Characteristics of the chemical bond of alkanes. Alkanes. Being in nature and receiving

It would be useful to start with a definition of the concept of alkanes. These are saturated or saturated. We can also say that these are carbons in which the connection of C atoms is carried out through simple bonds. The general formula is: CnH₂n+ 2.

It is known that the ratio of the number of H and C atoms in their molecules is maximum when compared with other classes. Due to the fact that all valences are occupied by either C or H, the chemical properties of alkanes are not clearly expressed, so their second name is the phrase saturated or saturated hydrocarbons.

There is also an older name that best reflects their relative chemical inertness - paraffins, which means “devoid of affinity.”

So, the topic of our conversation today is: “Alkanes: homological series, nomenclature, structure, isomerism.” Data regarding their physical properties will also be presented.

Alkanes: structure, nomenclature

In them, the C atoms are in a state called sp3 hybridization. In this regard, the alkane molecule can be demonstrated as a set of tetrahedral C structures that are connected not only to each other, but also to H.

Between the C and H atoms there are strong, very low-polar s-bonds. Atoms always rotate around simple bonds, which is why alkane molecules take on various shapes, and the bond length and the angle between them are constant values. Shapes that transform into each other due to the rotation of the molecule around σ bonds are usually called conformations.

In the process of abstraction of an H atom from the molecule in question, 1-valent species called hydrocarbon radicals are formed. They appear as a result of not only but also inorganic compounds. If you subtract 2 hydrogen atoms from a saturated hydrocarbon molecule, you get 2-valent radicals.

Thus, the nomenclature of alkanes can be:

• radial (old version);
• substitution (international, systematic). It was proposed by IUPAC.

Features of radial nomenclature

In the first case, the nomenclature of alkanes is characterized as follows:

1. Consideration of hydrocarbons as derivatives of methane, in which 1 or several H atoms are replaced by radicals.
2. High degree of convenience in the case of not very complex connections.

Features of substitution nomenclature

The substitutive nomenclature of alkanes has the following features:

1. The basis for the name is 1 carbon chain, while the remaining molecular fragments are considered as substituents.
2. If there are several identical radicals, the number is indicated before their name (strictly in words), and the radical numbers are separated by commas.

Chemistry: nomenclature of alkanes

For convenience, the information is presented in table form.

The above nomenclature of alkanes includes names that have developed historically (the first 4 members of the series of saturated hydrocarbons).

The names of unexpanded alkanes with 5 or more C atoms are derived from Greek numerals that reflect the given number of C atoms. Thus, the suffix -an indicates that the substance is from a series of saturated compounds.

When composing the names of unfolded alkanes, the main chain is the one that contains the maximum number of C atoms. It is numbered so that the substituents have the lowest number. In the case of two or more chains of the same length, the main one becomes the one that contains the largest number of substituents.

Isomerism of alkanes

The parent hydrocarbon of their series is methane CH₄. With each subsequent representative of the methane series, a difference from the previous one is observed in the methylene group - CH₂. This pattern can be traced throughout the entire series of alkanes.

The German scientist Schiel put forward a proposal to call this series homological. Translated from Greek it means “similar, similar.”

Thus, a homologous series is a set of related organic compounds that have the same structure and similar chemical properties. Homologues are members of a given series. Homologous difference is a methylene group in which 2 neighboring homologues differ.

As mentioned earlier, the composition of any saturated hydrocarbon can be expressed using the general formula CnH₂n + 2. Thus, the next member of the homologous series after methane is ethane - C₂H₆. To convert its structure from methane, it is necessary to replace 1 H atom with CH₃ (figure below).

The structure of each subsequent homolog can be deduced from the previous one in the same way. As a result, propane is formed from ethane - C₃H₈.

What are isomers?

These are substances that have an identical qualitative and quantitative molecular composition (identical molecular formula), but a different chemical structure, and also have different chemical properties.

The hydrocarbons discussed above differ in such a parameter as boiling point: -0.5° - butane, -10° - isobutane. This type of isomerism is called carbon skeleton isomerism; it belongs to the structural type.

The number of structural isomers increases rapidly as the number of carbon atoms increases. Thus, C₁₀H₂₂ will correspond to 75 isomers (not including spatial ones), and for C₁₅H₃₂ 4347 isomers are already known, for C₂₀H₄₂ - 366,319.

So, it has already become clear what alkanes are, homologous series, isomerism, nomenclature. Now it’s worth moving on to the rules for compiling names according to IUPAC.

IUPAC nomenclature: rules for the formation of names

First, it is necessary to find in the hydrocarbon structure the carbon chain that is longest and contains the maximum number of substituents. Then you need to number the C atoms of the chain, starting from the end to which the substituent is closest.

Secondly, the base is the name of an unbranched saturated hydrocarbon, which, in terms of the number of C atoms, corresponds to the main chain.

Thirdly, before the base it is necessary to indicate the numbers of the locants near which the substituents are located. The names of the substituents are written after them with a hyphen.

Fourthly, in the case of the presence of identical substituents at different C atoms, the locants are combined, and a multiplying prefix appears before the name: di - for two identical substituents, three - for three, tetra - four, penta - for five, etc. Numbers must be separated from each other by a comma, and from words by a hyphen.

If the same C atom contains two substituents at once, the locant is also written twice.

According to these rules, the international nomenclature of alkanes is formed.

Newman projections

This American scientist proposed special projection formulas for graphical demonstration of conformations - Newman projections. They correspond to forms A and B and are presented in the figure below.

In the first case, this is an A-occluded conformation, and in the second, it is a B-inhibited conformation. In position A, the H atoms are located at a minimum distance from each other. This form corresponds to the highest energy value, due to the fact that the repulsion between them is greatest. This is an energetically unfavorable state, as a result of which the molecule tends to leave it and move to a more stable position B. Here the H atoms are as far apart as possible from each other. Thus, the energy difference between these positions is 12 kJ/mol, due to which the free rotation around the axis in the ethane molecule, which connects the methyl groups, is uneven. After entering an energetically favorable position, the molecule lingers there, in other words, “slows down.” That is why it is called inhibited. The result is that 10 thousand ethane molecules are in the inhibited form of conformation at room temperature. Only one has a different shape - obscured.

Obtaining saturated hydrocarbons

From the article it has already become known that these are alkanes (their structure and nomenclature were described in detail earlier). It would be useful to consider ways to obtain them. They are released from natural sources such as oil, natural, and coal. Synthetic methods are also used. For example, H₂ 2H₂:

1. Hydrogenation process CnH₂n (alkenes)→ CnH₂n+2 (alkanes)← CnH₂n-2 (alkynes).
2. From a mixture of C and H monoxide - synthesis gas: nCO+(2n+1)H₂→ CnH₂n+2+nH₂O.
3. From carboxylic acids (their salts): electrolysis at the anode, at the cathode:

• Kolbe electrolysis: 2RCOONa+2H₂O→R-R+2CO₂+H₂+2NaOH;
• Dumas reaction (alloy with alkali): CH₃COONa+NaOH (t)→CH₄+Na₂CO₃.

1. Oil cracking: CnH₂n+2 (450-700°)→ CmH₂m+2+ Cn-mH₂(n-m).
2. Gasification of fuel (solid): C+2H₂→CH₄.
3. Synthesis of complex alkanes (halogen derivatives) that have fewer C atoms: 2CH₃Cl (chloromethane) +2Na →CH₃- CH₃ (ethane) +2NaCl.
4. Decomposition of methanides (metal carbides) by water: Al₄C₃+12H₂O→4Al(OH₃)↓+3CH₄.

Physical properties of saturated hydrocarbons

For convenience, the data is grouped into a table.

Conclusion

The article examined such a concept as alkanes (structure, nomenclature, isomerism, homologous series, etc.). A little is said about the features of radial and substitutive nomenclatures. Methods for obtaining alkanes are described.

In addition, the article lists in detail the entire nomenclature of alkanes (the test can help you assimilate the information received).

Alkanes :

Alkanes are saturated hydrocarbons, in the molecules of which all atoms are connected by single bonds. Formula -

Physical properties :

• Melting and boiling points increase with molecular weight and length of the carbon backbone
• Under normal conditions, unbranched alkanes from CH 4 to C 4 H 10 are gases; from C 5 H 12 to C 13 H 28 - liquids; after C 14 H 30 - solids.
• Melting and boiling points decrease from less branched to more branched. So, for example, at 20 °C n-pentane is a liquid, and neopentane is a gas.

Chemical properties:

· Halogenation

this is one of the substitution reactions. The least hydrogenated carbon atom is halogenated first (tertiary atom, then secondary, primary atoms are halogenated last). The halogenation of alkanes occurs in stages - no more than one hydrogen atom is replaced in one stage:

1. CH 4 + Cl 2 → CH 3 Cl + HCl (chloromethane)
2. CH 3 Cl + Cl 2 → CH 2 Cl 2 + HCl (dichloromethane)
3. CH 2 Cl 2 + Cl 2 → CHCl 3 + HCl (trichloromethane)
4. CHCl 3 + Cl 2 → CCl 4 + HCl (carbon tetrachloride).

Under the influence of light, a chlorine molecule breaks down into radicals, then they attack alkane molecules, taking away a hydrogen atom from them, as a result of which methyl radicals CH 3 are formed, which collide with chlorine molecules, destroying them and forming new radicals.

· Combustion

The main chemical property of saturated hydrocarbons, which determines their use as fuel, is the combustion reaction. Example:

CH 4 + 2O 2 → CO 2 + 2H 2 O + Q

In case of lack of oxygen, carbon monoxide or coal is produced instead of carbon dioxide (depending on the oxygen concentration).

In general, the combustion reaction of alkanes can be written as follows:

WITH n H 2 n +2 +(1,5n+0.5)O 2 = n CO 2 + ( n+1)H 2 O

· Decomposition

Decomposition reactions occur only under the influence of high temperatures. An increase in temperature leads to the rupture of carbon bonds and the formation of free radicals.

Examples:

CH 4 → C + 2H 2 (t > 1000 °C)

C 2 H 6 → 2C + 3H 2

Alkenes :

Alkenes are unsaturated hydrocarbons containing in the molecule, in addition to single bonds, one carbon-carbon double bond. Formula - C n H 2n

The belonging of a hydrocarbon to the class of alkenes is reflected by the generic suffix –ene in its name.

Physical properties :

• The melting and boiling points of alkenes (simplified) increase with molecular weight and length of the carbon backbone.
• Under normal conditions, alkenes from C 2 H 4 to C 4 H 8 are gases; from C 5 H 10 to C 17 H 34 - liquids, after C 18 H 36 - solids. Alkenes are insoluble in water, but are highly soluble in organic solvents.

Chemical properties :

· Dehydration is the process of splitting off a water molecule from a molecule of an organic compound.

· Polymerization is a chemical process of combining many initial molecules of a low molecular weight substance into large polymer molecules.

Polymer is a high-molecular compound whose molecules consist of many identical structural units.

Alcadienes :

Alkadienes are unsaturated hydrocarbons containing in the molecule, in addition to single bonds, double carbon-carbon bonds. Formula -

Physical properties :

Butadiene is a gas (boiling point −4.5 °C), isoprene is a liquid boiling at 34 °C, dimethylbutadiene is a liquid boiling at 70 °C. Isoprene and other diene hydrocarbons are capable of polymerizing into rubber. Natural rubber in its purified state is a polymer with the general formula (C5H8)n and is obtained from the milky sap of some tropical plants.

Rubber is highly soluble in benzene, gasoline, and carbon disulfide. At low temperatures it becomes brittle and sticky when heated. To improve the mechanical and chemical properties of rubber, it is converted into rubber by vulcanization. To obtain rubber products, they are first molded from a mixture of rubber with sulfur, as well as fillers: soot, chalk, clay and some organic compounds that serve to accelerate vulcanization. Then the products are heated - hot vulcanization. During vulcanization, sulfur chemically bonds with the rubber. In addition, vulcanized rubber contains sulfur in a free state in the form of tiny particles.

Diene hydrocarbons polymerize easily. The polymerization reaction of diene hydrocarbons underlies the synthesis of rubber. They undergo addition reactions (hydrogenation, halogenation, hydrohalogenation):

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

Alkynes :

Alkynes are unsaturated hydrocarbons whose molecules contain, in addition to single bonds, one triple carbon-carbon bond. Formula-C n H 2n-2

Physical properties :

Alkynes resemble the corresponding alkenes in their physical properties. Lower (up to C 4) are colorless and odorless gases that have higher boiling points than their analogues in alkenes.

Alkynes are poorly soluble in water, but better in organic solvents.

Chemical properties :

Halogenation reactions

Alkynes are capable of adding one or two halogen molecules to form the corresponding halogen derivatives:

Hydration

In the presence of mercury salts, alkynes add water to form acetaldehyde (for acetylene) or ketone (for other alkynes)

I. ALKANES (saturated hydrocarbons, paraffins)

Alkanes are aliphatic (acyclic) saturated hydrocarbons in which the carbon atoms are linked together by simple (single) bonds in straight or branched chains.

DEFINITION

Alkanes are called saturated hydrocarbons, the molecules of which consist of carbon and hydrogen atoms connected to each other only by σ bonds.

Under normal conditions (at 25 o C and atmospheric pressure), the first four members of the homologous series of alkanes (C 1 - C 4) are gases. Normal alkanes from pentane to heptadecane (C 5 - C 17) are liquids, starting from C 18 and above are solids. As the relative molecular weight increases, the boiling and melting points of alkanes increase. With the same number of carbon atoms in the molecule, branched alkanes have lower boiling points than normal alkanes. The structure of the alkane molecule using methane as an example is shown in Fig. 1.

Rice. 1. The structure of the methane molecule.

Alkanes are practically insoluble in water, since their molecules are low-polar and do not interact with water molecules. Liquid alkanes mix easily with each other. They dissolve well in non-polar organic solvents such as benzene, carbon tetrachloride, diethyl ether, etc.

Preparation of alkanes

The main sources of various saturated hydrocarbons containing up to 40 carbon atoms are oil and natural gas. Alkanes with a small number of carbon atoms (1 - 10) can be isolated by fractional distillation of natural gas or the gasoline fraction of oil.

There are industrial (I) and laboratory (II) methods for producing alkanes.

C + H 2 → CH 4 (kat = Ni, t 0);

CO + 3H 2 → CH 4 + H 2 O (kat = Ni, t 0 = 200 - 300);

CO 2 + 4H 2 → CH 4 + 2H 2 O (kat, t 0).

— hydrogenation of unsaturated hydrocarbons

CH 3 -CH=CH 2 + H 2 →CH 3 -CH 2 -CH 3 (kat = Ni, t 0);

- reduction of haloalkanes

C 2 H 5 I + HI →C 2 H 6 + I 2 (t 0);

- alkaline melting reactions of salts of monobasic organic acids

C 2 H 5 -COONa + NaOH → C 2 H 6 + Na 2 CO 3 (t 0);

— interaction of haloalkanes with sodium metal (Wurtz reaction)

2C 2 H 5 Br + 2Na → CH 3 -CH 2 -CH 2 -CH 3 + 2NaBr;

— electrolysis of salts of monobasic organic acids

2C 2 H 5 COONa + 2H 2 O → H 2 + 2NaOH + C 4 H 10 + 2CO 2 ;

K(-): 2H 2 O + 2e → H 2 + 2OH - ;

A(+):2C 2 H 5 COO — -2e → 2C 2 H 5 COO + → 2C 2 H 5 + + 2CO 2 .

Chemical properties of alkanes

Alkanes are among the least reactive organic compounds, which is explained by their structure.

Alkanes under normal conditions do not react with concentrated acids, molten and concentrated alkalis, alkali metals, halogens (except fluorine), potassium permanganate and potassium dichromate in an acidic environment.

For alkanes, the most typical reactions are those that proceed by a radical mechanism. Homolytic cleavage of C-H and C-C bonds is energetically more favorable than their heterolytic cleavage.

Radical substitution reactions most easily occur at the tertiary carbon atom, then at the secondary carbon atom, and lastly at the primary carbon atom.

All chemical transformations of alkanes proceed with splitting:

1) C-H bonds

— halogenation (S R)

CH 4 + Cl 2 → CH 3 Cl + HCl ( hv);

CH 3 -CH 2 -CH 3 + Br 2 → CH 3 -CHBr-CH 3 + HBr ( hv).

- nitration (S R)

CH 3 -C(CH 3)H-CH 3 + HONO 2 (dilute) → CH 3 -C(NO 2)H-CH 3 + H 2 O (t 0).

— sulfochlorination (S R)

R-H + SO 2 + Cl 2 → RSO 2 Cl + HCl ( hv).

- dehydrogenation

CH 3 -CH 3 → CH 2 =CH 2 + H 2 (kat = Ni, t 0).

- dehydrocyclization

CH 3 (CH 2) 4 CH 3 → C 6 H 6 + 4H 2 (kat = Cr 2 O 3, t 0).

2) C-H and C-C bonds

- isomerization (intramolecular rearrangement)

CH 3 -CH 2 -CH 2 -CH 3 →CH 3 -C(CH 3)H-CH 3 (kat=AlCl 3, t 0).

- oxidation

2CH 3 -CH 2 -CH 2 -CH 3 + 5O 2 → 4CH 3 COOH + 2H 2 O (t 0 , p);

C n H 2n+2 + (1.5n + 0.5) O 2 → nCO 2 + (n+1) H 2 O (t 0).

Applications of alkanes

Alkanes have found application in various industries. Let us consider in more detail, using the example of some representatives of the homologous series, as well as mixtures of alkanes.

Methane forms the raw material basis for the most important chemical industrial processes for the production of carbon and hydrogen, acetylene, oxygen-containing organic compounds - alcohols, aldehydes, acids. Propane is used as automobile fuel. Butane is used to produce butadiene, which is a raw material for the production of synthetic rubber.

A mixture of liquid and solid alkanes up to C 25, called Vaseline, is used in medicine as the basis of ointments. A mixture of solid alkanes C 18 - C 25 (paraffin) is used to impregnate various materials (paper, fabrics, wood) to give them hydrophobic properties, i.e. non-wetting with water. In medicine it is used for physiotherapeutic procedures (paraffin treatment).

Examples of problem solving

EXAMPLE 1

EXAMPLE 2

Exercise

Determine the molecular formula of trichloroalkane, the mass fraction of chlorine in which is 72.20%. Draw up the structural formulas of all possible isomers and give the names of the substances according to the IUPAC substitutive nomenclature.

Answer

Let's write down the general formula of trichloroalkean: C n H 2 n -1 Cl 3 . According to the formula ω(Cl) = 3×Ar(Cl) / Mr(C n H 2 n -1 Cl 3) × 100% Let's calculate the molecular weight of trichloroalkane: Mr(C n H 2 n -1 Cl 3) = 3 × 35.5 / 72.20 × 100% = 147.5. Let's find the value of n: 12n + 2n - 1 + 35.5×3 = 147.5; Therefore, the formula of trichloroalkane is C 3 H 5 Cl 3. Let's compose the structural formulas of the isomers: 1,2,3-trichloropropane (1), 1,1,2-trichloropropane (2), 1,1,3-trichloropropane (3), 1,1,1-trichloropropane (4) and 1 ,2,2-trichloropropane (5). CH 2 Cl-CHCl-CH 2 Cl (1); CHCl 2 -CHCl-CH 3 (2); CHCl 2 -CH 2 -CH 2 Cl (3); CCl 3 -CH 2 -CH 3 (4); Physical properties. Under normal conditions, the first four members of the homologous series of alkanes (C 1 - C 4) are gases. Normal alkanes from pentane to heptadecane ( C 5 - C 17 ) - liquids, starting from C 18 and above - solids. As the number of carbon atoms in the chain increases, i.e. As the relative molecular weight increases, the boiling and melting points of alkanes increase. With the same number of carbon atoms in the molecule, branched alkanes have lower boiling points than normal alkanes. Alkanespractically insoluble in water, since their molecules are slightly polar and do not interact with water molecules, they dissolve well in non-polar organic solvents such as benzene, carbon tetrachloride, etc. Liquid alkanes are easily mixed with each other. The main natural sources of alkanes are oil and natural gas. Various petroleum fractions contain alkanes from C5H12 to C 30 H 62. Natural gas consists of methane (95%) with an admixture of ethane and propane. From synthetic methods for obtaining alkanes The following can be distinguished:/> 1 . Obtained from unsaturated hydrocarbons. The interaction of alkenes or alkynes with hydrogen (“hydrogenation”) occurs in the presence of metal catalysts (/>Ni, Pd ) at heating: CH z - C ≡CH+ 2H 2 → CH 3 -CH 2 -CH 3. 2. Receiving from halogen-conducted. When monohalogenated alkanes are heated with sodium metal, alkanes with double the number of carbon atoms are obtained (Wurtz reaction): C 2 H 5 Br + 2 Na + Br - C 2 H 5 → C 2 H 5 - C 2 H 5 + 2 NaBr. A similar reaction is not carried out with two different halogenated alkanes, since this produces a mixture of three different alkanes 3. Preparation from salts of carboxylic acids. When anhydrous salts of carboxylic acids are fused with alkalis, alkanes are obtained containing one less carbon atom compared to the carbon chain of the original carboxylic acids: 4.Methane production. An electric arc burning in a hydrogen atmosphere produces a significant amount of methane: C + 2H 2 → CH 4 . The same reaction occurs when carbon is heated in a hydrogen atmosphere to 400-500 °C at elevated pressure in the presence of a catalyst. In laboratory conditions, methane is often obtained from aluminum carbide: A l 4 C 3 + 12H 2 O = ZSN 4 + 4A l (OH) 3 . Chemical properties. Under normal conditions, alkanes are chemically inert. They are resistant to the action of many reagents: they do not interact with concentrated sulfuric and nitric acids, with concentrated and molten alkalis, and are not oxidized by strong oxidizing agents - potassium permanganateKMn O 4, etc. The chemical stability of alkanes is explained by their high strengths—C-C and C-H bonds, as well as their non-polarity. Non-polar C-C and C-H bonds in alkanes are not prone to ionic cleavage, but are capable of homolytic cleavage under the influence of active free radicals. Therefore, alkanes are characterized by radical reactions, which result in compounds where hydrogen atoms are replaced by other atoms or groups of atoms. Consequently, alkanes enter into reactions that proceed through the mechanism of radical substitution, denoted by the symbol S R ( from English, substitution radicalic). According to this mechanism, hydrogen atoms are most easily replaced at tertiary, then at secondary and primary carbon atoms. 1. Halogenation. When alkanes interact with halogens (chlorine and bromine) under the influence of UV radiation or high temperature, a mixture of products from mono- to polyhalogen-substituted alkanes The general scheme of this reaction is shown using methane as an example: b) Growth of the chain. The chlorine radical removes a hydrogen atom from the alkane molecule: Cl· + CH 4 →HC/>l + CH 3 · In this case, an alkyl radical is formed, which removes a chlorine atom from the chlorine molecule: CH 3 + C l 2 →CH 3 C l + C l· These reactions are repeated until the chain breaks in one of the reactions: Cl· + Cl· → С l/> 2, СН 3 · + СН 3 · → С 2 Н 6, СН 3 · + Cl· → CH 3 С l · Overall reaction equation: hv CH 4 + Cl 2 → CH 3 Cl + HCl. The resulting chloromethane can be further chlorinated, giving a mixture of products CH 2 Cl 2, CHCl 3, CC l 4 according to the scheme (*). Development of chain theory free radical reactions is closely connected with the name of the outstanding Russian scientist, Nobel Prize laureate N.I. Semenov (1896-1986). 2. Nitration (Konovalov reaction). When dilute nitric acid acts on alkanes at 140°C and low pressure, a radical reaction occurs: In radical reactions (halogenation, nitration), hydrogen atoms at tertiary carbon atoms are mixed first, then at secondary and primary carbon atoms.This is explained by the fact that the bond between the tertiary carbon atom and hydrogen is most easily broken homolytically (bond energy 376 kJ/mol), then the secondary one (390 kJ/mol), and only then the primary one (415 kJ/mol). 3. Isomerization. Normal alkanes can, under certain conditions, transform into branched-chain alkanes: 4. Cracking is a hemolytic cleavage of C-C bonds, which occurs when heated and under the influence of catalysts. When higher alkanes are cracked, alkenes and lower alkanes are formed; when methane and ethane are cracked, acetylene is formed: C/> 8 H 18 → C 4 H 10 + C 4 H 8 ,/> 2CH 4 → C 2 H 2 + ZN 2, C 2 H 6 → C 2 H 2 + 2H 2. These reactions are of great industrial importance. In this way, high-boiling oil fractions (fuel oil) are converted into gasoline, kerosene and other valuable products. 5. Oxidation. By mild oxidation of methane with atmospheric oxygen in the presence of various catalysts, methyl alcohol, formaldehyde, and formic acid can be obtained: Mild catalytic oxidation of butane with atmospheric oxygen is one of the industrial methods for producing acetic acid: t° 2 C 4/>H/>10 + 5 O/>2 → 4 CH/>3 COOH/>+ 2H 2 O . cat Alkanes in air burn to CO 2 and H 2 O:/> С n Н 2 n +2 + (З n+1)/2O 2 = n CO 2 + (n +1) H 2 O. 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