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Pomogaev A.I.

Short Course in Organic Chemistry Part 1

Theoretical Foundations of Organic Chemistry.

Textbook M., MITHT them. M.V. Lomonosov, 2003 - 48 p.

Edition 2nd.

Approved by the MITHT Library and Publishing Commission

them. M.V. Lomonosov as a teaching aid.

Given Toolkit is intended for 3rd year students of the undergraduate direction "Materials Science and Technology of New Materials", studying organic chemistry during one academic semester.

The manual is a presentation of material that does not go mainly beyond curriculum in organic chemistry for this direction. At the end of each section are exercises and typical tasks independent decision which will help the student to prepare for control work as well as for the exam.

Prepared at the Department of Organic Chemistry MITHT them. M.V. Lomonosov.

© Moscow State Academy Fine Chemical Technology them. M.V. Lomonosov

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STRUCTURE OF ORGANIC COMPOUNDS _____________ 4

1. Classification organic compounds ____________________________4

2. Formation of bonds in organic compounds ______________________ 5

3. Properties of covalent bonds ____________________________________________9

4. Electronic displacements in molecules of organic compounds _________11

4.1. Inductive effect _____________________________________________11

4.2. Orbital conjugation: bond delocalization, mesomeric effect ______14

5. Isomerism of organic compounds________________________________19

5.1. Structural isomerism ____________________________________________19

5.2. Stereoisomerism __________________________________________________20

6. Tasks and exercises _____________________________________________32

FOUNDATIONS OF THE THEORY OF ORGANIC REACTIONS __________ 34

1. Classification of organic reactions according to the type of bond rupture __________34

1.1. Homolytic or free radical reactions ___________________34

1.2. Heterolytic or ionic reactions ______________________________36

2. Classification of reactions according to the type of transformation _______________________38

3. Acids and bases in organic chemistry _________________________39

3.1. Bronsted acids and bases __________________________________________39

3.2. Lewis acids and bases ____________________________________________43

3.3. Acid-base catalysis____________________________________________44

4. Tasks and exercises _____________________________________________45

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STRUCTURE OF ORGANIC COMPOUNDS

1. Classification of organic compounds

Organic chemistry studies various compounds of carbon,

the simplest of which are compounds of carbon with hydrogen -

hydrocarbons. All other organic substances can be considered as hydrocarbon derivatives, which differ from hydrocarbons in that in them one or more hydrogen atoms are replaced by some other atoms or groups of atoms (functional groups).

The composition of organic compounds, in addition to carbon and hydrogen atoms, may include atoms of other elements (the so-called heteroatoms). This,

first of all, halogen atoms (halogen derivatives of hydrocarbons),

oxygen (alcohols, phenols, ethers, aldehydes, ketones, carboxylic acids), nitrogen (amines, nitro compounds), sulfur (thiols, sulfonic acids),

metals (organometallic compounds) and many other elements.

IN The classification of organic compounds is based on their structure

– sequence of atoms in a molecule. To classify organic compounds, the hydrocarbon base (parent structure) is first classified, referring it to saturated hydrocarbons with an open chain or cyclic, saturated or unsaturated,

alicyclic or aromatic. And then they are assigned to the corresponding derivatives of hydrocarbons, considering the functional group. So, for example, butane is a saturated non-cyclic hydrocarbon (such hydrocarbons are called alkanes), 1-butene is an unsaturated non-cyclic hydrocarbon having a double bond (alkene). Cyclobutene is a cyclic alkene and benzene is an aromatic hydrocarbon. 2-Butenal is unsaturated acyclic

(i.e., non-cyclic) aldehyde, and benzoic acid is an aromatic carboxylic acid.

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CH3 CH2 CH2 CH3	CH2 =CHCH2 CH3		CH3CH=CHCH=O
		cyclobutene	2-butenal	benzoic

2. Formation of bonds in organic compounds

The molecule of any organic compound is an ordered collection of atoms connected predominantly by a covalent bond. Ionic bond also occurs in organic molecules, however, it does not determine the structure and chemical behavior of the vast majority of organic compounds. Organic chemistry is the chemistry of covalent compounds of carbon.

covalent bond- this is a bond that two atoms carry out through a socialized pair of electrons. The socialization of a pair of electrons occurs when overlapping atomic orbitals two atoms, while it is completely indifferent (for the resulting bond) how many electrons were in each of the overlapping orbitals. Both orbitals can have one electron each, or one of the orbitals can have a pair of electrons, and the other can not have a single electron (in the latter case, they speak of a donor-acceptor mechanism for the formation of a covalent bond).

The orbitals that the atoms of the elements of the 1st and 2nd periods provide for the formation of bonds in organic compounds can have the usual characteristics for atomic orbitals, i.e., be s-or p-orbitals. So,

for example, in the formation of a hydrogen chloride molecule, the chlorine atom provides the p-orbital, and the hydrogen atom provides the s-orbital. There can be one electron in the p-orbital of the chlorine atom, then the hydrogen atom also provides one electron to form a bond. Or there can be two electrons (anion) on the p-orbital of the chlorine atom, then to form a bond, the hydrogen atom must have an empty, or vacant, orbital (proton). In the latter case, the covalent bond is formed by the donor-acceptor method: the chlorine anion acts as an electron pair donor, and the proton as its acceptor. Below

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two schemes of education are presented molecular orbitals(binding and anti-bonding, or loosening) when interacting (overlapping)

atomic orbitals.

For the carbon atom, as for the atoms of other elements of the second period,

which can form both simple (single) bonds and double or triple bonds, the so-called hybridization of atomic orbitals is characteristic,

when atomic orbitals of different energies (s- and p-orbitals) align their energies, forming the so-called degenerate orbitals, i.e. orbitals,

having the same energy.

A carbon atom has four electrons in its outer energy level. Two valence electrons are located on the s-orbital, on two p-

orbitals have one electron each, and the third p-orbital is empty. When bonds are formed, the carbon atom is excited, and one of the s-electrons goes to the vacant p-orbital.

excitation

s px ru pz

An excited carbon atom with the electronic configuration 2s2p3 can form a maximum of four covalent bonds. In this case, bonds can be formed with a different number of atoms - with four, three or two.

In the first case, when the carbon atom forms bonds with four neighboring atoms, i.e. is four-coordination, hybridization of all four orbitals occurs with the formation of four degenerate orbitals that differ from the original orbitals both in energy and in shape.

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This process, according to the orbitals involved in the process, is called sp 3 -

hybridization, and the resulting orbitals are sp3-hybrid orbitals. In space, these hybrid orbitals lie on the axes

as far as possible from each other and located because of this at an angle

109.50 to each other (as segments connecting the center of the tetrahedron with its vertices). Therefore, the carbon atom in sp3 hybridization is also called

tetrahedral.

		109.5o

When a carbon atom forms bonds with three neighboring atoms, i.e.

is tri-coordinate, the energies of three orbitals are aligned - one s- and two p-orbitals with the formation of three degenerate sp 2 -hybrid orbitals, the axes of which lie in the same plane at an angle of 120O

to each other. The p-orbital not participating in hybridization is located perpendicular to the said plane.

		120o
		sp2

In the third case, when the carbon atom is bi-coordinate And

is bound to only two neighboring atoms, sp-hybridization is realized. Two degenerate sp-orbitals are located at an angle of 180° to each other, i.e. on one coordinate axis, and two non-hybrid p-orbitals are on the other two

coordinate axes.

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The formation of bonds of a carbon atom occurs when its hybrid orbitals overlap with the corresponding hybrid or non-hybrid orbitals of other atoms. In this case, two fundamentally different ways of overlapping orbitals can be implemented.

A) Axial overlap of orbitals , at which the overlap maximum is on the axis passing through the nuclei of the binding atoms, leads to the formationσ-bonds. The electron density of this bond lies between the nuclei of the bound atoms. It is symmetrical about the overlap axis.σ-bond can be formed by overlapping any atomic orbitals. Hydrogen and chlorine atoms in a hydrogen chloride molecule are bondedσ-bond, formed as a result of axial overlap s-orbitals a hydrogen atom and p-orbitals chlorine atom. In the methane molecule, all four bonds between the carbon atom and the hydrogen atoms are alsoσ-bonds, each of which is formed by overlapping one of the four sp 3 -hybrid orbitals of a carbon atom with s-orbital of the hydrogen atom.

Overlapping of atomic orbitals during the formation of σ-bonds in molecules of hydrogen chloride (a) and methane (b)

B) Lateral overlap of orbitals is the overlap of two p-

orbitals located on mutually parallel axes. The π-bond formed during such an overlap is characterized by the fact that the maximum of the overlap is not located on the axis passing through the nuclei of the bound atoms. The π-bond is formed by p-orbitals of sp2- or sp-hybridized atoms.

So, for example, in an ethylene molecule (CH2 \u003d CH2), three sp2 hybrid orbitals of each carbon atom with axial overlap with two s-

orbitals of hydrogen atoms and one sp2 orbital of the neighboring carbon atom

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form three σ-bonds. Non-hybrid p-orbitals of carbon atoms overlap "sideways" and form a π-bond. In this case, all five σ-bonds are located in the same plane, and the symmetry plane of the π-bond is perpendicular to it.

In the acetylene molecule, the carbon-carbon triple bond is a combination of a σ bond and two π bonds. The latter are formed by lateral overlap of non-hybrid p-orbitals in mutually perpendicular

planes.

Formation of π-bonds in ethylene (a) and acetylene (b) molecules

3. Properties of covalent bonds

A covalent bond is characterized by the following parameters:

 Bond length is defined as the distance between bonded atoms. The bond length depends on the radii of the bonded atoms, on the type of hybridization of the atoms,

and also on the multiplicity of the connection (Table 1).

							Table 1
			Bond length, Å				Bond length, Å

 Bond energy is defined as the energy of formation or dissociation of a bond and depends on the nature of the bonded atoms, on the length of the bond, as well as on its

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multiplicity (Table 2). It should be noted that the energy of a double C-C bond does not represent twice the energy of a simple one, since the lateral overlap of orbitals is less efficient than the axial one, and, therefore, π-

the bond is less strong than the σ-bond.

						table 2
	Communication type			bond energy,	Communication type	bond energy,
				kcal/mol		kcal/mol

 Communication polarity is determined by the difference in the electronegativity of the bonded atoms. The electronegativity of an atom is its ability to attract valence electrons. If the electronegativity of the bonded atoms is the same, the electron density of the bond is evenly distributed between the atoms. In all other cases, the electron density of the bond is shifted in one direction or another, depending on which of the atoms it is attracted to more strongly. In this case, a so-called partial negative charge arises on a more electronegative atom, and a partial positive charge arises on a less electronegative atom. For diatomic molecules, the polarity of the bond can be very simply characterized by the dipole moment of the molecule, which can be measured. Normally, the polarity of a single bond is represented by an arrow along the bond towards the more electronegative atom. The polarity of multiple bonds is represented by a curved arrow pointing from the bond to the more electronegative atom. The following are examples

From all the variety chemical compounds most (over four million) contains carbon. Almost all of them are organic. Organic compounds are found in nature, such as carbohydrates, proteins, vitamins, they play important role in the life of animals and plants. Many organic substances and their mixtures (plastics, rubber, oil, natural gas, and others) are of great importance for the development National economy countries.

The chemistry of carbon compounds is called organic chemistry. This is how the great Russian organic chemist A.M. Butlerov. However, not all carbon compounds are usually classified as organic. Such simple substances as carbon monoxide (II) CO, carbon dioxide CO2, carbonic acid H2CO3 and its salts, for example, CaCO3, K2CO3, are classified as inorganic compounds. Part organic matter besides carbon, other elements can also be included. The most common are hydrogen, halogens, oxygen, nitrogen, sulfur and phosphorus. There are also organic substances containing other elements, including metals.

2. The structure of the carbon atom (C), the structure of its electron shell

2.1 The value of the carbon atom (C) in the chemical structure of organic compounds

CARBON (lat. Carboneum), C, chemical element of subgroup IVa periodic system; atomic number 6, atomic mass 12.0107 refers to non-metals. Natural carbon consists of two stable nuclides - 12C (98.892% by mass) and 13C (1.108%) and one unstable - C with a half-life of 5730 years.

distribution in nature. Carbon accounts for 0.48% by weight earth's crust, in which it occupies the 17th place among other elements in terms of content. The main carbon-bearing rocks are natural carbonates (limestones and dolomites); the amount of carbon in them is about 9.610 tons.

In the free state, carbon occurs in nature in the form of fossil fuels, as well as in the form of minerals - diamond and graphite. About 1013 tons of carbon is concentrated in fossil fuels such as hard and brown coal, peat, shale, bitumen, which form powerful accumulations in the bowels of the Earth, as well as in natural combustible gases. Diamonds are extremely rare. Even diamond-bearing rocks (kimberlites) contain no more than 9-10% of diamonds weighing, as a rule, no more than 0.4 g. Large diamonds found are usually given a special name. The largest Cullinan diamond weighing 621.2 g (3106 carats) was found in South Africa (Transvaal) in 1905, and the largest Russian Orlov diamond weighing 37.92 g (190 carats) was found in Siberia in the middle 17th century

Black-gray opaque, greasy to the touch with a metallic sheen, graphite is an accumulation of flat polymeric molecules of carbon atoms, loosely layered on top of each other. In this case, the atoms within the layer are more strongly interconnected than the atoms between the layers.

Diamond is another matter. In its colorless, transparent and highly refractive crystal, each carbon atom is chemically bonded to four of the same atoms located at the vertices of the tetrahedron. All bonds are the same length and are very strong. They form a continuous three-dimensional frame in space. The entire diamond crystal is, as it were, one giant polymer molecule that has no "weak" places, because the strength of all bonds is the same.

The density of diamond at 20°C is 3.51 g/cm 3 , graphite - 2.26 g/cm 3 . The physical properties of diamond (hardness, electrical conductivity, coefficient of thermal expansion) are practically the same in all directions; it is the hardest of all substances found in nature. In graphite, these properties in different directions - perpendicular or parallel to the layers of carbon atoms - differ greatly: with small lateral forces, the parallel layers of graphite shift relative to each other and it delaminates into separate flakes that leave a mark on the paper. By electrical properties diamond is a dielectric, while graphite conducts electricity.

Diamond, when heated without air access above 1000 ° C, turns into graphite. Graphite under constant heating under the same conditions does not change up to 3000 ° C, when it sublimates without melting. The direct transition of graphite to diamond occurs only at temperatures above 3000°C and enormous pressure - about 12 GPa.

The third allotropic modification of carbon - carbine - was obtained artificially. It is a finely crystalline black powder; in its structure, long chains of carbon atoms are parallel to each other. Each chain has the structure of (-C=C) L or (=C=C=) L. The average density of carbine between graphite and diamond is 2.68-3.30 g/cm 3 . One of the most important features of carbine is its compatibility with the tissues of the human body, which allows it to be used, for example, in the manufacture of artificial blood vessels that are not rejected by the body (Fig. 1).

Fullerenes got their name not in honor of the chemist, but in honor of the American architect R. Fuller, who proposed building hangars and other structures in the form of domes, the surface of which is formed by pentagons and hexagons (such a dome was built, for example, in Moscow's Sokolniki Park).

Carbon is also characterized by a state with a disordered structure - this is the so-called. amorphous carbon (soot, coke, charcoal) fig. 2. Obtaining carbon (C):

Most of the substances around us are organic compounds. These are the tissues of animals and plants, our food, medicines, clothing (cotton, wool and synthetic fibers), fuels (oil and natural gas), rubber and plastics, detergents. Currently, more than 10 million such substances are known, and their number increases significantly every year due to the fact that scientists isolate unknown substances from natural objects and create new compounds that do not exist in nature.

Such a variety of organic compounds is associated with the unique feature of carbon atoms to form strong covalent bonds, both among themselves and with other atoms. Carbon atoms, connecting to each other with both single and multiple bonds, can form chains of almost any length and cycles. A wide variety of organic compounds is also associated with the existence of the phenomenon of isomerism.

Almost all organic compounds also contain hydrogen, often they include atoms of oxygen, nitrogen, less often - sulfur, phosphorus, halogens. Compounds containing atoms of any elements (with the exception of O, N, S and halogens) directly bonded to carbon are grouped under the name organoelement compounds; the main group of such compounds is organometallic compounds (Fig. 3).

A huge number of organic compounds require their clear classification. The basis of an organic compound is the skeleton of a molecule. The skeleton can have an open (non-closed) structure, then the compound is called acyclic (aliphatic; aliphatic compounds are also called fatty compounds, since they were first isolated from fats), and a closed structure, then it is called cyclic. The skeleton can be carbon (consist only of carbon atoms) or contain other atoms other than carbon - the so-called. heteroatoms, most often oxygen, nitrogen and sulfur. Cyclic compounds are divided into carbocyclic (carbon), which can be aromatic and alicyclic (containing one or more rings), and heterocyclic.

Hydrogen and halogen atoms are not included in the skeleton, and heteroatoms are included in the skeleton only if they have at least two carbon bonds. So, in ethyl alcohol CH3CH2OH, the oxygen atom is not included in the skeleton of the molecule, but in dimethyl ether CH3OCH3 is included in it.

In addition, the acyclic skeleton can be unbranched (all atoms are arranged in one row) and branched. Sometimes an unbranched skeleton is called linear, but it should be remembered that structural formulas, which we most often use, convey only the order of the bond, and not the actual arrangement of the atoms. Thus, a "linear" carbon chain has a zigzag shape and can twist in space in various ways.

There are four types of carbon atoms in the skeleton of a molecule. A carbon atom is called primary if it forms only one bond with another carbon atom. The secondary atom is bonded to two other carbon atoms, the tertiary atom to three, and the quaternary uses all four of its bonds to form bonds with carbon atoms.

The next classification feature is the presence of multiple bonds. Organic compounds containing only simple bonds are called saturated (limiting). Compounds containing double or triple bonds are called unsaturated (unsaturated). In their molecules, there are fewer hydrogen atoms per carbon atom than in the limiting ones. Cyclic unsaturated hydrocarbons of the benzene series are isolated into a separate class of aromatic compounds.

The third classification feature is the presence of functional groups, groups of atoms, characteristic of this class of compounds and determining its chemical properties. According to the number of functional groups, organic compounds are divided into monofunctional - contain one functional group, polyfunctional - contain several functional groups, such as glycerol, and heterofunctional - several different groups, such as amino acids, in one molecule.

Depending on which carbon atom has a functional group, the compounds are divided into primary, for example, ethyl chloride CH 3 CH 2 C1, secondary - isopropyl chloride (CH3) 2CHC1 and tertiary - butyl chloride (CH 8) 8 CCl.

Alkanes(saturated hydrocarbons, paraffins) - acyclic saturated hydrocarbons of the general formula C n H 2n+2 . In accordance with the general formula, alkanes form homologous series.

The first four representatives have semi-systematic names - methane (CH 4), ethane (C 2 H 6), propane (C 3 H 8), butane (C 4 H 10). The names of the subsequent members of the series are built from the root (Greek numerals) and the suffix - en: pentane (C 5 H 12), hexane (C 6 H 14), heptane (C 7 H 16), etc.

The carbon atoms in alkanes are in sp 3- hybrid state. axes four sp3- orbitals are directed to the vertices of the tetrahedron, the bond angles are 109°28.

Spatial structure of methane:

Energy C-C connection E s - With\u003d 351 kJ / mol, the length of the C-C bond is 0.154 nm.

The C-C bond in alkanes is covalent non-polar. S-N connection - covalent weakly polar.

For alkanes, starting with butane, there are structural isomers(structure isomers) that differ in the order of binding between carbon atoms, with the same qualitative and quantitative composition and molecular weight, but differing in physical properties.

Methods for obtaining alkanes

1. C n H 2n+2 > 400-700°C> С p H 2p+2 + С m H 2m ,

Oil cracking (industrial method). Alkanes are also isolated from natural sources(natural and associated gases, oil, coal).

(hydrogenation of unsaturated compounds)

3. nCO + (2n + 1)H 2 > C n H 2n+2 + nH 2 O (obtained from synthesis gas (CO + H 2))

4. (Wurtz reaction)

5. (Dumas reaction) CH 3 COONa + NaOH > t> CH 4 + Na 2 CO 3

6. (Kolbe reaction)

Chemical properties alkanes

Alkanes are not capable of addition reactions, since all bonds in their molecules are saturated, they are characterized by reactions of radical substitution, thermal decomposition, oxidation, isomerization.

1. (reactivity decreases in the series: F 2 > Cl 2 > Br 2 > (I 2 does not go), R 3 C > R 2 CH > RCH 2 > RCH 3)

2. (Konovalov's reaction)

3. C n H 2n+2 + SO 2 + ?O 2 > h?> C n H 2n+1 SO 3 H - alkyl sulfonic acid

(sulfonic oxidation, reaction conditions: UV irradiation)

4.CH4> 1000°C> C + 2H 2; 2CH4> t>1500 °C> C 2 H 2 + ZN 2 (methane decomposition - pyrolysis)

5. CH 4 + 2H 2 O> Ni, 1300 °C> CO 2 + 4H 2 (methane conversion)

6. 2С n H 2n + 2 + (Зn + 1) O 2 > 2nCO 2 + (2n + 2) Н 2 O (burning of alkanes)

7. 2n- C 4 H 10 + 5O 2 > 4CH 3 COOH + 2H 2 O (oxidation of alkanes in industry; production of acetic acid)

8. n- C 4 H 10 > iso- C 4 H 10 (isomerization, AlCl 3 catalyst)

2. Cycloalkanes

Cycloalkanes(cycloparaffins, naphthenes, cyclanes, polymethylenes) are saturated hydrocarbons with a closed (cyclic) carbon chain. General formula C n H 2n.

The carbon atoms in cycloalkanes, as in alkanes, are in sp 3-hybridized state. homologous series cycloalkanes begins with the simplest cycloalkane - cyclopropane C 3 H 6, which is a flat three-membered carbocycle. According to the rules of international nomenclature in cycloalkanes, the main chain of carbon atoms forming a cycle is considered. The name is built on the name of this closed chain with the addition of the prefix "cyclo" (cyclopropane, cyclobutane, cyclopentane, cyclohexane, etc.).

Structural isomerism of cycloalkanes is associated with different ring sizes (structures 1 and 2), structure and type of substituents (structures 5 and 6), and their mutual arrangement (structures 3 and 4).

Methods for obtaining cycloalkanes

1. Obtaining from dihalogen derivatives of hydrocarbons

2. Preparation from aromatic hydrocarbons

Chemical properties of cycloalkanes

The chemical properties of cycloalkanes depend on the ring size, which determines its stability. Three- and four-membered cycles (small cycles), being saturated, differ sharply from all others saturated hydrocarbons. Cyclopropane, cyclobutane enter into addition reactions. For cycloalkanes (C 5 and above), due to their stability, reactions are characteristic in which the cyclic structure is preserved, i.e., substitution reactions.

1. Action of halogens

2. Action of hydrogen halides

Hydrogen halogens do not react with cycloalkanes containing five or more carbon atoms in the cycle.

4. Dehydrogenation

Alkenes(unsaturated hydrocarbons, ethylene hydrocarbons, olefins) - unsaturated aliphatic hydrocarbons, the molecules of which contain a double bond. The general formula for a number of alkenes C n H 2n.

According to the systematic nomenclature, the names of alkenes are derived from the names of the corresponding alkanes (with the same number of carbon atoms) by replacing the suffix – en on - en: ethane (CH 3 -CH 3) - ethene (CH 2 \u003d CH 2), etc. The main chain is chosen so that it necessarily includes a double bond. The numbering of carbon atoms starts from the end of the chain closest to the double bond.

In an alkene molecule, the unsaturated carbon atoms are in sp 2-hybridization, and the double bond between them is formed by?- and?-bond. sp 2-Hybrid orbitals are directed to each other at an angle of 120 °, and one unhybridized 2p-orbital, located at an angle of 90 ° to the plane of hybrid atomic orbitals.

Spatial structure of ethylene:

C=C bond length 0.134 nm, C=C bond energy E c=c\u003d 611 kJ / mol, energy?-bond E? = 260 kJ/mol.

Types of isomerism: a) chain isomerism; b) double bond position isomerism; V) Z, E (cis, trans) - isomerism, a type of spatial isomerism.

Methods for obtaining alkenes

1. CH 3 -CH 3> Ni, t> CH 2 \u003d CH 2 + H 2 (dehydrogenation of alkanes)

2. C 2 H 5 OH >H,SO 4 , 170 °C> CH 2 \u003d CH 2 + H 2 O (dehydration of alcohols)

3. (dehydrohalogenation of alkyl halides according to the Zaitsev rule)

4. CH 2 Cl-CH 2 Cl + Zn > ZnCl 2 + CH 2 \u003d CH 2 (dehalogenation of dihalogen derivatives)

5. HC?CH + H2> Ni, t> CH 2 \u003d CH 2 (alkyne reduction)

Chemical properties of alkenes

For alkenes, addition reactions are most characteristic; they are easily oxidized and polymerized.

1. CH 2 \u003d CH 2 + Br 2\u003e CH 2 Br-CH 2 Br

(addition of halogens, qualitative reaction)

2. (addition of hydrogen halides according to the Markovnikov rule)

3. CH 2 \u003d CH 2 + H 2> Ni, t> CH 3 -CH 3 (hydrogenation)

4. CH 2 \u003d CH 2 + H 2 O> H+> CH 3 CH 2 OH (hydration)

5. ZCH 2 \u003d CH 2 + 2KMnO 4 + 4H 2 O\u003e ZCH 2 OH-CH 2 OH + 2MnO 2 v + 2KOH (mild oxidation, qualitative reaction)

6. CH 2 \u003d CH-CH 2 -CH 3 + KMnO 4> H+> CO 2 + C 2 H 5 COOH (hard oxidation)

7. CH 2 \u003d CH-CH 2 -CH 3 + O 3\u003e H 2 C \u003d O + CH 3 CH 2 CH \u003d O formaldehyde + propanal> (ozonolysis)

8. C 2 H 4 + 3O 2 > 2CO 2 + 2H 2 O (combustion reaction)

9. (polymerization)

10. CH 3 -CH \u003d CH 2 + HBr\u003e peroxide> CH 3 -CH 2 -CH 2 Br (addition of hydrogen bromide against Markovnikov's rule)

11. (substitution reaction in?-position)

Alkynes(acetylenic hydrocarbons) - unsaturated hydrocarbons that have a triple C?C bond in their composition. The general formula of alkynes with one triple bond is C n H 2n-2. The simplest representative of the CH?CH series of alkynes has the trivial name acetylene. According to the systematic nomenclature, the names of acetylenic hydrocarbons are derived from the names of the corresponding alkanes (with the same number of carbon atoms) by replacing the suffix - en on -in: ethane (CH 3 -CH 3) - ethine (CH? CH), etc. The main chain is chosen so that it necessarily includes a triple bond. The numbering of carbon atoms starts from the end of the chain closest to the triple bond.

The formation of a triple bond involves carbon atoms in sp-hybridized state. Each of them has two sp- hybrid orbitals directed to each other at an angle of 180 °, and two non-hybrid p-orbitals located at an angle of 90° with respect to each other and to sp hybrid orbitals.

Spatial structure of acetylene:

Types of isomerism: 1) isomerism of the position of the triple bond; 2) isomerism of the carbon skeleton; 3) interclass isomerism with alkadienes and cycloalkenes.

Methods for obtaining alkynes

1. CaO + GL > t> CaC 2 + CO;

CaC 2 + 2H 2 O > Ca (OH) 2 + CH? CH (production of acetylene)

2.2CH4> t>1500 °C> HC = CH + ZN 2 (hydrocarbon cracking)

3. CH 3 -CHCl 2 + 2KOH> in alcohol> HC?CH + 2KCl + H 2 O (dehalogenation)

CH 2 Cl-CH 2 Cl + 2KOH> in alcohol> HC?CH + 2KCl + H 2 O

Chemical properties of alkynes

Alkynes are characterized by addition, substitution reactions. Alkynes polymerize, isomerize, enter into condensation reactions.

1. (hydrogenation)

2. HC?CH + Br 2 > CHBr=CHBr;

CHBr \u003d CHBr + Br 2\u003e CHBr 2 -CHBr 2 (addition of halogens, qualitative reaction)

3. CH 3 -C? CH + HBr> CH 3 -CBr \u003d CH 2;

CH 3 -CBr \u003d CH 2 + HBr\u003e CH 3 -CBr 2 -CHg (addition of hydrogen halides according to the Markovnikov rule)

4. (hydration of alines, Kucherov's reaction)

5.(addition of alcohols)

6.(attaching carbon islot)

7.CH?CH + 2Ag2O> NH3> AgC?CAgv + H 2 O (formation of acetylenides, qualitative reaction for terminal triple bond)

8.CH?CH + [O]> KMnO 4> HOOC-COOH > HCOOH + CO 2 (oxidation)

9. CH?CH + CH?CH > CH 2 \u003d CH-C?CH (catalyst - CuCl and NH 4 Cl, dimerization)

10.3HC?CH> C, 600°C> C 6 H 6 (benzene) (cyclooligomerization, Zelinsky reaction)

5. Diene hydrocarbons

Alkadienes(dienes) - unsaturated hydrocarbons, the molecules of which contain two double bonds. The general formula of alkadienes C n H 2n _ 2. The properties of alkadienes largely depend on the mutual arrangement of double bonds in their molecules.

Methods for obtaining dienes

1. (SV. Lebedev's method)

2. (dehydration)

3. (dehydrogenation)

Chemical properties of dienes

For conjugated dienes, addition reactions are characteristic. Conjugated dienes are able to attach not only to double bonds (to C 1 and C 2, C 3 and C 4), but also to the terminal (C 1 and C 4) carbon atoms to form a double bond between C 2 and C 3.

6. Aromatic hydrocarbons

arenas, or aromatic hydrocarbons,- cyclic compounds, the molecules of which contain stable cyclic groups of atoms with a closed system of conjugated bonds, united by the concept of aromaticity, which determines common features in the structure and chemical properties.

All C-C bonds in benzene are equivalent, their length is 0.140 nm. This means that in the benzene molecule there are no purely simple and double bonds between carbon atoms (as in the formula proposed in 1865 by the German chemist F. Kekule), and all of them are aligned (they are localized).

Kekule formula

Benzene homologues are compounds formed by replacing one or more hydrogen atoms in a benzene molecule with hydrocarbon radicals (R): C 6 H 5 -R, R-C 6 H 4 -R. The general formula for the homologous series of benzene C n H 2n _ 6 (n> 6). Trivial names (toluene, xylene, cumene, etc.) are widely used for the names of aromatic hydrocarbons. Systematic names are built from the name of the hydrocarbon radical (prefix) and the word "benzene" (root): C 6 H 5 -CH 3 (methylbenzene), C 6 H 5 -C 2 H 5 (ethylbenzene). If there are two or more radicals, their position is indicated by the numbers of the carbon atoms in the ring to which they are attached. For disubstituted benzenes R-C 6 H 4 -R, another method of constructing names is also used, in which the position of the substituents is indicated before the trivial name of the compound with prefixes: ortho-(o-) - substituents of neighboring carbon atoms of the ring (1,2-); meta-(m-) - substituents through one carbon atom (1,3-); pair-(P-) - substituents on opposite sides rings (1,4-).

Types of isomerism (structural): 1) positions of substituents for di-, tri- and tetra-substituted benzenes (for example, o-, m- And P-xylenes); 2) a carbon skeleton in a side chain containing at least 3 carbon atoms; 3) substituents (R), starting with R=C 2 H 5 .

Methods for obtaining aromatic hydrocarbons

1. C 6 H 12 > Pt, 300 °C> С 6 Н 6 + ЗН 2 (dehydrogenation of cycloalkanes)

2. n- C 6 H 14 > Cr2O3, 300°C> C 6 H 6 + 4H 2 (dehydrocyclization of alkanes)

3. ZS 2 H 2 > C, 600 °C> C 6 H 6 (cyclotrimerization of acetylene, Zelinsky reaction)

Chemical properties of aromatic hydrocarbons

By chemical properties, arenas differ from saturated and unsaturated hydrocarbons. For arenes, the most characteristic reactions proceed with the preservation of the aromatic system, namely, the substitution reactions of hydrogen atoms associated with the cycle. Other reactions (addition, oxidation), in which delocalized C-C bonds of the benzene ring are involved and its aromaticity is disturbed, go with difficulty.

1. C 6 H 6 + Cl 2> AlCl 3> C 6 H 5 Cl + HCl (halogenation)

2. C 6 H 6 + HNO 3 > H2SO4> C 6 H 5 -NO 2 + H 2 O (nitration)

3. C 6 H 6 > H2SO4> C 6 H 5 -SO 3 H + H 2 O (sulfonation)

4. C 6 H 6 + RCl> AlCl 3> C 6 H 5 -R + HCl (alkylation)

5. (acylation)

6. C 6 H 6 + ZN 2> t, Ni> C 6 H 12 cyclohexane (hydrogen addition)

7. (1,2,3,4,5,6-hexachlorocyclohexane, addition of chlorine)

8. C 6 H 5 -CH 3 + [O]> C 6 H 5 -COOH boiling with a solution of KMnO 4 (oxidation of alkylbenzenes)

7. Halogenated hydrocarbons

halocarbons called derivatives of hydrocarbons in which one or more hydrogen atoms are replaced by halogen atoms.

Methods for producing halocarbons

1. CH 2 \u003d CH 2 + HBr\u003e CH 3 -CH 2 Br (hydrohalogenation of unsaturated hydrocarbons)

CH?CH + HCl > CH 2 \u003d CHCl

2. CH 3 CH 2 OH + РCl 5 > CH 3 CH 2 Cl + POCl 3 + HCl (preparation from alcohols)

CH 3 CH 2 OH + HCl > CH 3 CH 2 Cl + H 2 O (in the presence of ZnCl 2, t°C)

3. a) CH 4 + Cl 2 >hv> CH 3 Cl + HCl (halogenation of hydrocarbons)

Chemical properties of halocarbons

Highest value for compounds of this class, they have substitution and elimination reactions.

1. CH 3 CH 2 Br + NaOH (aqueous solution) > CH 3 CH 2 OH + NaBr (formation of alcohols)

2. CH 3 CH 2 Br + NaCN > CH 3 CH 2 CN + NaBr (formation of nitriles)

3. CH 3 CH 2 Br + NH 3 > + Br - HBr- CH 3 CH 2 NH 2 (formation of amines)

4. CH 3 CH 2 Br + NaNO 2 > CH 3 CH 2 NO 2 + NaBr (formation of nitro compounds)

5. CH 3 Br + 2Na + CH 3 Br > CH 3 -CH 3 + 2NaBr (Wurtz reaction)

6. CH 3 Br + Mg > CH 3 MgBr (formation of organomagnesium compounds, Grignard reagent)

7. (dehydrohalogenation)

alcohols called derivatives of hydrocarbons, the molecules of which contain one or more hydroxyl groups (-OH) associated with saturated carbon atoms. The -OH group (hydroxyl, hydroxy group) is a functional group in the alcohol molecule. Systematic names are given by the name of the hydrocarbon with the addition of the suffix - ol and a number indicating the position of the hydroxyl group. The numbering is carried out from the end of the chain closest to the OH group.

According to the number of hydroxyl groups, alcohols are divided into monohydric (one -OH group), polyhydric (two or more -OH groups). Monohydric alcohols: methanol CH 3 OH, ethanol C 2 H 5 OH; dihydric alcohol: ethylene glycol (ethanediol-1,2) HO-CH 2 -CH 2 -OH; trihydric alcohol: glycerol (propanetriol-1,2,3) HO-CH 2 -CH(OH)-CH 2 -OH. Depending on which carbon atom (primary, secondary or tertiary) the hydroxy group is associated with, primary alcohols R-CH 2 -OH, secondary R 2 CH-OH, tertiary R 3 C-OH are distinguished.

According to the structure of the radicals associated with the oxygen atom, alcohols are divided into saturated, or alkanols (CH 3 CH 2 -OH), unsaturated, or alkenols (CH 2 \u003d CH-CH 2 -OH), aromatic (C 6 H 5 CH 2 - OH).

Types of isomerism (structural isomerism): 1) isomerism of the position of the OH group (starting from C 3); 2) carbon skeleton (starting from C 4); 3) interclass isomerism with ethers (for example, ethyl alcohol CH 3 CH 2 OH and dimethyl ether CH 3 -O-CH 3). The consequence of the polarity of the O-H bond and the presence of lone pairs of electrons on the oxygen atom is the ability of alcohols to form hydrogen bonds.

Methods for obtaining alcohols

1. CH 2 \u003d CH 2 + H 2 O / H +\u003e CH 3 -CH 2 OH (alkene hydration)

2. CH 3 -CHO + H 2> t, Ni> C 2 H 5 OH (reduction of aldehydes and ketones)

3. C 2 H 5 Br + NaOH (aq.) > C 2 H 5 OH + NaBr (hydrolysis of halogen derivatives)

ClCH 2 -CH 2 Cl + 2NaOH (aq.) > HOCH 2 -CH 2 OH + 2NaCl

4. CO + 2H 2> ZnO, CuO, 250 °C, 7 MPa> CH 3 OH (methanol production, industry)

5. C 6 H 12 O 6 > yeast> 2C 2 H 5 OH + 2CO 2 (monose fermentation)

6. 3CH 2 \u003d CH 2 + 2KMnO 4 + 4H 2 O\u003e 3CH 2 OH-CH 2 OH - ethylene glycol+ 2KOH + 2MnO 2 (oxidation under mild conditions)

7. a) CH 2 \u003d CH-CH 3 + O 2\u003e CH 2 \u003d CH-CHO + H 2 O

b) CH 2 \u003d CH-CHO + H 2\u003e CH 2 \u003d CH-CH 2 OH

c) CH 2 \u003d CH-CH 2 OH + H 2 O 2\u003e HOCH 2 -CH (OH) -CH 2 OH (obtaining glycerol)

Chemical properties of alcohols

The chemical properties of alcohols are associated with the presence of the -OH group in their molecule. Alcohols are characterized by two types of reactions: cleavage C-O connections and O-N connections.

1. 2C 2 H 5 OH + 2Na > H 2 + 2C 2 H 5 ONa (formation of metal alcoholates Na, K, Mg, Al)

2. a) C 2 H 5 OH + NaOH? (does not work in aqueous solution)

b) CH 2 OH-CH 2 OH + 2NaOH> NaOCH 2 -CH 2 ONa + 2H 2 O

c) (qualitative reaction to polyhydric alcohols - the formation of a bright blue solution with copper hydroxide)

3. a) (formation of esters)

b) C 2 H 5 OH + H 2 SO 4 > C 2 H 5 -O-SO 3 H + H 2 O (in the cold)

4. a) C 2 H 5 OH + HBr> C 2 H 5 Br + H 2 O

b) C 2 H 5 OH + РCl 5 > C 2 H 5 Cl + POCl 3 + HCl

c) C 2 H 5 OH + SOCl 2 > C 2 H 5 Cl + SO 2 + HCl (replacement of the hydroxyl group by halogen)

5. C 2 H 5 OH + HOC 2 H 5 > H2SO4,<140 °C > C 2 H 5 -O-C 2 H 5 + H 2 O (intermolecular hydration)

6. C 2 H 5 OH> H2SO4, 170°C> CH 2 \u003d CH 2 + H 2 O (intramolecular hydration)

7. a) (dehydrogenation, oxidation of primary alcohols)

Phenols arene derivatives are called, in which one or more hydrogen atoms of the aromatic ring are replaced by hydroxyl groups. According to the number of hydroxyl groups in the aromatic ring, mono- and polyatomic (two- and three-atomic) phenols are distinguished. Trivial names are used for most phenols. Structural isomerism of phenols is associated with different positions of hydroxyl groups.

Methods for obtaining phenols

1. C 6 H 5 Cl + NaOH(p, 340°C) > C 6 H 5 OH + NaCl (alkaline hydrolysis of halocarbons)

2. (cumene method of obtaining)

3. C 6 H 5 SO 3 Na + NaOH (300–350°C) > C 6 H 5 OH + Na 2 SO 3 (alkaline melting of salts of aromatic sulfonic acids)

Chemical properties of phenols

Phenols in most bond reactions O-N more active alcohols, since this bond is more polar due to the shift of the electron density from the oxygen atom towards the benzene ring (participation of the unshared electron pair of the oxygen atom in the n-conjugation system). The acidity of phenols is much higher than that of alcohols.

For phenols, C-O bond cleavage reactions are not typical. Mutual influence atoms in the phenol molecule manifests itself not only in the behavior of the hydroxy group, but also in the greater reactivity of the benzene ring.

The hydroxyl group increases the electron density in the benzene ring, especially in ortho- And pair- positions (+ M effect of the OH group). For the detection of phenols, a qualitative reaction with iron(III) chloride is used. Monatomic phenols give a stable blue-violet color, which is associated with the formation complex compounds gland.

1. 2C 6 H 5 OH + 2Na > 2C 6 H 5 ONa + H 2 (same as ethanol)

2. C 6 H 5 OH + NaOH > C 6 H 5 ONa + H 2 O (unlike ethanol)

C 6 H 5 ONa + H 2 O + CO 2 > C 6 H 5 OH + NaHCO 3 (phenol is a weaker acid than carbonic)

Phenols do not form esters in reactions with acids. For this, more reactive acid derivatives (anhydrides, acid chlorides) are used.

4. C 6 H 5 OH + CH 3 CH 2 OH> NaOH> C 6 H 5 OCH 2 CH 3 + NaBr (O-alkylation)

(interaction with bromine water, qualitative reaction)

6. (Nitration dilute HNO 3, nitration with conc. HNO 3 produces 2,4,6-trinitrophenol)

7. n C6H5OH+ n CH2O> n H 2 O + (-C 6 H 3 OH-CH 2 -) n(polycondensation, obtaining phenol-formaldehyde resins)

10. Aldehydes and ketones

Aldehydes are compounds in which the carbonyl group

connected to a hydrocarbon radical and a hydrogen atom, and ketones- carbonyl compounds with two hydrocarbon radicals.

The systematic names of aldehydes are built on the name of the corresponding hydrocarbon with the addition of a suffix –al. The chain numbering starts from the carbonyl carbon atom. Trivial names are derived from the trivial names of those acids into which aldehydes are converted during oxidation: H 2 C \u003d O - methanal (formaldehyde, formaldehyde); CH 3 CH=O - ethanal (acetic aldehyde). The systematic names of ketones of a simple structure are derived from the names of the radicals with the addition of the word "ketone". In a more general case, the name of a ketone is constructed from the name of the corresponding hydrocarbon and the suffix -He; chain numbering starts from the end of the chain closest to the carbonyl group. Examples: CH 3 -CO-CH 3 - dimethyl ketone (propanone, acetone). Aldehydes and ketones are characterized by structural isomerism. Isomerism of aldehydes: a) isomerism of the carbon skeleton, starting from C 4; b) interclass isomerism. Isomerism of ketones: a) carbon skeleton (with C 5); b) positions of the carbonyl group (with C 5); c) interclass isomerism.

The carbon and oxygen atoms in the carbonyl group are in the state sp2- hybridization. The C=O bond is highly polar. The electrons of the C=O multiple bond are shifted to the electronegative oxygen atom, which leads to the appearance of a partial negative charge on it, and the carbonyl carbon atom acquires a partial positive charge.

Methods for obtaining aldehydes and ketones

1. a) (dehydrogenation, oxidation of primary alcohols)

b) (dehydrogenation, oxidation of secondary alcohols)

2. a) CH 3 CH 2 CHCl 2 + 2NaOH> in water> CH 3 CH 2 CHO + 2NaCl + H 2 O (hydrolysis of dihalogen derivatives)

b) CH 3 СCl 2 CH 3 + 2NaOH> in water> CH 3 COCH 3 + 2NaCl + H 2 O

3. (hydration of alkynes, Kucherov reaction)

4. (oxidation of ethylene to ethanal)

(methane oxidation to formaldehyde)

CH 4 + O 2 > 400-600°C NO> H 2 C \u003d O + H 2 O

Chemical properties of aldehydes and ketones

For carbonyl compounds, reactions of various types are characteristic: a) addition to the carbonyl group; b) reduction and oxidation; c) condensation; e) polymerization.

1. (addition of hydrocyanic acid, formation of hydroxynitriles)

2. (addition of sodium hydrosulphite)

3. (recovery)

4. (formation of hemiacetals and acetals)

5. (interaction with hydroxolamine, formation of acetaldehyde oxime)

6. (formation of dihalogen derivatives)

7. (?-halogenation in the presence of OH?)

8. (albdol condensation)

9. R-CH \u003d O + Ag 2 O> NH3> R-COOH + 2Agv (oxidation, silver mirror reaction)

R-CH \u003d O + 2Cu (OH) 2\u003e R-COOH + Cu 2 Ov, + 2H 2 O (red precipitate, oxidation)

10. (ketone oxidation, severe conditions)

11. n CH 2 \u003d O\u003e (-CH2-O-) n paraforms n= 8-12 (polymerization)

11. Carboxylic acids and their derivatives

carboxylic acids called organic compounds containing one or more carboxyl groups -COOH associated with a hydrocarbon radical. According to the number of carboxyl groups, acids are divided into: monobasic (monocarboxylic) CH 3 COOH (acetic), polybasic (dicarboxylic, tricarboxylic, etc.). According to the nature of the hydrocarbon radical, acids are distinguished: limiting (for example, CH 3 CH 2 CH 2 COOH); unsaturated (CH 2 \u003d CH (-COOH); aromatic (C 6 H 5 COOH).

The systematic names of acids are given by the name of the corresponding hydrocarbon with the addition of the suffix –new and the words "acid": HCOOH - methane (formic) acid, CH 3 COOH - ethanoic (acetic) acid. For carboxylic acids, the characteristic structural isomerism is: a) skeletal isomerism in the hydrocarbon radical (starting from C 4); b) interclass isomerism, starting from C 2 . Possible cis-trans isomerism in the case of unsaturated carboxylic acids. electron density? - bonds in the carbonyl group are shifted towards the oxygen atom. As a result, carbonyl carbon has a lack of electron density, and it attracts lone pairs of the oxygen atom of the hydroxyl group, as a result of which the electron density of the O-H bond shifts towards the oxygen atom, hydrogen becomes mobile and acquires the ability to split off in the form of a proton.

In an aqueous solution, carboxylic acids dissociate into ions:

R-COOH - R-COO? + H +

Solubility in water and high boiling points of acids are due to the formation of intermolecular hydrogen bonds.

Methods for obtaining carboxylic acids

1. CH 3 -CCl 3 + 3NaOH > CH 3 -COOH + 3NaCl + H 2 O (hydrolysis of trihalogen derivatives)

2. R-CHO + [O] > R-COOH (oxidation of aldehydes and ketones)

3. CH 3 -CH \u003d CH 2 + CO + H 2 O / H + > Ni, p, t> CH 3 -CH 2 -CH 2 -COOH (oxosynthesis)

4. CH 3 C?N + 2H 2 O / H + > CH 3 COOH + NH 4 (hydrolysis of nitriles)

5. CO + NaOH > HCOONa; 2HCOONa + H 2 SO 4 > 2HCOOH + Na 2 SO 4 (obtaining HCOOH)

Chemical properties of carboxylic acids and their derivatives

Carboxylic acids exhibit high reactivity and react with various substances, forming a variety of compounds, among which functional derivatives are of great importance: esters, amides, nitriles, salts, anhydrides, halogen anhydrides.

1. a) 2CH 3 COOH + Fe > (CH 3 COO) 2 Fe + H 2 (formation of salts)

b) 2CH 3 COOH + MgO > (CH 3 COO) 2 Mg + H 2 O

c) CH 3 COOH + KOH > CH 3 COOK + H 2 O

d) CH 3 COOH + NaHCO 3 > CH 3 COONa + CO 2 + H 2 O

CH 3 COONa + H 2 O - CH 3 COOH + NaOH (salts of carboxylic acids are hydrolyzed)

2. (formation of nested esters)

(saponification of nested ether)

3. (obtaining acid chlorides)

4. (water decomposition)

5. CH 3 -COOH + Cl 2> hv> Cl-CH 2 -COOH + HCl (halogenation in?-position)

6. HO-CH \u003d O + Ag 2 O> NH3> 2Ag + H 2 CO 3 (H 2 O + CO 2) (HCOOH features)

HCOOH > t> CO + H 2 O

Fats- esters of glycerol and higher monohydric carboxylic acids. Common name such compounds are triglycerides. The composition of natural triglycerides includes residues of saturated acids (palmitic C 15 H 31 COOH, stearic C 17 H 35 COOH) and unsaturated acids (oleic C 17 H 33 COOH, linoleic C 17 H 31 COOH). Fats consist mainly of triglycerides of saturated acids. Vegetable fats - oils (sunflower, soybean) - liquids. The composition of triglycerides of oils includes residues of unsaturated acids.

Fats as esters are characteristic reversible reaction hydrolysis catalyzed by mineral acids. With the participation of alkalis, the hydrolysis of fats occurs irreversibly. The products in this case are soaps - salts of higher carboxylic acids and alkali metals. Sodium salts are solid soaps, potassium salts are liquid. The reaction of alkaline hydrolysis of fats is also called saponification.

Amines- organic derivatives of ammonia, in the molecule of which one, two or three hydrogen atoms are replaced by hydrocarbon radicals. Depending on the number of hydrocarbon radicals, primary RNH 2 , secondary R 2 NH, tertiary R 3 N amines are distinguished. According to the nature of the hydrocarbon radical, amines are divided into aliphatic (fatty), aromatic and mixed (or fatty-aromatic). The names of amines in most cases are formed from the names of hydrocarbon radicals and the suffix -amine. For example, CH 3 NH 2 is methylamine; CH 3 -CH 2 -NH 2 - ethylamine. If the amine contains various radicals, then they are listed in alphabetical order: CH 3 -CH 2 -NH-CH 3 - methylethylamine.

The isomerism of amines is determined by the number and structure of radicals, as well as the position of the amino group. N-H connection is polar, so primary and secondary amines form intermolecular hydrogen bonds. Tertiary amines do not form associated hydrogen bonds. Amines are capable of forming hydrogen bonds with water. Therefore, lower amines are highly soluble in water. With an increase in the number and size of hydrocarbon radicals, the solubility of amines in water decreases.

Methods for obtaining amines

1. R-NO 2 + 6 [H] > R-NH 2 + 2H 2 O (reduction of nitro compounds)

2. NH 3 + CH 3 I > I? > NH3> CH 3 NH 2 + NH 4 I (ammonia alkylation)

3. a) C 6 H 5 -NO 2 + 3 (NH 4) 2 S> C 6 H 5 -NH 2 + 3S + 6NH 3 + 2H 2 O (Zinin reaction)

b) C 6 H 5 -NO 2 + 3Fe + 6HCl> C 6 H 5 -NH 2 + 3FeCl 2 + 2H 2 O (reduction of nitro compounds)

c) C 6 H 5 -NO 2 + ZN 2> catalyst, t> C 6 H 5 -NH 2 + 2H 2 O

4. R-C?N + 4[H]> RCH 2 NH 2 (reduction of nitriles)

5. ROH + NH 3 > Al 2 O 3 ,350 °C> RNH 2 + 2H 2 O (obtaining lower alkylamines C 2 -C 4)

Chemical properties of amines

Amines have a structure similar to ammonia and exhibit similar properties. In both ammonia and amines, the nitrogen atom has a lone pair of electrons. Amines are characterized by pronounced basic properties. Aqueous solutions aliphatic amines exhibit an alkaline reaction. Aliphatic amines are stronger bases than ammonia. Aromatic amines are weaker bases than ammonia, since the unshared electron pair of the nitrogen atom is shifted towards the benzene ring, conjugating with its ?-electrons.

The basicity of amines is influenced by various factors: the electronic effects of hydrocarbon radicals, the spatial shielding of the nitrogen atom by radicals, and the ability of the resulting ions to stabilize due to solvation in a solvent medium. As a result of the donor effect of alkyl groups, the basicity of aliphatic amines in the gas phase (without solvent) increases in the series: primary< вторичные < третичные. Основность ароматических аминов зависит также от характера заместителей в бензольном кольце. Электроноакцепторные заместители (-F, -Cl, -NO 2 и т. п.) уменьшают основные свойства ариламина по сравнению с анилином, а электронодонорные (алкил R-, -OCH 3 , -N(CH 3) 2 и др.), напротив, увеличивают.

1. CH 3 -NH 2 + H 2 O> OH (interaction with water)

2. (CH 3) 2 NH + HCl > [(CH 3) 2 NH 2] Cl dimethylammonium chloride (reaction with acids)

[(CH 3) 2 NH 2] Cl + NaOH > (CH 3) 2 NH + NaCl + H 2 O (reaction of amine salts with alkalis)

(acylation, does not work with tertiary amines)

4. R-NH 2 + CH 3 I> I? > NH3> CH 3 NHR + NH 4 I (alkylation)

5. Interaction with nitrous acid: the structure of the reaction products with nitrous acid depends on the nature of the amine. Therefore, this reaction is used to distinguish between primary, secondary and tertiary amines.

a) R-NH 2 + HNO 2 > R-OH + N 2 + H 2 O (primary fatty amines)

b) C 6 H 5 -NH 2 + NaNO 2 + HCl> [C 6 H 5 -N? N] + Cl? – diazonium salt (primary aromatic amines)

c) R 2 NH + H-O-N \u003d O\u003e R 2 N-N \u003d O (N-nitrosamine) + H 2 O (secondary fatty and aromatic amines)

d) R 3 N + H-O-N \u003d O\u003e no reaction at low temperature (tertiary fatty amines)

(tertiary aromatic amines)

properties of aniline. Aniline is characterized by reactions both at the amino group and at the benzene ring. The benzene ring weakens the basic properties of the amino group compared to aliphatic amines and ammonia, but under the influence of the amino group, the benzene ring becomes more active in substitution reactions compared to benzene.

C 6 H 5 -NH 2 + HCl > Cl \u003d C 6 H 5 NH 2 HCl

C 6 H 5 NH 2 HCl + NaOH > C 6 H 5 NH 2 + NaCl + H 2 O

C 6 H 5 NH 2 + CH3I> t> +I?

14. Amino acids

Amino acids called hetero-functional compounds, the molecules of which contain both an amino group and a carboxyl group. Depending on the mutual arrangement of the amino and carboxyl groups, amino acids are divided into amino-, indicating the number of the carbon atom to which it is bonded, followed by the name of the corresponding acid.

2-aminopropanoic acid (?-aminopropanoic, ?-alanine) 3-aminopropanoic acid (?-aminopropanoic, ?-alanine) 6-aminohexanoic acid (?-aminocaproic)

By the nature of the hydrocarbon radical, aliphatic (fatty) and aromatic amino acids are distinguished. The isomerism of amino acids depends on the structure of the carbon skeleton, the position of the amino group in relation to the carboxyl group. Amino acids are also characterized by optical isomerism.

Methods for obtaining amino acids

1. (ammonolysis of halogen acids)

2. CH 2 \u003d CH-COOH + NH 3 > H 2 N-CH 2 -CH 2 -COOH (ammonia addition to ?, ?-unsaturated acids)

(action of HCN and NH 3 on aldehydes or ketones)

4. Hydrolysis of proteins under the influence of enzymes, acids or alkalis.

5. Microbiological synthesis.

Chemical properties of amino acids

Amino acids exhibit the properties of bases due to the amino group and the properties of acids due to carboxyl group, i.e., they are amphoteric compounds. In the crystalline state and in an environment close to neutral, amino acids exist in the form of an internal salt - a dipolar ion, also called the zwitterion H 3 N + -CH 2 -COO?.

1. H 2 N-CH 2 -COOH + HCl> Cl? (formation of salts at the amino group)

2. H 2 N-CH 2 -COOH + NaOH> H 2 N-CH 2 -COO? Na + + H 2 O (formation of salts)

(ester formation)

(acylation)

5. + NH 3 -CH 2 -COO? + 3CH 3 I > -HI> (CH 3) 3 N + -CH 2 -COO? – aminoacetic acid betaine

(alkylation)

(interaction with nitrous acid)

7. n H 2 N-(CH 2) 5 -COOH> (-HN-(CH 2) 5 -CO-) n+ n H 2 O (obtaining capron)

15. Carbohydrates. Monosaccharides. Oligosaccharides. Polysaccharides

Carbohydrates(sugar) - organic compounds having a similar structure and properties, the composition of most of which is reflected by the formula С x (Н 2 O) y, where x, y? 3.

Classification:

Monosaccharides are not hydrolyzed to form simpler carbohydrates. Oligo- and polysaccharides are cleaved by acid hydrolysis to monosaccharides. Well-known representatives: glucose (grape sugar) C 6 H 12 O 6, sucrose (cane, beet sugar) C 12 H 22 O 11, starch and cellulose [C 6 H 10 O 5] n.

How to get

1. mCO 2 + nH 2 O > hv, chlorophyll> C m (H 2 O) n (carbohydrates) + mO 2 (obtained by photosynthesis)

carbohydrates: C 6 H 12 O 6 + 6O 2 > 6CO 2 + 6H 2 O + 2920 kJ

(metabolism: glucose is oxidized with the release of a large amount of energy in a living organism during metabolism)

2. 6nCO 2 + 5nH 2 O > hv, chlorophyll> (C 6 H 10 O 5) n + 6nO 2 (obtaining starch or cellulose)

Chemical properties

Monosaccharides. All monoses in the crystalline state have a cyclic structure (?- or?-). When dissolved in water, the cyclic hemiacetal is destroyed, turning into a linear (oxo-) form.

The chemical properties of monosaccharides are due to the presence of three types of functional groups in the molecule (carbonyl, alcohol hydroxyls, and glycosidic (hemiacetal) hydroxyl).

1. C 5 H 11 O 5 -CHO (glucose) + Ag 2 O > NH 3 > CH 2 OH- (CHOH) 4 -COOH (gluconic acid) + 2Ag (oxidation)

2. C 5 H 11 O 5 -CHO (glucose) + [H]> CH 2 OH-(CHOH) 4 -CH 2 OH (sorbitol) (reduction)

(monoalkylation)

(polyalkylation)

5. The most important property of monosaccharides is their enzymatic fermentation, i.e., the breakdown of molecules into fragments under the action of various enzymes. Fermentation is mainly carried out by hexoses in the presence of enzymes secreted by yeasts, bacteria or molds. Depending on the nature of the active enzyme, reactions of the following types are distinguished:

a) C 6 H 12 O 6 > 2C 2 H 5 OH + 2CO 2 (alcoholic fermentation);

b) C 6 H 12 O 6 > 2CH 3 -CH (OH) -COOH (lactic acid fermentation);

c) C 6 H 12 O 6 > C 3 H 7 COOH + 2CO 2 + 2H 2 O (butyric fermentation);

d) C 6 H 12 O 6 + O 2 > HOOC-CH 2 -C (OH) (COOH) -CH 2 -COOH + 2H 2 O (citric acid fermentation);

e) 2C 6 H 12 O 6 > C 4 H 9 OH + CH 3 -CO-CH 3 + 5CO 2 + 4H 2 (acetone-butanol fermentation).

Disaccharides. Disaccharides are carbohydrates whose molecules consist of two monosaccharide residues connected to each other by the interaction of hydroxyl groups (two hemiacetal or one hemiacetal and one alcohol). The absence or presence of glycosidic (hemiacetal) hydroxyl affects the properties of disaccharides. Bioses are divided into two groups: regenerating And non-restoring. Reducing bioses are able to exhibit the properties of reducing agents and, when interacting with ammonia solution silver is oxidized to the corresponding acids, contain glycosidic hydroxyl in their structure, the bond between monoses is glycoside-glycose. Education scheme regenerating bios on the example of maltose:

Disaccharides are characterized by a hydrolysis reaction, as a result of which two molecules of monosaccharides are formed:

An example of the most common disaccharides in nature is sucrose (beet or cane sugar). The sucrose molecule consists of β-D-glucopyranose and β-D-fructofuranose residues connected to each other through the interaction of hemiacetal (glycosidic) hydroxyls. Bioses of this type do not show reducing properties, since they do not contain glycosidic hydroxyl in their structure, the relationship between monoses is glycoside-glycosidic. These disaccharides are called non-restoring, i.e. not able to oxidize.

The scheme of formation of sucrose:

Sucrose inversion. Acid hydrolysis of (+) sucrose or the action of invertase produces equal amounts of D (+) glucose and D (-) fructose. Hydrolysis is accompanied by a change in the sign of the specific rotation angle [?] from positive to negative; therefore, the process is called inversion, and the mixture of D(+)glucose and D(-)fructose is called invert sugar.

Polysaccharides (polioses). Polysaccharides are natural high-molecular carbohydrates, the macromolecules of which consist of monosaccharide residues. Main representatives: starch And cellulose, which are built from residues of one monosaccharide - D-glucose. Starch and cellulose have the same molecular formula: (C 6 H 10 O 5) n, but different properties. This is due to the peculiarities of their spatial structure. Starch is made up of ?-D-glucose residues, while cellulose is made up of ?-D-glucose. Starch- a reserve polysaccharide of plants, accumulates in the form of grains in the cells of seeds, bulbs, leaves, stems, is a white amorphous substance insoluble in cold water. Starch - mixture amylose And amylopectin, which are built from residues? -D-glucopyranose.

amylose– linear polysaccharide, the relationship between the residues of D-glucose 1?-4. The chain shape is helical, one turn of the helix contains 6 D-glucose residues. The content of amylose in starch is 15–25%.

amylose
amylopectin

Amylopectin– branched polysaccharide, bonds between D-glucose residues – 1?-4 and 1?-6. The content of amylopectin in starch is 75–85%.

1. Formation of ethers and esters (similar to bioses).

2. Qualitative reaction - staining with the addition of iodine: for amylose - in blue, for amylopectin - in red.

3. Acid hydrolysis of starch: starch > dextrins > maltose > α-D-glucose.

Cellulose. Structural polysaccharide of plants, built from residues of β-D-glucopyranose, the nature of the compound is 1β-4. The content of cellulose, for example, in cotton is 90-99%, in hardwoods - 40-50%. This biopolymer has high mechanical strength and acts as a supporting material for plants, forming the walls of plant cells.

Characterization of chemical properties

1. Acid hydrolysis (saccharification): cellulose > cellobiose > α-D-glucose.

2. Formation of esters

Acetate fibers are made from solutions of cellulose acetate in acetone.

Nitrocellulose is explosive and forms the basis of smokeless powder. Pyroxylin - a mixture of di- and trinitrates of cellulose - is used for the manufacture of celluloid, collodion, photographic films, varnishes.

In the past, scientists divided all substances in nature into conditionally inanimate and living ones, including the animal and plant kingdoms among the latter. Substances of the first group are called mineral. And those that entered the second, began to be called organic substances.

What is meant by this? The class of organic substances is the most extensive among all chemical compounds known to modern scientists. The question of which substances are organic can be answered as follows - these are chemical compounds that include carbon.

Please note that not all carbon-containing compounds are organic. For example, corbides and carbonates, carbonic acid and cyanides, carbon oxides are not among them.

Why are there so many organic substances?

The answer to this question lies in the properties of carbon. This element is curious in that it is able to form chains from its atoms. And at the same time, the carbon bond is very stable.

In addition, in organic compounds, it exhibits a high valence (IV), i.e. the ability to form chemical bonds with other substances. And not only single, but also double and even triple (otherwise - multiples). As the bond multiplicity increases, the chain of atoms becomes shorter, and the bond stability increases.

And carbon is endowed with the ability to form linear, flat and three-dimensional structures.

That is why organic substances in nature are so diverse. You can easily check it yourself: stand in front of a mirror and carefully look at your reflection. Each of us is a walking textbook on organic chemistry. Think about it: at least 30% of the mass of each of your cells is organic compounds. The proteins that built your body. Carbohydrates, which serve as "fuel" and a source of energy. Fats that store energy reserves. Hormones that control organ function and even your behavior. Enzymes that start chemical reactions within you. And even the "source code," the strands of DNA, are all carbon-based organic compounds.

Composition of organic substances

As we said at the very beginning, the main building material for organic matter is carbon. And practically any elements, combining with carbon, can form organic compounds.

In nature, most often in the composition of organic substances are hydrogen, oxygen, nitrogen, sulfur and phosphorus.

The structure of organic substances

The diversity of organic substances on the planet and the diversity of their structure can be explained characteristic features carbon atoms.

You remember that carbon atoms are able to form very strong bonds with each other, connecting in chains. The result is stable molecules. The way in which carbon atoms chain together (arrange in a zigzag pattern) is one of the key features her buildings. Carbon can combine both into open chains and into closed (cyclic) chains.

It is also important that the structure chemical substances directly affects their chemical properties. A significant role is also played by how atoms and groups of atoms in a molecule affect each other.

Due to the peculiarities of the structure, the number of carbon compounds of the same type goes to tens and hundreds. For an example, consider hydrogen compounds carbon: methane, ethane, propane, butane, etc.

For example, methane - CH 4. This combination of hydrogen and carbon normal conditions resides in a gaseous state of aggregation. When oxygen appears in the composition, a liquid is formed - methyl alcohol CH 3 OH.

Not only substances with different qualitative composition (as in the example above) exhibit different properties, but substances of the same qualitative composition are also capable of this. An example is the different ability of methane CH 4 and ethylene C 2 H 4 to react with bromine and chlorine. Methane is capable of such reactions only when heated or under ultraviolet light. And ethylene reacts even without lighting and heating.

Consider this option: the qualitative composition of chemical compounds is the same, the quantitative is different. Then the chemical properties of the compounds are different. As in the case of acetylene C 2 H 2 and benzene C 6 H 6.

Not the last role in this variety is played by such properties of organic substances, "tied" to their structure, as isomerism and homology.

Imagine that you have two seemingly identical substances - the same composition and the same molecular formula to describe them. But the structure of these substances is fundamentally different, from which follows the difference in chemical and physical properties. For example, the molecular formula C 4 H 10 can be written for two different substances: butane and isobutane.

We are talking about isomers- compounds that have the same composition and molecular weight. But the atoms in their molecules are located in a different order (branched and unbranched structure).

Concerning homology- this is a characteristic of such a carbon chain in which each next member can be obtained by adding one CH 2 group to the previous one. Each homologous series can be expressed by one general formula. And knowing the formula, it is easy to determine the composition of any of the members of the series. For example, methane homologues are described by the formula C n H 2n+2 .

As the “homologous difference” CH 2 is added, the bond between the atoms of the substance is strengthened. Let's take the homologous series of methane: its first four members are gases (methane, ethane, propane, butane), the next six are liquids (pentane, hexane, heptane, octane, nonane, decane), and then substances in the solid state of aggregation follow (pentadecane, eicosan, etc.). And the stronger the bond between carbon atoms, the higher molecular weight, boiling and melting points of substances.

What classes of organic substances exist?

Organic substances of biological origin include:

• proteins;
• carbohydrates;
• nucleic acids;
• lipids.

The first three points can also be called biological polymers.

A more detailed classification of organic chemicals covers substances not only of biological origin.

The hydrocarbons are:

• acyclic compounds:
  • saturated hydrocarbons (alkanes);
  • unsaturated hydrocarbons:
    • alkenes;
    • alkynes;
    • alkadienes.
• cyclic compounds:
  • carbocyclic compounds:
    • alicyclic;
    • aromatic.
  • heterocyclic compounds.

There are also other classes of organic compounds in which carbon combines with substances other than hydrogen:

• alcohols and phenols;
• aldehydes and ketones;
• carboxylic acids;
• esters;
• lipids;
• carbohydrates:
  • monosaccharides;
  • oligosaccharides;
  • polysaccharides.
  • mucopolysaccharides.
• amines;
• amino acids;
• proteins;
• nucleic acids.

Formulas of organic substances by classes

Examples of organic substances

As you remember, in the human body, various kinds of organic substances are the basis of the foundations. These are our tissues and fluids, hormones and pigments, enzymes and ATP, and much more.

In the bodies of humans and animals, proteins and fats are prioritized (half of the dry weight of an animal cell is protein). In plants (about 80% of the dry mass of the cell) - for carbohydrates, primarily complex - polysaccharides. Including for cellulose (without which there would be no paper), starch.

Let's talk about some of them in more detail.

For example, about carbohydrates. If it were possible to take and measure the masses of all organic substances on the planet, it would be carbohydrates that would win this competition.

They serve as a source of energy in the body, are building materials for cells, as well as carry out the supply of substances. Plants use starch for this purpose, and glycogen for animals.

In addition, carbohydrates are very diverse. For example, simple carbohydrates. The most common monosaccharides in nature are pentoses (including deoxyribose, which is part of DNA) and hexoses (glucose, which is well known to you).

Like bricks, at a large construction site of nature, polysaccharides are built from thousands and thousands of monosaccharides. Without them, more precisely, without cellulose, starch, there would be no plants. Yes, and animals without glycogen, lactose and chitin would have a hard time.

Let's look carefully at squirrels. Nature is the greatest master of mosaics and puzzles: from just 20 amino acids, 5 million types of proteins are formed in the human body. Proteins also have many vital functions. For example, construction, regulation of processes in the body, blood coagulation (there are separate proteins for this), movement, transport of certain substances in the body, they are also a source of energy, in the form of enzymes they act as a catalyst for reactions, provide protection. In protecting the body from negative external influences antibodies play an important role. And if a discord occurs in the fine tuning of the body, antibodies, instead of destroying external enemies, can act as aggressors to their own organs and tissues of the body.

Proteins are also divided into simple (proteins) and complex (proteins). And they have properties inherent only to them: denaturation (destruction, which you have noticed more than once when you boiled a hard-boiled egg) and renaturation (this property is widely used in the manufacture of antibiotics, food concentrates, etc.).

Let's not ignore and lipids(fats). In our body, they serve as a reserve source of energy. As solvents, they help the course of biochemical reactions. Participate in the construction of the body - for example, in the formation of cell membranes.

And a few more words about such curious organic compounds as hormones. They are involved in biochemical reactions and metabolism. These small hormones make men men (testosterone) and women women (estrogen). They make us happy or sad (thyroid hormones play an important role in mood swings, and endorphins give a feeling of happiness). And they even determine whether we are “owls” or “larks”. Are you ready to study late or do you prefer to get up early and do homework before school, decides not only your daily routine, but also some adrenal hormones.

Conclusion

The world of organic matter is truly amazing. It is enough to delve into its study just a little to take your breath away from the feeling of kinship with all life on Earth. Two legs, four or roots instead of legs - we are all united by the magic of mother nature's chemical laboratory. It causes carbon atoms to join in chains, react and create thousands of such diverse chemical compounds.

You now have a short guide to organic chemistry. Of course, not all possible information is presented here. Some points you may have to clarify on your own. But you can always use the route we have planned for your independent research.

You can also use the definition of organic matter given in the article, the classification and general formulas of organic compounds and general information about them to prepare for chemistry lessons at school.

Tell us in the comments which section of chemistry (organic or inorganic) you like best and why. Don't forget to share the article in social networks so your classmates can use it too.

Please report if you find any inaccuracy or error in the article. We are all human and we all make mistakes sometimes.

site, with full or partial copying of the material, a link to the source is required.

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"The 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 task, finding out the patterns with which you can determine the desired value on last step computing. 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 fuels, 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 techniques 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 hard 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- coking industry gives whole line medicines(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.