.
Task number 32.
From the proposed list of substances, select those that can be oxidized to benzoic acid. The number of correct answers can be any.
2) Ethylbenzene.
4) 1,3-dimethylbenzene
Answer: 235.
Task number 33.
From the proposed list of substances, select those that can be obtained from ethylbenzene in one step. The number of correct answers can be any.
4) 1-Brom-1-Phenyletan
5) Fur Gas
Answer: 145.
Task number 34.
From the proposed list of substances, select those that can be obtained in one step from toluene. The number of correct answers can be any.
1) benzoic acid
3) Chlorbenzene.
4) p-Nitrotolol
5) 1,4-dimethylbenzene
Answer: 145.
Task number 35.
From the proposed list of substances, select those that can be obtained from styrene in one stage. The number of correct answers can be any.
1) Phenylents
2) 1-Brom-1-Phenyletan
3) 1,1-dibrom-1-phenylethan
4) benzoic acid
5) carbon dioxide
Answer: 1245.
Task number 36.
From the list of the list, select two incorrect statements.
1) Styrene reacts like with bromine waterand hydrogen
2) To obtain cumenes in one stage, benzene and propylene can be used as starting materials.
3) When oxidizing benzene under rigid conditions, benzoic acid can be obtained.
4) in the interaction of propylene and benzene in the presence of a catalyst, the main product is n-propylbenzene.
5) VinylBenzene is used in the production of some types of rubber.
Answer: 34.
Task number 37.
1) carbon atoms in the benzene molecule are located in different states of hybridization of orbital
2) When the styrene is making a hot acidified solution of potassium permanganate, fluid discoloration is observed.
3) Toloque reaction with bromine water leads to instantaneous decolorization of the solution.
4) To obtain kumol, as starting materials, both isopropyl chloride and 1-chloropropane can be used as starting materials.
5) Cumol and styrene are able to polymerize and give copolymers with butadiene.
Answer: 24.
Task number 38.
1) When igniting the sample of benzene in air, carbon dioxide and water are formed.
2) To obtain phenylmethane in one stage, methane and chlorobenzene can be used in the presence of aluminum chloride.
3) The interaction of ethylbenzene with a hot acidified solution of potassium permanganate leads to the formation of phenyletanic acid.
4) upon receipt of toluene by the method of catalytic reforming as starting materials can be taken n.-Heptan and methylcyclohexane.
5) benzene, toluene and ethylbenzene can interact both with bromine in the presence of iron and with a thread mixture.
Answer: 23.
Task number 39.
From the list of the list, select 2 correct allegations.
1) Kumol, toluene and styrene are described by the general formula C n h 2 n -6.
2) when hydrogenating benzene and toluene in rigid conditions are formed, respectively, mainly n.-Hexan I. n.-heptane.
3) Toluene and ethylbenzene can enter into a radical substitution reaction with chlorine and bromine into the light.
4) Styrene and benzene can be oxidized to benzoic acid with a hot acidified solution of potassium permanganate.
5) in the interaction of styrene with a solution of bromine in an organic solvent and water in the presence of sulfuric acid, respectively, 1,2-dibrom-1-phenyletan and 1-phenylethanol are formed.
Answer: 35.
Task number 40.
From the list of the list, select 2 incorrect allegations.
1) both benzene and styrene can hydrogen in the formation of cycloalkanes
2) in the interaction of bromomethane with benzene in the presence of aluminum chloride, you can get toluene
3) The interaction of benzene with a thread mixture can lead to a mixture of nitrobenzene and 1,4-dinitrobenzene
4) the interaction of benzoic acid with a thread mixture leads mainly to education m.-Nitrobenzoic acid
5) In the bromination of toluene in the presence of iron, a mixture is formed, consisting mainly of 2- and 3-bromotololool
Answer: 35.
Task number 41.
What judgments about the properties of aromatic hydrocarbons are faithful? The number of correct answers can be any.
1) Data of hydrocarbons under certain conditions react with ethylene and ethane.
2) benzene, toluene and styrene relative to each other are homologists.
3) Styrene and ethylbenzene can be converted into benzoic acid in one stage.
4) The benzene molecule is flat and contains a conjugate system that includes 4 π-bonds.
5) Benzole can be obtained in one stage of n-hexane and potassium benzoate.
Answer: 35.
Task number 42.
What judgments about the properties of benzene are not faithful? The number of correct answers can be any.
1) the nitration of benzene is carried out under the action of concentrated nitric acid in the presence of mercury cation.
2) Aluminum chloride can be used for chloride and bromination of benzene as a catalyst.
3) When the benzene is oxidized by a hot neutral solution, potassium benzoate is formed by potassium permanganate.
4) benzene hydrogenation can lead to education n.-Gexana or cyclohexane, depending on the reaction conditions.
5) The alkylation of benzene can be carried out using alkenes and halolens as reagents.
Answer: 134.
Task number 43.
What judgments about the properties of toluene are faithful? The number of correct answers can be any.
1) Toluene and ethylbenzene belong to each other as homologues.
2) Toluene can react with both chlorine and chloride.
3) catalytic hydrogenation of toluene leads to 2-methylhexane.
4) From toluene in one stage, benzylbromide and benzoic acid can be obtained.
5) When interacting toluene with water, you can get a benzyl alcohol.
Answer: 14.
Task number 44.
What judgments about the properties of Kumol are faithful? The number of correct answers can be any.
1) Tertiary halogen derivatives are formed when the cumene bromils are formed.
2) Kumol and n.-Butlibenzene are homologists.
3) Cumol can be obtained based on propylene and benzene.
4) When oxidizing the cumol, one organic product is formed under rigid conditions.
5) Cumol and 2-phenylpropane are easers of each other.
Answer: 134.
Task number 45.
What judgments about styrene properties are true? The number of correct answers can be any.
1) Styrene can be included in the rubber
2) Styrene can bleach bromine water and sodium permanganate solution
3) With partial styrene hydrogenation, you can get toluene
4) Styrene and allylbenzene are homologues relative to each other
5) 1-Brom-1-phenyletan and 2-phenyl ethanol can be turned into styrene
Answer: 1245.
Task number 46.
Answer: 432.
Task number 47.
Set the correspondence between the name of the substance and its molecular formula.
Write in the table selected numbers under the appropriate letters.
Answer: 312.
Task number 48.
Set the correspondence between the name of the substance and its molecular formula.
Write in the table selected numbers under the appropriate letters.
Answer: 244.
Task number 49.
Install the correspondence between the name of the substance and the product of its interaction with one equivalent of bromine in the presence of aluminum chloride.
Write in the table selected numbers under the appropriate letters.
Answer: 321.
Task number 50.
Install the correspondence between the name of the substance and the product of its interaction with one equivalent of bromine without catalyst and irradiation.
Write in the table selected numbers under the appropriate letters.
Answer: 424.
Task number 51.
Set the correspondence between the name of the substance and the product of its interaction with one equivalent of chlorine under radical substitution conditions.
Write in the table selected numbers under the appropriate letters.
Answer: 431.
Task number 52.
Set the correspondence between the name of the substance and the aromatic hydrocarbon, which can be obtained from it in one step.
Write in the table selected numbers under the appropriate letters.
Answer: 231.
Task number 53.
Set the match between the pair of substances and the reagent by which they can be distinguished.
Write in the table selected numbers under the appropriate letters.
Answer: 341.
Task number 54.
Install the match between the pair of substances and the reagent with which they both can react.
| SUBSTANCE | REAGENT |
| A) ethylene and styrene |
Cycloalkanes - These are the limit (saturated) hydrocarbons that contain a closed carbon cycle.
General formula Cycloalkanes C n h 2nwhere n≥3..
Building cycloalkanes
Carbon atoms in cycloalkane molecules are in a state of SP 3-hybridization and forms four σ-bonds S-C and C-N. Depending on the size of the cycle, valence angles are changing.
The simplest cycloalkan is cyclopropane, represents, in essence, a flat triangle.
σ-bonds in the cyclopropane call "Banana". They do not lie along the axis connecting the nuclei of atoms, but deviate from it, reducing the voltage in the cyclopropane molecule.
According to the properties of "banana" relations resemble π-communications. They are easily broken.
Therefore, cyclopropane is very easy to enter the connection reaction with the carbon cycle break.
The remaining cycloalkans have a non-planning structure. The cyclobutan molecule has a flection of the line connecting the first and third carbon atoms in the ring:
Cyclobutanealso reacts joining But the angular voltage in cyclobutane is less than in the cyclopropane, so the reaction of joining the cyclobutan proceeds more difficult.
Large cycles have a more complex, non-planning structure, as a result of which the angular stress in the molecules of large cycloalkanes is almost absent.
Cycloalkanes with a large cycle do not enter into the reaction of attachment. They are characterized by reactions of substitution.
The structure of cyclopentane is also not a molecule, the molecule is the so-called "envelope".
The cyclohexane molecule is not a flat polygon and takes various conformations having the name "Armchair" and "Bath":
"Chair" "Bath"
Isomerius cycloalkanes
Structural isomeria
For cycloalkans characteristic structural isomeria,associated S. different number carbon atoms in the ring, different number of carbon atoms in substituents and with the position of substituents in the cycle.
- Isomers with different numbers of carbon atoms in the cycle Different with the size of the carbon cycle.
| Ethylcyclopropan | Methyl cyclobutane |
 |  |
- Isomers with different numbers of carbon atoms in substituentthey are distinguished by the structure of the substituents from the same carbon cycle.
| 1-methyl-2-propylcyclopentan | 1,2-diethylcyclopentan |
 |
- Isomers with different positions of identical substituents in the carbon cycle.
| For example. |
| 1,1-dimethylcyclohexane | 1,2-dimethylcyclohexane |
 |  |
- Interclative isomeria: Cycloalkanes are amomer than alkenes.
| Cyclopropan | Propylene |
 |
Geometric (cis-trans-) isomeria
In cycloalkanes with two substituents, located near the neighboring carbon atoms in the cycle of cis-trans isomeria due to various mutual location in the space of substituents relative to the cycle plane.
| cis-1,2-dimethylcyclopropan | trance-1,2-dimethylcyclopropan |
 |  |
For 1,1-dimethyl cyclopropane cis-trans.-Someteria is not characteristic.
Nomenclature of cycloalkanes
In the names of cycloalkanes, the prefix is \u200b\u200bused.
| Name of cycloalkane | Structural formula |
| Cyclopropan |  |
| Cyclobutane | |
| Cyclopentane |  |
| Cyclohexane |  |
The name of cycloalkanes is based on the following rules:
1. The cycle is taken by g.lavane carbon chain. At the same time, it is believed that hydrocarbon radicals that are not included in the main chain are in it substituents.
2. Numbers carbon atoms in the cycle so that carbon atoms that are connected to substituents received minimum possible numbers. And the numbering should be started with more close to K. senior group The end of the chain.
3. They call all radicals, pointing ahead of the numbers that indicate their location in the main chain.
For the same substituents, these figures indicate a comma, while the number of identical substituents is denoted by consoles di-(two), three- (three), tetra (four), penta (five), etc.
For example, 1,1-dimethylcyclopropane or 1,1,3-trimethylcyclopentane.
4. The names of the substituents with all the prefixes and numbers are in alphabetical order.
For example: 1,1-dimethyl-3-ethylcyclopentan.
5. Call a carbon cycle.
Chemical properties of cycloalkanes
Cycloalkanes with a small cycle (cyclopropane, cyclobutane and their substituted homologues) because of the big tension in the ring can enter into the reaction attachment.
1. Connection reactions to cycloalkanes
1.1. Hydrogenation of cycloalkanes
With hydrogen can react small cycles, as well as (in harsh conditions) cyclopentane. In this case, the rings and the formation of alkane occurs.
Cyclopropane and cyclobutane Pretty easily attach hydrogen when heated in the presence of a catalyst:
Cyclopentane Joins hydrogen in harsh environments:
Bromming proceeds more slow and selectively.
Cyclohexane and cycloalkans with a large number of carbon atoms in a cycle with hydrogen do not react.
1.2. Halogenation of cycloalkanes
Cyclopropane and cyclobutane react with halogens, while the halogen is connected to the molecule, accompanied by a rings of the ring.
1.3. Hydroalogenation
Cyclopropin and its homologs with alkyl substituents in a three-selected cycle Enter with halogen hydrogen in the reaction of joining with a cycle break.
2. Reactions of substitution
2.1. Haloiding
Cyclopentane halogenation, cyclohexane and cycloalkanes with a large number of carbon atoms in the cycle proceeds by mechanism radical substitution.
When chloroing methylcyclopentan, the substitution is preferably flowing in a tertiary carbon atom:
2.2. Nuting cycloalkanes
In the interaction of cycloalkanes with diluted nitric acid, nitrocycloalkanes are formed during heating.
2.3. Dehydrification
When heated cycloalkanes in the presence of catalysts proceeds Dehydrogenation -hydrogen cleavage.
Cyclohexane and its derivatives are dehydrated when heated and under the action of a catalyst to benzene and its derivatives.
3. Oxidation of cycloalkanes
3.1. Combustion
Like all hydrocarbons, alkanes are burning to carbon dioxide and water. Cycloalkanov combustion equation in general form:
C n h 2n + 3N / 2O 2 → NCO 2 + NH 2 O + Q.
2C 5 H 10 + 15O 2 → 10CO 2 + 10H 2 O + Q.
Cycloalkanes (cycloparaffins, naphthenes) - cyclic saturated hydrocarbons, chemical structure Close to alkanes. There are only simple single bond sigma (σ-bonds), do not contain aromatic ties.
Cycloalkans have a greater density and higher melting temperatures, boiling than the corresponding alkanes. The total formula of their homologous series is C n h 2n.
Nomenclature and isomerism of cycloalkanes
The names of cycloalkanes are formed by adding the prefix "Cyclo-" to the name of the alkane with the corresponding number: cyclopropane, cyclobutane, etc.
As with alkanans, the carbon atoms of cycloalkanes are in SP 3 hybridization.
In addition to the isomerism of the carbon skeleton, for cycloalkans is characterized by interclative isomerism with alkens and spatial geometric isomeria in the form of the existence of cis and trans isomers.
Getting cycloalkanes
In industry, cycloalkanes are obtained in several ways:
In the laboratory conditions, cycloalkanes can be obtained by the reaction of the degalogenation of digalogenels.
Chemical properties of cycloalkanes
It is important to note that cyclopropane and cyclobutane reacts in the reaction of the attachment, showing the properties of unsaturated compounds. For cyclopentane and cyclohexane, the attachment reaction is not characteristic, they preferably enter the reaction of substitution.
© Bellevich Yuri Sergeevich 2018-2020
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