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«Hydrocarbons (Alkanes, Alkenes, Alkynes, Arenes and Their Derivatives) ODESSA NATIONAL MEDICAL UNIVERSITY Department of Clinical Chemistry and Laboratory Diagnostics Bioorganic chemistry Information block for first-year students of medical and dental faculties (Second semester) «Hydrocarbons (alkanes, alkenes, alkynes, arenes and their derivatives). Chemical properties» Test questions: 1. Alkanes. Homological series. Structural isomerism, nomenclature. Chemical properties (SR-reactions). 2. Classification: alkenes, alkynes, alkadienes, types of dienes. Structural and spatial isomerism. Nomenclature. Addition reactions: АЕ, АN- reactions 3. Aromatic hydrocarbons (arenas). Benzene and its homologues. Isomerism of benzene homologs: ortho-, meta- and para- isomers. Nomenclature. 4. General characteristics of the reactivity of benzene. Benzene reactions confirming unsaturated nature, their features. 5. SЕ- reactions of benzene: halogenation, nitration, sulfonation, alkylation, acylation. 1 Alkanes. Cycloalkanes Alkanes are compounds of carbon with hydrogen, in the molecules of which carbon atoms are connected by a single bond (saturated hydrocarbons). The general formula for the homological series of alkanes is СnН2n+2. The radical resulting from the detachment of one hydrogen atom from a saturated hydrocarbon molecule is called an alkylase, the general formula of alkyls is СnН2n+1. The first four members of a number of alkanes have historically established names. Molecular Name Root Hydrocarbon Name formula substituent formula CH4 methane meth- CH3 methyle C2H6 ethane eth- C2H5 Ethyle C3H8 propane prop- C3H7 propyle C4H10 butane but- C4H9 butyle C5H12 pentane pent- C5H11 pentyle C6H14 hexane hex- C6H13 hexyle C7H16 heptane hept- C7H15 heptyle C8H18 octane oct- C8H17 octyle C9H20 nonane non- C9H19 nonyle C10H22 decane dec- C10H21 decyle To give names to alkanes: 1. Choose the longest carbon chain and get the name base. 2. Number the chain so that the substituents get the lowest numbers. 3. In the name, the arabic numerals indicate the position of the deputies, and the prefixes di - 2, tri - 3, tetra - 4, etc. - the number of identical substituents. 4. If there are different substituents, their names are arranged alphabetically, that is, for example, first ethyl, and then methyl. 2,3- dimethylpentane 2 For some branched saturated hydrocarbons, traditional names are used, along with systematic ones, for example, for alkanes of the composition С4Н10 and С5Н12 with the formulas: Physical properties Under standard conditions, the first alkanes — methane, ethane, propane, and butane (С1—С4) —are gases without color and odor, sparingly soluble in water. Subsequent homologues (С5—C15) are liquids (at 20 °C), higher homologues (C16 and higher) are solids. Isomers Alkanes are non-cyclic saturated hydrocarbons. Molecules are long or branched carbon chains. Homologous alkanes can form isomers. The more carbon atoms, the more variants of isomers. The first three alkanes (methane, ethane, propane) do not form isomers. Butane, pentane, hexane have only structural isomers. Butane has two: n-butane and isobutane. Pentane forms n-pentane, isopentane, neopentane. Hexane has five isomers: n-hexane, isohexane, 3-methylpentane, diisopropyl, neohexane. For example, hexane and its isomers. In alkanes, carbon atomic orbitals have sp3 hybridization; four electron clouds of the carbon atom are directed to the vertices of the tetrahedron at angles of 109.5 °. The covalent bonds formed by each carbon atom in the alkanes are not polar. 3 Therefore, alkanes, which are comparatively inert substances, enter only substitution reactions proceeding with a symmetric (radical) cleavage of С – Н bonds. These reactions usually occur in harsh conditions (high temperature, lighting). As a result, it becomes possible to replace hydrogen with halogen (Cl, Br) and nitro group (NO2), for example, when methane is treated with chlorine in the presence of a light quantum: The second and subsequent stages of the reaction proceed more easily than the first, due to a shift in the electron density to the chlorine atom: and an increase in the mobility of the remaining hydrogen atoms. Product names: CH3Cl - chloromethane, CH2Cl2 - dichloromethane, CHCl3 - trichloromethane (chloroform), СCl4 - carbon tetrachloride (carbon tetrachloride). The Konovalov’s reaction. Alkanes react with diluted nitric acid under heating and pressure. As a result, the hydrogen atom is replaced by the remainder of nitric acid - the nitro group NO2. This reaction is called the nitration reaction, and the products of the reaction are called nitro compounds. The reaction scheme: When nitration of alkanes, the order of the reactivity of C-H bonds, characteristic of radical substitution reactions, is also observed: Сtert.– Н > Сsec– Н > Cprim– Н For example: 4 Combustion and oxidation. The process of burning hydrocarbons is widely used to generate energy (in internal combustion engines, in thermal power plants, etc.). The equation of the reaction of combustion of alkanes in general form: From this equation it follows that with an increase in the number of carbon atoms (n) in the alkane, the amount of oxygen necessary for its complete oxidation increases. The lower homologues (methane, ethane, propane, butane) form explosive mixtures with air, which must be taken into account when using them. During the combustion of higher alkanes (n >> 1), the oxygen contained in the air may not be enough for their complete oxidation to CO2. Then the products of partial oxidation are formed: carbon monoxide CO (oxidation state of carbon +2), carbon black (fine carbon, zero oxidation state). Therefore, higher alkanes burn in the air with a smoky flame, and the emission of toxic carbon monoxide (odorless and colorless) is dangerous to humans. Combustion of methane with a lack of oxygen occurs according to the equations: The last reaction is used in industry to produce carbon black from natural gas containing 80-97% methane. Partial oxidation of alkanes at a relatively low temperature and with the use of catalysts is accompanied by the breaking of only part of the C – C and C – H bonds and is used to produce valuable products: carboxylic acids, ketones, aldehydes, alcohols. For example, with incomplete oxidation of butane (C2 – C3 bond cleavage), acetic acid is obtained: butane acetic acid 5 Higher alkanes (n> 25) under the influence of atmospheric oxygen in the liquid phase in the presence of manganese salts turn into a mixture of carboxylic acids with an average chain length of С12–С18, which are used to obtain detergents and surfactants. The reaction of methane interaction with water vapor is of great importance, as a result of which a mixture of carbon monoxide (II) with hydrogen is formed - "synthesis gas": This reaction is used to produce hydrogen. Synthesis gas serves as a raw material for the production of various hydrocarbons. Alkenes. Alkadienes Alkenes (olefins) are hydrocarbons whose molecules contain carbon atoms interconnected by a double bond (unsaturated hydrocarbons of a number of ethylene). The simplest representative is ethylene С2Н4, the general formula for the homologous series of ethylene hydrocarbons СnН2n. The systematic names of olefins are derived from the roots of the names of alkanes with the replacement of the suffix -ane to -ene: C2H4 - Ethene C6H12 - Hexene C3H6 - Propene C7H14 - Heptene C4H8 - Butene C8H16 - Octene C5H10 - Pentene C9H18 - Nonene The position of the double bond C = C in the isomers of the structure (starting from C4 alkene) indicates the number after the name: but-1-ene but-2-ene Another type of isomerism in unsaturated hydrocarbons, in addition to structural isomerism, is because the carbon atoms forming the double bond are in the sp2 hybrid state; The π-component of the C=C double bond and the C–H double bond lie in the same plane at an angle of 120° to each other, and the σ component of the C=C double bond is an electron cloud elongated in the direction perpendicular to the 6 plane of the σ-bonds. The consequence of this structure of alkenes is the possibility of geometric isomerism (or cis-trans isomerism) depending on the position of the substituents (atoms or radicals): cys-but-2-ene trans - but-2-ene (cis - from lat. "nearby, on one side", trans - from lat. "opposite, on opposite sides"). Alkenes C2 - C4 at room temperature are colorless gases with a faint smell of oil, sparingly soluble in water; C5 - C18 alkenes are liquids; C19 alkenes and higher are solids. The most important chemical properties of alkenes are determined by the fact that, due to the lower strength of the π-bond (as compared to the σ-bond), it easily breaks, as a result of which addition reactions occur and saturated organic compounds are formed. As a rule, such reactions proceed under mild conditions, often in the cold and in solvents, for example, water, carbon tetrachloride СCl4, etc.: propene 1,2-dibromopropane The interaction of alkenes with hydrogen bromide proceeds similarly: ethene dibromoethane The addition of hydrogen halides to asymmetric alkenes can theoretically lead to two products: According to Markovnikov’s rule, the addition of hydrogen halides to asymmetric alkenes proceeds so that the hydrogen is directed to the carbon atom, which already contains a larger number of hydrogen atoms. In the above reaction, the product will be 2-iodopropane CH3CH(I)CH3. 7 According to Markovnikov’s rule, a hydration reaction also takes place, i.e., a water addition reaction in the presence of sulfuric acid. It occurs in two stages: a) first, alkylsulfuric acid is formed,
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