Organic chemistry - branch of chemistry that studies carbon compounds, their structure, properties , methods of synthesis, as well as the laws of their transformations. Organic compounds are called carbon compounds with other elements (mainly with H, N, O, S, P, Si, Ge, etc.).

The unique ability of carbon atoms to bind to each other, forming chains of various lengths, cyclic structures of various sizes, framework compounds, compounds with many elements, different in composition and structure, determines the diversity of organic compounds. To date, the number of known organic compounds is much more than 10 million and increases every year by 250-300 thousand. The world around us is built mainly from organic compounds, these include: food, clothing, fuel, dyes, medicines, detergents, materials for various branches of technology and the national economy. Organic compounds play a key role in the existence of living organisms.

At the junction of organic chemistry with inorganic chemistry, biochemistry and medicine, the chemistry of organometallic and elemental compounds, bioorganic and medical chemistry, and the chemistry of macromolecular compounds arose.

The main method of organic chemistry is synthesis. Organic chemistry studies not only compounds derived from plant and animal sources (natural substances), but mainly compounds created artificially through laboratory and industrial synthesis.

History of the development of organic chemistry

Methods for obtaining various organic substances have been known since antiquity. So, the Egyptians and Romans used dyes of plant origin - indigo and alizarin. Many nations owned the secrets of the production of alcoholic beverages and vinegar from sugar and starch-containing raw materials.

During the Middle Ages, practically nothing was added to this knowledge, some progress began only in the 16-17 centuries (the period of iatrochemistry), when new organic compounds were isolated by distillation of plant products. In 1769-1785 K.V. Scheele isolated several organic acids: malic, tartaric, citric, gallic, lactic and oxalic. In 1773 G.F. Ruel isolated urea from human urine. Substances isolated from animal and vegetable raw materials had much in common, but differed from inorganic compounds. This is how the term "Organic Chemistry" arose - a branch of chemistry that studies substances isolated from organisms (definition Y.Ya. Berzelius, 1807). At the same time, it was believed that these substances can only be obtained in living organisms due to the "life force".

It is generally accepted that organic chemistry as a science appeared in 1828, when F. Wöhler first received an organic substance - urea - as a result of evaporation of an aqueous solution of an inorganic substance - ammonium cyanate (NH 4 OCN). Further experimental work demonstrated indisputable arguments of the inconsistency of the "life force" theory. For example, A. Kolbe synthesized acetic acid, M. Berthelot received methane from H 2 S and CS 2, and A.M. Butlerov synthesized saccharides from formalin.

In the middle of the 19th century the rapid development of synthetic organic chemistry continues, the first industrial production of organic substances is created ( A. Hoffman, W. Perkin Sr.- synthetic dyes, fuchsin, cyanine and aza dyes). Open N.N. Zinin(1842) of the method for the synthesis of aniline served as the basis for the creation of the aniline-dye industry. In the laboratory A. Bayer natural dyes were synthesized - indigo, alizarin, indigo, xanthene and anthraquinone.

An important stage in the development of theoretical organic chemistry was the development F. Kekule theory of valency in 1857, as well as the classical theory of chemical structure A.M. Butlerov in 1861, according to which atoms in molecules are combined in accordance with their valence, the chemical and physical properties of compounds are determined by the nature and number of atoms in them, as well as the type of bonds and the mutual influence of directly unbound atoms. In 1865 F. Kekule proposed the structural formula of benzene, which became one of the most important discoveries in organic chemistry. V.V. Markovnikov And A.M. Zaitsev formulated a number of rules that for the first time connected the direction of organic reactions with the structure of the substances entering into them. In 1875 Van't Hoff And Le Bel proposed a tetrahedral model of the carbon atom, according to which the valences of carbon are directed to the vertices of the tetrahedron, in the center of which the carbon atom is located. Based on this model, combined with experimental studies I. Wislicenus(! 873), which showed the identity of the structural formulas of (+)-lactic acid (from sour milk) and (±)-lactic acid, stereochemistry arose - the science of the three-dimensional orientation of atoms in molecules, which predicted in the case of the presence of 4 different substituents at carbon atom (chiral structures) the possibility of the existence of space-mirror isomers (antipodes or enantiomers).

In 1917 Lewis proposed to consider the chemical bond using electron pairs.

In 1931 Hückel applied quantum theory to explain the properties of non-benzenoid aromatic systems, which founded a new direction in organic chemistry - quantum chemistry. This served as an impetus for the further intensive development of quantum chemical methods, in particular the method of molecular orbitals. The stage of penetration of orbital representations into organic chemistry was opened by the theory of resonance L. Pauling(1931-1933) and further work K. Fukui, R. Woodward And R. Hoffmann on the role of frontier orbitals in determining the direction of chemical reactions.

Mid 20th century characterized by a particularly rapid development of organic synthesis. This was determined by the discovery of fundamental processes, such as the production of olefins using ylides ( G. Wittig, 1954), diene synthesis ( O. Diels And C. Alder, 1928), hydroboration of unsaturated compounds ( G. Brown, 1959), nucleotide synthesis and gene synthesis ( A. Todd, H. Qur'an). Advances in the chemistry of organometallic compounds are largely due to the work A.N. Nesmeyanov And G.A. Razuvaeva. In 1951, the synthesis of ferrocene was carried out, the establishment of the "sandwich" structure of which R. Woodward And J. Wilkinson marked the beginning of the chemistry of metallocene compounds and, in general, the organic chemistry of transition metals.

In 20-30 years. A.E. Arbuzov creates the foundations of the chemistry of organophosphorus compounds, which subsequently led to the discovery of new types of physiologically active compounds, complexons, etc.

In the 60-80s. Ch. Pedersen, D. Cram And J.M. Linen develop the chemistry of crown ethers, cryptands and other related structures capable of forming strong molecular complexes, and thus approach the most important problem of "molecular recognition".

Modern organic chemistry continues its rapid development. New reagents, fundamentally new synthetic methods and techniques, new catalysts are introduced into the practice of organic synthesis, previously unknown organic structures are synthesized. The search for organic new biologically active compounds is constantly being conducted. Many more problems of organic chemistry are waiting to be solved, for example, a detailed establishment of the structure-property relationship (including biological activity), the establishment of the structure and stereodirected synthesis of complex natural compounds, the development of new regio- and stereoselective synthetic methods, the search for new universal reagents and catalysts .

The interest of the world community in the development of organic chemistry was vividly demonstrated by the awarding of the Nobel Prize in Chemistry in 2010. R. Heku, A. Suzuki and E. Negishi for his work on the use of palladium catalysts in organic synthesis for the formation of carbon-carbon bonds.

Classification of organic compounds

The classification is based on the structure of organic compounds. The basis of the description of the structure is the structural formula.

Main classes of organic compounds

Hydrocarbons - compounds consisting only of carbon and hydrogen. They, in turn, are divided into:

Saturated- contain only single (σ-bonds) and do not contain multiple bonds;

Unsaturated- contain at least one double (π-bond) and/or triple bond;

open chain(alicyclic);

closed circuit(cyclic) - contain a cycle

These include alkanes, alkenes, alkynes, dienes, cycloalkanes, arenes

Compounds with heteroatoms in functional groups- compounds in which the carbon radical R is associated with a functional group. Such compounds are classified according to the nature of the functional group:

Alcohol, phenols(contain hydroxyl group OH)

Ethers(contain the grouping R-O-R or R-O-R

Carbonyl compounds(contain the group RR "C = O), these include aldehydes, ketones, quinones.

Compounds containing a carboxyl group(COOH or COOR), these include carboxylic acids, esters

Element- and organometallic compounds

Heterocyclic compounds - contain heteroatoms in the ring. They differ in the nature of the cycle (saturated, aromatic), in the number of atoms in the cycle (three-, four-, five-, six-membered cycles, etc.), in the nature of the heteroatom, in the number of heteroatoms in the cycle. This determines the huge variety of known and annually synthesized compounds of this class. The chemistry of heterocycles is one of the most exciting and important areas of organic chemistry. Suffice it to say that more than 60% of drugs of synthetic and natural origin belong to various classes of heterocyclic compounds.

Natural compounds - compounds, as a rule, of a rather complex structure, often belonging to several classes of organic compounds at once. Among them are: amino acids, proteins, carbohydrates, alkaloids, terpenes, etc.

Polymers- substances with a very large molecular weight, consisting of periodically repeating fragments - monomers.

The structure of organic compounds

Organic molecules are mainly formed by covalent non-polar C-C bonds, or covalent polar bonds of the C-O, C-N, C-Hal type. Polarity is explained by the shift of the electron density towards the more electronegative atom. To describe the structure of organic compounds, chemists use the language of structural formulas of molecules, in which bonds between individual atoms are denoted by one (simple, or single bond), two (double), or three (triple) valence strokes. The concept of a valency stroke, which has not lost its meaning to this day, was introduced into organic chemistry A. Cooper in 1858

Very important for understanding the structure of organic compounds is the concept of hybridization of carbon atoms. The carbon atom in the ground state has an electronic configuration 1s 2 2s 2 2p 2, on the basis of which it is impossible to explain the valency 4 inherent in carbon in its compounds and the existence of 4 identical bonds in alkanes directed to the vertices of the tetrahedron. In the framework of the method of valence bonds, this contradiction is resolved by introducing the concept of hybridization. When excited, s→p electron transition and the subsequent, so-called, sp- hybridization, with the energy of the hybridized orbitals being intermediate between the energies s- And p-orbitals. When bonds are formed in alkanes, three R-electron interact with one s-electron ( sp 3 hybridization) and 4 identical orbitals arise, located at tetrahedral angles (109 about 28 ") to each other. Carbon atoms in alkenes are in sp 2-hybrid state: each carbon atom has three identical orbitals lying in the same plane at an angle of 120 about to each other ( sp 2 orbitals), and the fourth ( R-orbital) is perpendicular to this plane. Overlapping R-orbitals of two carbon atoms forms a double (π) bond. The carbon atoms that carry the triple bond are in sp- hybrid state.

Features of organic reactions

Ions are usually involved in inorganic reactions, such reactions proceed quickly and are completed at room temperature. In organic reactions, covalent bonds are often broken with the formation of new ones. As a rule, these processes require special conditions: a certain temperature, reaction time, certain solvents, and often the presence of a catalyst. Usually, not one, but several reactions take place at once. Therefore, when depicting organic reactions, not equations are used, but schemes without calculating stoichiometry. The yields of target substances in organic reactions often do not exceed 50%, and their isolation from the reaction mixture and purification require specific methods and techniques. To purify solids, as a rule, recrystallization from specially selected solvents is used. Liquid substances are purified by distillation at atmospheric pressure or under vacuum (depending on the boiling point). To control the progress of reactions, separate complex reaction mixtures, various types of chromatography are used [thin-layer chromatography (TLC), preparative high-performance liquid chromatography (HPLC), etc.].

Reactions can proceed very complicatedly and in several stages. Radicals R·, carbocations R + , carbanions R - , carbenes:CX 2 , radical cations, radical anions and other active and unstable particles, usually living for a fraction of a second, can appear as intermediate compounds. A detailed description of all the transformations that occur at the molecular level during a reaction is called reaction mechanism. According to the nature of the gap and the formation of bonds, radical (homolytic) and ionic (heterolytic) processes are distinguished. According to the types of transformations, chain radical reactions, nucleophilic (aliphatic and aromatic) substitution reactions, elimination reactions, electrophilic addition, electrophilic substitution, condensation, cyclization, rearrangement processes, etc. are distinguished. Reactions are also classified according to the methods of their initiation (excitation ), their kinetic order (monomolecular, bimolecular, etc.).

Determination of the structure of organic compounds

Throughout the existence of organic chemistry as a science, the most important task has been to determine the structure of organic compounds. This means to find out which atoms are part of the structure, in what order and how these atoms are interconnected and how they are located in space.

There are several methods for solving these problems.

• elemental analysis consists in the fact that the substance is decomposed into simpler molecules, by the number of which it is possible to determine the number of atoms that make up the compound. This method does not make it possible to establish the order of bonds between atoms. Often used only to confirm the proposed structure.
• Infrared spectroscopy (IR spectroscopy) and Raman spectroscopy (Raman spectroscopy). The method is based on the fact that the substance interacts with electromagnetic radiation (light) of the infrared range (absorption is observed in IR spectroscopy, and radiation scattering is observed in Raman spectroscopy). This light, when absorbed, excites the vibrational and rotational levels of the molecules. The reference data are the number, frequency and intensity of vibrations of the molecule associated with a change in the dipole moment (IC) or polarizability (CR). The method allows you to establish the presence of functional groups, and is also often used to confirm the identity of a substance with some already known substance by comparing their spectra.
• Mass spectrometry. A substance under certain conditions (electron impact, chemical ionization, etc.) turns into ions without loss of atoms (molecular ions) and with loss (fragmentation, fragmentary ions). The method allows you to determine the molecular weight of a substance, its isotopic composition, and sometimes the presence of functional groups. The nature of the fragmentation allows us to draw some conclusions about the structural features and recreate the structure of the compound under study.
• Nuclear magnetic resonance (NMR) method is based on the interaction of nuclei with their own magnetic moment (spin) and placed in an external constant magnetic field (spin reorientation), with variable electromagnetic radiation in the radio frequency range. NMR is one of the most important and informative methods for determining the chemical structure. The method is also used to study the spatial structure and dynamics of molecules. Depending on the nuclei interacting with radiation, there are, for example, the method of proton resonance PMR, NMR 1 H), which allows you to determine the position of hydrogen atoms in a molecule. The 19 F NMR method makes it possible to determine the presence and position of fluorine atoms. The 31 P NMR method provides information on the presence, valence state, and position of phosphorus atoms in a molecule. The 13 C NMR method makes it possible to determine the number and types of carbon atoms; it is used to study the carbon skeleton of a molecule. Unlike the first three, the last method uses a minor isotope of the element, since the nucleus of the main 12 C isotope has zero spin and cannot be observed by NMR.
• Method of ultraviolet spectroscopy (UV spectroscopy) or electronic transition spectroscopy. The method is based on the absorption of electromagnetic radiation in the ultraviolet and visible regions of the spectrum during the transition of electrons in a molecule from the upper filled energy levels to vacant ones (excitation of the molecule). Most often used to determine the presence and characteristics of conjugate π-systems.
• Methods of analytical chemistry make it possible to determine the presence of certain functional groups by specific chemical (qualitative) reactions, the fact of which can be fixed visually (for example, the appearance or change in color) or using other methods. In addition to chemical methods of analysis in organic chemistry, instrumental analytical methods such as chromatography (thin-layer, gas, liquid) are increasingly used. A place of honor among them is occupied by chromatography-mass spectrometry, which makes it possible not only to assess the degree of purity of the obtained compounds, but also to obtain mass-spectral information about the components of complex mixtures.
• Methods for studying the stereochemistry of organic compounds. From the beginning of the 80s. the expediency of developing a new direction in pharmacology and pharmacy associated with the creation of enantiomerically pure drugs with an optimal ratio of therapeutic efficacy and safety has become obvious. Currently, approximately 15% of all synthesized pharmaceuticals are represented by pure enantiomers. This trend was reflected in the appearance in the scientific literature of recent years of the term chiral switch, which in Russian translation means “switching to chiral molecules”. In this regard, methods for establishing the absolute configuration of chiral organic molecules and determining their optical purity are of particular importance in organic chemistry. The main method for determining the absolute configuration should be considered X-ray diffraction analysis (XRD), and optical purity - chromatography on columns with a stationary chiral phase and NMR using special additional chiral reagents.

The connection of organic chemistry with the chemical industry

The main method of organic chemistry - synthesis - closely links organic chemistry with the chemical industry. Based on the methods and developments of synthetic organic chemistry, small-tonnage (fine) organic synthesis arose, including the production of drugs, vitamins, enzymes, pheromones, liquid crystals, organic semiconductors, solar cells, etc. The development of large-tonnage (basic) organic synthesis is also based on the achievements of organic chemistry. The main organic synthesis includes the production of artificial fibers, plastics, processing of oil, gas and coal raw materials.

Recommended reading

• G.V. Bykov, History of organic chemistry, M.: Mir, 1976 (http://gen.lib/rus.ec/get?md5=29a9a3f2bdc78b44ad0bad2d9ab87b87)
• J. March, Organic chemistry: reactions, mechanisms and structure, in 4 volumes, M.: Mir, 1987
• F. Carey, R. Sandberg, Advanced Course in Organic Chemistry, in 2 volumes, M.: Chemistry, 1981
• O.A. Reutov, A.L. Kurtz, K.P. Butin, Organic chemistry, in 4 parts, M .: "Binom, Knowledge Laboratory", 1999-2004. (http://edu.prometey.org./library/author/7883.html)
• Chemical Encyclopedia, ed. Knunyants, M.: "Great Russian Encyclopedia", 1992.

section of chemical science that studies hydrocarbons substances containing carbon and hydrogen, as well as various derivatives of these compounds, including oxygen, nitrogen and halogen atoms. All such compounds are called organic.

Organic chemistry arose in the process of studying those substances that were extracted from plant and animal organisms, consisting mostly of organic compounds. This is what determined the purely historical name of such compounds (organism organic). Some technologies of organic chemistry arose in ancient times, for example, alcoholic and acetic fermentation, the use of organic indigo and alizarin dyes, leather tanning processes, etc. For a long time, chemists could only isolate and analyze organic compounds, but could not obtain them artificially, as a result, the belief arose that organic compounds can only be obtained with the help of living organisms. Starting from the second half of the 19th century. methods of organic synthesis began to develop intensively, which made it possible to gradually overcome the established delusion. For the first time, the synthesis of organic compounds in the laboratory was carried out by F. Wöhler ne (in the period 18241828), during the hydrolysis of cyanogen, he obtained oxalic acid, which had previously been isolated from plants, and by heating ammonium cyanate due to the rearrangement of the molecule ( cm. ISOMERIA) received urea, a waste product of living organisms (Fig. 1).

Rice. 1. THE FIRST SYNTHESES OF ORGANIC COMPOUNDS

Now many of the compounds present in living organisms can be obtained in the laboratory, in addition, chemists are constantly obtaining organic compounds that are not found in living nature.

The formation of organic chemistry as an independent science took place in the middle of the 19th century, when, thanks to the efforts of chemical scientists, ideas about the structure of organic compounds began to form. The most prominent role was played by the works of E. Frankland (he defined the concept of valency), F. Kekule (established the tetravalence of carbon and the structure of benzene), A. Cooper (proposed the symbol of the valence line that is still used today, connecting atoms when depicting structural formulas), A.M. Butlerov (created the theory of chemical structure, which is based on the position according to which the properties of a compound are determined not only by its composition, but also by the order in which the atoms are connected).

The next important stage in the development of organic chemistry is associated with the work of J. van't Hoff, who changed the very way of thinking of chemists, proposing to move from a flat image of structural formulas to the spatial arrangement of atoms in a molecule, as a result, chemists began to consider molecules as volumetric bodies.

Ideas about the nature of chemical bonds in organic compounds were first formulated by G. Lewis, who suggested that atoms in a molecule are connected by electrons: a pair of generalized electrons creates a simple bond, and two or three pairs form, respectively, a double and triple bond. Considering the distribution of electron density in molecules (for example, its displacement under the influence of electronegative atoms O, Cl, etc.), chemists were able to explain the reactivity of many compounds, i.e. the possibility of their participation in certain reactions.

Accounting for the properties of the electron, determined by quantum mechanics, led to the development of quantum chemistry, using the concept of molecular orbitals. Now quantum chemistry, which has shown its predictive power in many examples, is successfully collaborating with experimental organic chemistry.

A small group of carbon compounds are not classified as organic: carbonic acid and its salts (carbonates), hydrocyanic acid HCN and its salts (cyanides), metal carbides and some other carbon compounds that are studied by inorganic chemistry.

The main feature of organic chemistry is the exceptional variety of compounds that arose due to the ability of carbon atoms to combine with each other in an almost unlimited number, forming molecules in the form of chains and cycles. Even greater diversity is achieved by including oxygen, nitrogen, etc. atoms between carbon atoms. The phenomenon of isomerism, due to which molecules with the same composition can have a different structure, further increases the variety of organic compounds. More than 10 million organic compounds are now known, and their number is increasing by 200-300 thousand annually.

Classification of organic compounds. Hydrocarbons are taken as the basis for the classification, they are considered basic compounds in organic chemistry. All other organic compounds are considered as their derivatives.

When systematizing hydrocarbons, the structure of the carbon skeleton and the type of bonds connecting carbon atoms are taken into account.

I. ALIPHATIC (aleiphatos. Greek oil) hydrocarbons are linear or branched chains and do not contain cyclic fragments, they form two large groups.

1. Saturated or saturated hydrocarbons (so named because they are not capable of attaching anything) are chains of carbon atoms connected by simple bonds and surrounded by hydrogen atoms (Fig. 1). In the case when the chain has branches, a prefix is ​​added to the name iso. The simplest saturated hydrocarbon is methane; a series of these compounds begins with it.

Rice. 2. SATURATED HYDROCARBONS

The main sources of saturated hydrocarbons are oil and natural gas. The reactivity of saturated hydrocarbons is very low, they can only react with the most aggressive substances, such as halogens or nitric acid. When saturated hydrocarbons are heated above 450 ° C without air access, C-C bonds are broken and compounds with a shortened carbon chain are formed. High-temperature exposure in the presence of oxygen leads to their complete combustion to CO 2 and water, which allows them to be effectively used as a gaseous (methane propane) or liquid motor fuel (octane).

When one or more hydrogen atoms are replaced by some functional (i.e., capable of subsequent transformations) group, the corresponding hydrocarbon derivatives are formed. Compounds containing the C-OH group are called alcohols, HC \u003d O aldehydes, COOH carboxylic acids (the word "carboxylic" is added to distinguish them from ordinary mineral acids, for example, hydrochloric or sulfuric). A compound can simultaneously contain various functional groups, for example, COOH and NH 2, such compounds are called amino acids. The introduction of halogens or nitro groups into the hydrocarbon composition leads, respectively, to halogen or nitro derivatives (Fig. 3).

Rice. 4. EXAMPLES OF SATURATED HYDROCARBONS with functional groups

All hydrocarbon derivatives shown form large groups of organic compounds: alcohols, aldehydes, acids, halogen derivatives, etc. Since the hydrocarbon part of the molecule has a very low reactivity, the chemical behavior of such compounds is determined by the chemical properties of the functional groups OH, -COOH, -Cl, -NO 2, etc.

2. Unsaturated hydrocarbons have the same variants of the main chain structure as saturated hydrocarbons, but contain double or triple bonds between carbon atoms (Fig. 6). The simplest unsaturated hydrocarbon is ethylene.

Rice. 6. UNSATURATED HYDROCARBONS

The most typical for unsaturated hydrocarbons is the addition by a multiple bond (Fig. 8), which makes it possible to synthesize various organic compounds on their basis.

Rice. 8. ADDING REAGENTS to unsaturated compounds by multiple bond

Another important property of compounds with double bonds is their ability to polymerize (Fig. 9.), Double bonds are opened in this case, resulting in the formation of long hydrocarbon chains.

Rice. 9. POLYMERIZATION OF ETHYLENE

The introduction of the previously mentioned functional groups into the composition of unsaturated hydrocarbons, just as in the case of saturated hydrocarbons, leads to the corresponding derivatives, which also form large groups of the corresponding organic compounds - unsaturated alcohols, aldehydes, etc. (Fig. 10).

Rice. 10. UNSATURATED HYDROCARBONS with functional groups

For the compounds shown, simplified names are given, the exact position in the molecule of multiple bonds and functional groups is indicated in the name of the compound, which is compiled according to specially developed rules.

The chemical behavior of such compounds is determined both by the properties of multiple bonds and by the properties of functional groups.

II. CARBOCYCLIC HYDROCARBONS contain cyclic fragments formed only by carbon atoms. They form two large groups.

1. Alicyclic (i.e. both aliphatic and cyclic at the same time) hydrocarbons. In these compounds, cyclic fragments can contain both single and multiple bonds, in addition, compounds can contain several cyclic fragments, the prefix “cyclo” is added to the name of these compounds, the simplest alicyclic compound is cyclopropane (Fig. 12).

Rice. 12. ALICYCLIC HYDROCARBONS

In addition to those shown above, there are other options for connecting cyclic fragments, for example, they can have one common atom (the so-called spirocyclic compounds), or they can be connected in such a way that two or more atoms are common to both cycles (bicyclic compounds), by combining three and more cycles, the formation of hydrocarbon frameworks is also possible (Fig. 14).

Rice. 14. OPTIONS FOR CONNECTING CYCLES in alicyclic compounds: spirocycles, bicycles and frameworks. The name of spiro- and bicyclic compounds indicate that aliphatic hydrocarbon that contains the same total number of carbon atoms, for example, the spirocycle shown in the figure contains eight carbon atoms, so its name is built on the basis of the word "octane". In adamantane, the atoms are arranged in the same way as in the crystal lattice of diamond, which determined its name ( Greek adamantos diamond)

Many mono- and bicyclic alicyclic hydrocarbons, as well as adamantane derivatives, are part of oil, their general name is naphthenes.

In terms of chemical properties, alicyclic hydrocarbons are close to the corresponding aliphatic compounds, however, they have an additional property associated with their cyclic structure: small cycles (36-membered) are able to open by adding some reagents (Fig. 15).

Rice. 15. REACTIONS OF ALICYCLIC HYDROCARBONS, proceeding with the opening of the cycle

The introduction of various functional groups into the composition of alicyclic hydrocarbons leads to the corresponding derivatives alcohols, ketones, etc. (Fig. 16).

Rice. 16. ALICYCLIC HYDROCARBONS with functional groups

2. The second large group of carbocyclic compounds is formed by aromatic hydrocarbons of the benzene type, i.e. containing one or more benzene rings in their composition (there are also aromatic compounds of the non-benzene type ( cm. AROMATICITY). However, they may also contain fragments of saturated or unsaturated hydrocarbon chains (Fig. 18).

Rice. 18. AROMATIC HYDROCARBONS.

There is a group of compounds in which benzene rings seem to be soldered together, these are the so-called condensed aromatic compounds (Fig. 20).

Rice. 20. CONDENSED AROMATIC COMPOUNDS

Many aromatic compounds, including condensed ones (naphthalene and its derivatives), are part of oil, the second source of these compounds is coal tar.

Benzene cycles are not characterized by addition reactions that take place with great difficulty and under harsh conditions; the most typical reactions for them are the substitution reactions of hydrogen atoms (Fig. 21).

Rice. 21. SUBSTITUTION REACTIONS hydrogen atoms in the aromatic nucleus.

In addition to functional groups (halogen, nitro and acetyl groups) attached to the benzene nucleus (Fig. 21), other groups can also be introduced, resulting in the corresponding derivatives of aromatic compounds (Fig. 22), which form large classes of organic compounds - phenols, aromatic amines, etc.

Rice. 22. AROMATIC COMPOUNDS with functional groups. Compounds in which the ne-OH group is attached to a carbon atom in the aromatic nucleus are called phenols, in contrast to aliphatic compounds, where such compounds are called alcohols.

III. HETEROCYCLIC HYDROCARBONS contain in the ring (in addition to carbon atoms) various heteroatoms: O, N, S. Rings can be of various sizes, contain both single and multiple bonds, as well as hydrocarbon substituents attached to the heterocycle. There are options when the heterocycle is "soldered" to the benzene ring (Fig. 24).

Rice. 24. HETEROCYCLIC COMPOUNDS. Their names have developed historically, for example, furan got its name from furan aldehyde furfural, obtained from bran ( lat. furfur bran). For all the compounds shown, the addition reactions are difficult, and the substitution reactions are quite easy. Thus, these are aromatic compounds of the non-benzene type.

The diversity of compounds of this class is further increased due to the fact that a heterocycle can contain two or more heteroatoms per cycle (Fig. 26).

Rice. 26. HETEROCYCLES with two or more heteroatoms.

Just like the previously considered aliphatic, alicyclic and aromatic hydrocarbons, heterocycles can contain various functional groups (-OH, -COOH, -NH 2, etc.), and in some cases the heteroatom in the cycle can also be considered as functional group, since it is able to take part in the corresponding transformations (Fig. 27).

Rice. 27. HETEROATOM N as a functional group. In the name of the last compound, the letter "N" indicates to which atom the methyl group is attached.

Reactions of organic chemistry. In contrast to the reactions of inorganic chemistry, where ions interact at a high rate (sometimes instantaneously), molecules containing covalent bonds usually participate in the reactions of organic compounds. As a result, all interactions proceed much more slowly than in the case of ionic compounds (sometimes tens of hours), often at elevated temperatures and in the presence of substances accelerating the process - catalysts. Many reactions proceed through intermediate stages or in several parallel directions, which leads to a marked decrease in the yield of the desired compound. Therefore, when describing reactions, instead of equations with numerical coefficients (which is traditionally accepted in inorganic chemistry), reaction schemes are often used without specifying stoichiometric ratios.

The name of large classes of organic reactions is often associated with the chemical nature of the active reagent or with the type of organic group introduced into the compound:

a) halogenation introduction of a halogen atom (Fig. 8, first reaction scheme),

b) hydrochlorination, i.e. exposure to HCl (Fig. 8, second reaction scheme)

c) nitration introduction of the NO 2 nitro group (Fig. 21, second direction of the reaction)

d) metallization introduction of a metal atom (Fig. 27, first stage)

a) alkylation introduction of an alkyl group (Fig. 27, second stage)

b) acylation introduction of the acyl group RC(O)- (Fig. 27, second stage)

Sometimes the name of the reaction indicates the features of the rearrangement of the molecule, for example, cyclization ring formation, decyclization ring opening (Fig. 15).

A large class is formed by condensation reactions ( lat. condensatio - compaction, thickening), in which new C-C bonds are formed with the simultaneous formation of easily removed inorganic or organic compounds. Condensation accompanied by the release of water is called dehydration. Condensation processes can also take place intramolecularly, that is, within a single molecule (Fig. 28).

Rice. 28. CONDENSATION REACTIONS

In the condensation of benzene (Fig. 28), the role of functional groups is played by C-H fragments.

The classification of organic reactions is not strict, for example, shown in Fig. 28 The intramolecular condensation of maleic acid can also be attributed to cyclization reactions, and the condensation of benzene to dehydrogenation.

There are intramolecular reactions that are somewhat different from condensation processes, when a fragment (molecule) is split off in the form of an easily removable compound without the obvious participation of functional groups. Such reactions are called elimination ( lat. eliminare expel), while new connections are formed (Fig. 29).

Rice. 29. ELIMINATION REACTIONS

Variants are possible when several types of transformations are jointly realized, which is shown below by the example of a compound in which different types of processes occur upon heating. During thermal condensation of mucic acid (Fig. 30), intramolecular dehydration and subsequent elimination of CO 2 take place.

Rice. thirty. CONVERSION OF MUCKIC ACID(obtained from acorn syrup) into pyromucous acid, so named because it is obtained by heating mucus. Pyrosmucus acid is a heterocyclic compound furan with an attached functional (carboxyl) group. During the reaction, C-O, C-H bonds are broken and new C-H and C-C bonds are formed.

There are reactions in which the rearrangement of the molecule occurs without changing the composition ( cm. ISOMERIZATION).

Research methods in organic chemistry. Modern organic chemistry, in addition to elemental analysis, uses many physical research methods. The most complex mixtures of substances are separated into constituent components using chromatography based on the movement of solutions or vapors of substances through a layer of sorbent. Infrared spectroscopy transmission of infrared (thermal) rays through a solution or through a thin layer of a substance allows you to establish the presence of certain fragments of a molecule in a substance, for example, groups C 6 H 5, C \u003d O, NH 2, etc.

Ultraviolet spectroscopy, also called electronic, carries information about the electronic state of the molecule; it is sensitive to the presence of multiple bonds and aromatic fragments in the substance. Analysis of crystalline substances using X-rays (X-ray diffraction analysis) gives a three-dimensional picture of the arrangement of atoms in a molecule, similar to those shown in the above animated figures, in other words, it allows you to see the structure of the molecule with your own eyes.

The spectral method nuclear magnetic resonance, based on the resonant interaction of the magnetic moments of nuclei with an external magnetic field, makes it possible to distinguish atoms of one element, for example, hydrogen, located in different fragments of the molecule (in the hydrocarbon skeleton, in the hydroxyl, carboxyl or amino group), as well as determine their proportion. A similar analysis is also possible for the nuclei C, N, F, etc. All these modern physical methods have led to intensive research in organic chemistry - it has become possible to quickly solve those problems that previously took many years.

Some sections of organic chemistry have emerged as large independent areas, for example, the chemistry of natural substances, drugs, dyes, and the chemistry of polymers. In the middle of the 20th century the chemistry of organoelement compounds began to develop as an independent discipline that studies substances containing a S-E bond, where the symbol E denotes any element (except carbon, hydrogen, oxygen, nitrogen and halogens). Great progress has been made in biochemistry, which studies the synthesis and transformations of organic substances occurring in living organisms. The development of all these areas is based on the general laws of organic chemistry.

Modern industrial organic synthesis includes a wide range of different processes these are, first of all, large-scale production oil and gas processing and the production of motor fuels, solvents, coolants, lubricating oils, in addition, the synthesis of polymers, synthetic fibers, various resins for coatings, adhesives and enamels. Small-tonnage industries include the production of medicines, vitamins, dyes, food additives and fragrances.

Mikhail Levitsky

LITERATURE Karrer P. Organic chemistry course, per. from German, GNTI Himlit, L., 1962
Cram D, Hammond J. Organic chemistry, per. from English, Mir, M., 1964

Organic chemistry - it is the science of carbon-containing compounds and ways of their synthesis. Since the variety of organic substances and their transformations is unusually large, the study of this major branch of science requires a special approach.

If you have any uncertainty about the possibility of successfully mastering the subject, do not worry! 🙂 Below are some tips to help you dispel those fears and succeed!

• Generalizing schemes

Record all chemical transformations that you encounter when studying a particular class of organic compounds in summary diagrams. You can draw them to your liking. These schemes, in which the main reactions are collected, will serve as guides for you to easily find ways to transform one substance into another. Schemes can be hung near your workplace to catch the eye more often, so it's easier to remember them. It is possible to draw up one large scheme containing all classes of organic compounds. For example, these: or this scheme:

The arrows must be numbered and below (under the diagram) give examples of reactions and conditions. Several reactions are possible, leave a lot of space in advance. The volume will be large, but it will help you a lot in solving tasks 32 USE in chemistry "Reactions confirming the relationship of organic compounds" (former C3).

• Review cards

When studying organic chemistry, it is necessary to learn a large number of chemical reactions, you will have to remember and understand how many transformations proceed. Special cards can help you with this.

Get a pack of cards about 8 X 12 cm in size. Write the reagents on one side of the card, and the reaction products on the other:

You can carry these cards with you and view them several times a day. It is more useful to refer to the cards several times for 5-10 minutes than once, but for a long period of time.

When a lot of such cards are typed, they should be divided into two groups:

group number 1 - those that you know well, you look through them once every 1-2 weeks, and

group number 2 - those that cause difficulties, you look through them every day until they “pump over” to group number 1.

This method can also be used to learn a foreign language, on one side of the card you write a word, on the back of its translation, so you can quickly replenish your vocabulary. In some language courses, such cards are issued ready-made. So, this is a proven method!

• pivot table

This table needs to be rewritten or printed (copying is available after authorization on the site), if the reaction is not typical for this connection class, then put a minus, and if it is typical, then a plus sign and a number in order, and write examples corresponding to the numbering below the table. This is also a very good way to systematize knowledge of organics!

• Constant repetition

Organic chemistry, like a foreign language, is a cumulative discipline. The material that follows builds on what has been learned so far. Therefore, return periodically to the topics covered.

• Molecule models

Since the shape and geometry of molecules are of great importance in organic chemistry, it is a good idea for a student to have a set of molecular models. Such models, which can be held in the hands, will assist in the study of the stereochemical characteristics of molecules.

Remember that attention to new words and terms is just as important in organic chemistry as it is in other disciplines. Keep in mind that reading non-fiction is always slower than reading fiction. Don't try to cover everything quickly. In order to understand the material presented well, slow, thoughtful reading is necessary. You can read it twice: the first time for a cursory review, the second for a closer study.

Good luck! You will succeed!

If you entered the university, but by this time you have not figured out this difficult science, we are ready to reveal a few secrets to you and help you learn organic chemistry from scratch (for "dummies"). You just have to read and listen.

Fundamentals of organic chemistry

Organic chemistry is singled out as a separate subspecies due to the fact that the object of its study is everything that contains carbon.

Organic chemistry is a branch of chemistry that deals with the study of carbon compounds, the structure of such compounds, their properties and methods of connection.

As it turned out, carbon most often forms compounds with the following elements - H, N, O, S, P. By the way, these elements are called organogens.

Organic compounds, the number of which today reaches 20 million, are very important for the full existence of all living organisms. However, no one doubted, otherwise a person would simply have thrown the study of this unknown into the back burner.

The goals, methods and theoretical concepts of organic chemistry are presented as follows:

• Separation of fossil, animal or vegetable raw materials into separate substances;
• Purification and synthesis of various compounds;
• Revealing the structure of substances;
• Determination of the mechanics of the course of chemical reactions;
• Finding the relationship between the structure and properties of organic substances.

A bit from the history of organic chemistry

You may not believe it, but even in ancient times, the inhabitants of Rome and Egypt understood something in chemistry.

As we know, they used natural dyes. And often they had to use not a ready-made natural dye, but extract it by isolating it from a whole plant (for example, alizarin and indigo contained in plants).

We can also remember the culture of drinking alcohol. The secrets of the production of alcoholic beverages are known in every nation. Moreover, many ancient peoples knew the recipes for preparing "hot water" from starch- and sugar-containing products.

This went on for many, many years, and only in the 16th and 17th centuries did some changes, small discoveries, begin.

In the 18th century, a certain Scheele learned to isolate malic, tartaric, oxalic, lactic, gallic and citric acids.

Then it became clear to everyone that the products that could be isolated from plant or animal raw materials had many common features. At the same time, they differed greatly from inorganic compounds. Therefore, the servants of science urgently needed to separate them into a separate class, and the term “organic chemistry” appeared.

Despite the fact that organic chemistry itself as a science appeared only in 1828 (it was then that Mr. Wöhler managed to isolate urea by evaporating ammonium cyanate), in 1807 Berzelius introduced the first term in the nomenclature in organic chemistry for teapots:

Branch of chemistry that studies substances derived from organisms.

The next important step in the development of organic chemistry is the theory of valence, proposed in 1857 by Kekule and Cooper, and the theory of the chemical structure of Mr. Butlerov from 1861. Even then, scientists began to discover that carbon is tetravalent and is able to form chains.

In general, since then, science has regularly experienced upheavals and unrest due to new theories, discoveries of chains and compounds, which allowed organic chemistry to also actively develop.

Science itself appeared due to the fact that scientific and technological progress was not able to stand still. He kept on walking, demanding new solutions. And when coal tar was no longer enough in the industry, people simply had to create a new organic synthesis, which eventually grew into the discovery of an incredibly important substance, which is still more expensive than gold - oil. By the way, it was thanks to organic chemistry that her "daughter" was born - a subscience, which was called "petrochemistry".

But this is a completely different story that you can study for yourself. Next, we suggest you watch a popular science video about organic chemistry for dummies:

Well, if you have no time and urgently need help professionals, you always know where to find them.

SIBERIAN POLYTECHNICAL COLLEGE

STUDENT HANDBOOK

in ORGANIC CHEMISTRY

for specialties of technical and economic profiles

Compiled by: teacher

2012

Structure "STUDENT'S HANDBOOK on ORGANIC CHEMISTRY"

EXPLANATORY NOTE

The SS in organic chemistry is designed to assist students in creating a scientific picture of the world through chemical content, taking into account interdisciplinary and intradisciplinary connections, the logic of the educational process.

The SS in organic chemistry presents the minimum in terms of volume, but functionally complete content for the development of the state standard chemical education.

The CC in Organic Chemistry performs two main functions:

I. The information function allows participants in the educational process to get an idea of ​​the content, structure of the subject, the relationship of concepts through diagrams, tables and algorithms.

II. The organizational and planning function provides for the allocation of training stages, the structuring of educational material, and creates ideas about the content of the intermediate and final certification.

SS involves the formation of a system of knowledge, skills and methods of activity, develops the ability of students to work with reference materials.

	Name		Name
	Chronological table "Development of organic chemistry".		Chemical properties of alkenes (ethylene hydrocarbons).
	The main provisions of the theory of the structure of organic compounds		Chemical properties of alkynes (acetylenic hydrocarbons).
	Isomers and homologues.		Chemical properties of arenes (aromatic hydrocarbons).
	TSOS value
	Classification of hydrocarbons.		Genetic connection of organic substances.
	homologous series ALKANE (LIMITED HYDROCARBONS).		Relationship "Structure - properties - application".
	homologous series RADICALS FORMATED FROM ALKANE.		Relative molecular weights of organic substances
			Dictionary of terms in organic chemistry. nominal reactions.
	Isomerism of classes of organic substances.		Algorithm for solving problems. Physical quantities for solving problems.
	Chemical properties of alkanes (saturated hydrocarbons).		Derivation of compound formulas. Examples of problem solving.

CHRONOLOGICAL TABLE "DEVELOPMENT OF ORGANIC CHEMISTRY"

Period/year. Who?	The nature of the discovery
Ancient Shih	ancient man	Boil food, tan leather, make medicine
	Paracelsus and others	The manufacture of more complex drugs, the study of the properties of substances org. origin, i.e. waste products
XY-XYIII c. V.	Continuous process	Accumulation of knowledge about various substances. The supremacy of "VITALISTIC VIEWS"
		An explosion of scientific thought, the detonator of which was the needs of people for dyes, clothes, food.
	Jöns Jakob Berzelius (Swedish chemist)	The term "organic chemistry"
	Friedrich Wöhler (German)	Synthesis of oxalic acid
	concept	Organic chemistry is a branch of chemical science that studies carbon compounds.
	Friedrich Wöhler (German)	Urea synthesis
		Synthesis of aniline
	Adolf Kulbe (German)	Synthesis of acetic acid from carbon
	E. Frankland	The concept of "connecting system" - valency
	Pierre Berthelot (French)	Synthesized ethyl alcohol by hydration of ethylene. Synthesis of fats. "Chemistry doesn't need life force!"
		Synthesis of a sugar substance
		Based on various theories (Frankland, Gerard, Kekule, Cooper) created TSOS
		Textbook "Introduction to the Complete Study of Organic Chemistry". Organic chemistry is the branch of chemistry that studies hydrocarbons and their derivatives. .

MAIN PROVISIONS

THEORIES OF THE STRUCTURE OF ORGANIC COMPOUNDS

A. M. Butlerova

1. A. in M. are connected in a certain sequence, according to their valency.

2. The properties of substances depend not only on the qualitative and quantitative composition, but also on the chemical structure. Isomers. Isomerism.

3. A. and A. groups mutually influence each other.

4. By the properties of a substance, you can determine the structure, and by the structure - properties.

Isomers and homologues.

	Qualitative composition	Quantitative composition	Chemical structure	Chemical properties
Isomers	same	same	various	various
homologues	same	different	similar	similar

TSOS value

1. Explained the structure of M. known substances and their properties.

2. Made it possible to foresee the existence of unknown substances and find ways to synthesize them.

3. Explain the diversity of organic substances.

Classification of hydrocarbons.

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homologous series

ALKANE (LIMITED HYDROCARBONS)

Formula	Name
	METHANE
C2H6	ETHANE
С3Н8	PROPANE
	BUTANE
	PENTAN
	HEXANE
	HEPTANE
	OCTANE
	NONAN
С10Н22	DEAN

homologous series

RADICALS FORMATED FROM ALKANE

Formula	Name
	METHYL
C2H5	ETHYL
С3Н7	PROPIL
	BUTYL
	PENTIL
	HEKSIL
	GEPTIL
	OKTIL
	NONIL
C10H21	DECYL

General information about hydrocarbons.

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Chemical properties of alkanes

(saturated hydrocarbons).

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Chemical properties of alkynes

(acetylenic hydrocarbons).

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Genetic link between hydrocarbons.

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Relationship "Structure - properties - application".	Ways receiving
	Structure
Compound		Finding in nature
	Properties	Application

MOLECULAR WEIGHTS OF SOME ORGANIC SUBSTANCES.

Name
Alkanes
Halogen derivatives
Alcohols and Phenols
Ethers
Aldehydes
carboxylic acids
Nitro compounds

Problem solving algorithm

1. Study the conditions of the problem carefully: determine with what quantities the calculations are to be carried out, designate them with letters, set their units of measurement, numerical values, determine which value is the desired one.

2. Write down these tasks in the form of brief conditions.

3. If in the conditions of the problem we are talking about the interaction of substances, write down the equation of the reaction (reactions) and equalize it (their) coefficients.

4. Find out the quantitative relationships between the data of the problem and the desired value. To do this, divide your actions into stages, starting with the question of the problem, finding out the patterns with which you can determine the desired value at the last stage of calculations. If the initial data lacks any values, think about how they can be calculated, i.e., determine the preliminary stages of the calculation. There may be several of these steps.

5. Determine the sequence of all stages of solving the problem, write down the necessary calculation formulas.

6. Substitute the corresponding numerical values ​​of the quantities, check their dimensions, and perform calculations.

Derivation of compound formulas.

This type of calculation is extremely important for chemical practice, since it allows, on the basis of experimental data, to determine the formula of a substance (simple and molecular).

Based on the data of qualitative and quantitative analyzes, the chemist first finds the ratio of atoms in a molecule (or other structural unit of a substance), that is, its simplest formula.
For example, the analysis showed that the substance is a hydrocarbon
CxHy, in which the mass fractions of carbon and hydrogen are respectively equal to 0.8 and 0.2 (80% and 20%). To determine the ratio of atoms of elements, it is enough to determine their amounts of matter (number of moles): Integer numbers (1 and 3) are obtained by dividing the number 0.2 by the number 0.0666. The number 0.0666 will be taken as 1. The number 0.2 is 3 times greater than the number 0.0666. So CH3 is the simplest the formula for this substance. The ratio of C and H atoms, equal to 1:3, corresponds to an innumerable number of formulas: C2H6, C3H9, C4H12, etc., but only one formula from this series is molecular for a given substance, i.e., reflecting the true number of atoms in its molecule. To calculate the molecular formula, in addition to the quantitative composition of a substance, it is necessary to know its molecular weight.

To determine this value, the relative gas density D is often used. So, for the above case, DH2 = 15. Then M(CxHy) = 15µM(H2) = 152 g/mol = 30 g/mol.
Since M(CH3) = 15, it is necessary to double the indices in the formula to match the true molecular weight. Hence, molecular substance formula: C2H6.

The definition of the formula of a substance depends on the accuracy of mathematical calculations.

When finding a value n element should take into account at least two decimal places and carefully round numbers.

For example, 0.8878 ≈ 0.89, but not 1. The ratio of atoms in a molecule is not always determined by simply dividing the resulting numbers by a smaller number.

by mass fractions of elements.

Task 1. Set the formula of a substance that consists of carbon (w=25%) and aluminum (w=75%).

Divide 2.08 by 2. The resulting number 1.04 does not fit an integer number of times in the number 2.78 (2.78:1.04=2.67:1).

Now let's divide 2.08 by 3.

In this case, the number 0.69 is obtained, which fits exactly 4 times in the number 2.78 and 3 times in the number 2.08.

Therefore, the x and y indices in the AlxCy formula are 4 and 3, respectively.

Answer: Al4C3(aluminum carbide).

Algorithm for finding the chemical formula of a substance

by its density and mass fractions of elements.

A more complex version of the tasks for deriving formulas of compounds is the case when the composition of a substance is given through the combustion products of these.

Task 2. When burning a hydrocarbon weighing 8.316 g, 26.4 g of CO2 was formed. The density of the substance under normal conditions is 1.875 g / ml. Find its molecular formula.

General information about hydrocarbons.

(continuation)

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Natural sources of hydrocarbons.

Oil - fossil, liquid fuel, a complex mixture of organic substances: saturated hydrocarbons, paraffins, naphthenes, aromatics, etc. Oil usually contains oxygen-, sulfur- and nitrogen-containing substances.

Oily liquid with a characteristic odor, dark in color, lighter than water. The most important source of fuel, lubricating oils and other petroleum products. The main (primary) processing process is distillation, as a result of which gasoline, naphtha, kerosene, solar oils, fuel oil, petroleum jelly, paraffin, and tar are obtained. Secondary recycling processes ( cracking, pyrolysis) make it possible to obtain additional liquid fuel, aromatic hydrocarbons (benzene, toluene, etc.), etc.

Petroleum gases - a mixture of various gaseous hydrocarbons dissolved in oil; they are released during extraction and processing. They are used as fuel and chemical raw materials.

Petrol- a colorless or yellowish liquid, consists of a mixture of hydrocarbons ( C5 - C11 ). It is used as motor fuel, solvent, etc.

Naphtha- transparent yellowish liquid, a mixture of liquid hydrocarbons. It is used as diesel fuel, solvent, hydraulic fluid, etc.

Kerosene- transparent, colorless or yellowish liquid with a blue tint. It is used as a fuel for jet engines, for household needs, etc.

Solar- a yellowish liquid. It is used for the production of lubricating oils.

fuel oil– heavy oil fuel, a mixture of paraffins. They are used in the production of oils, fuel oil, bitumen, for processing into light motor fuel.

Benzene It is a colorless liquid with a characteristic odour. It is used for the synthesis of organic compounds, as a raw material for the production of plastics, as a solvent, for the production of explosives, in the aniline-dye industry.

Toluene is an analogue of benzene. It is used in the production of caprolactam, explosives, benzoic acid, saccharin, as a solvent, in the aniline-dye industry, etc.

Lubricating oils- Used in various fields of technology to reduce friction fur. parts, to protect metals from corrosion, as a cutting fluid.

Tar- black resinous mass. Used for lubrication, etc.

Petrolatum- a mixture of mineral oil and paraffins. They are used in electrical engineering, for lubricating bearings, for protecting metals from corrosion, etc.

Paraffin- a mixture of solid saturated hydrocarbons. Used as an electrical insulator, in chem. industry - to obtain higher acids and alcohols, etc.

Plastic– materials based on macromolecular compounds. Used for the production of various technical products and household items.

asphalt ore- a mixture of oxidized hydrocarbons. It is used for the manufacture of varnishes, in electrical engineering, for asphalting streets.

mountain wax- a mineral from the group of petroleum bitumens. It is used as an electrical insulator, for the preparation of various lubricants and ointments, etc.

artificial wax- purified mountain wax.

Coal - solid fossil fuel of plant origin, black or black-gray. Contains 75–97% carbon. Used as a fuel and as a raw material for the chemical industry.

Coke- a sintered solid product formed when certain coals are heated in coke ovens to 900–1050° C. Used in blast furnaces.

coke oven gas– gaseous products of coking of fossil coals. Comprises CH4, H2, CO and others, also contains non-combustible impurities. It is used as a high-calorie fuel.

ammonia water- liquid product of dry distillation of coal. It is used to obtain ammonium salts (nitrogen fertilizers), ammonia, etc.

Coal tar- a thick dark liquid with a characteristic odor, a product of the dry distillation of coal. It is used as a raw material for chemical industry.

Benzene- a colorless mobile liquid with a characteristic odor, one of the products of coal tar. They are used for the synthesis of organic compounds, as explosives, as a raw material for the production of plastics, as a dye, as a solvent, etc.

Naphthalene- a solid crystalline substance with a characteristic odor, one of the products of coal tar. Naphthalene derivatives are used to obtain dyes and explosives, etc.

Medications- the coke industry produces a number of drugs (carbolic acid, phenacytin, salicylic acid, saccharin, etc.).

Pitch- a solid (viscous) mass of black color, the residue from the distillation of coal tar. It is used as a waterproofing agent, for the production of fuel briquettes, etc.

Toluene- analogue of benzene, one of the products of coal tar. Used for the production of explosives, caprolactam, benzoic acid, saccharin, as a dye, etc.

Dyes- one of the products of coke production, obtained as a result of the processing of benzene, naphthalene and phenol. Used in the national economy.

Aniline- colorless oily liquid, poisonous. It is used to obtain various organic substances, aniline dyes, various azo dyes, the synthesis of drugs, etc.

Saccharin- solid white crystalline substance of sweet taste, obtained from toluene. It is used instead of sugar for diabetes, etc.

BB- derivatives of coal obtained in the process of dry distillation. They are used in the military industry, mining and other sectors of the national economy.

Phenol- a crystalline substance of white or pink color with a characteristic strong odor. It is used in the production of phenol-formaldehyde plastics, nylon synthetic fiber, dyes, medicines, etc.

Plastic– materials based on macromolecular compounds. Used for the production of various technical products and household items.