Hydrocarbons. Vladimíra Kvasnicová
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1 Hydrocarbons Vladimíra Kvasnicová
2 Electron configuration of carbon atoms position of carbon in the Periodic table of elements: 2 nd period, group IVA 6 C 6 p+ 6 e - orbitals: 1s 2 2s 2 2p 2 (4 valence e - ) electrons in different orbitals have different energy (it rises in the order: 1s < 2s <2p) electrons in s-orbitals move in a spherical space electrons in p-orbitals move in a space of 2 opposite drops electrons of a separate carbon atom and a carbon found in a molecule are arrangend differently: the process of hybridization changes energy of electrons example: sp 3 hybridization = s p x p y p z orbitals have the same energy
3 hydrogen atom (H): 1s 1 Bonds in hydrocarbons 1 electron of hydrogen and 1 electron of carbon make pair of electrons: covalent bond (sharing electrons) pairing of electrons from s-orbitals (or hybride orbitals) makes sigma-bond (σ-bond) sigma electrons move around the axis connecting two atoms involved in a covalent bond (H-C or C-C) pairing of electrons from p-orbitals makes pi-bond (π-bond) pi electrons moveabove and under the axis connecting two atoms (C-C) they are more reactive double bond = 1 σ-bond and 1 π-bond triple bond = 1 σ-bond and 2 π-bonds
4 Shape of molecules σ-bond C-C π-bond C=C C C Alkanes hybridization sp 3 tetrahedral shape (4 σ bonds) ethane
5 Alkenes hybridization sp 2 trigon (each carbon: 3 σ and 1 π) Alkynes ethene hybridization sp linear (each carbon: 2 σ and 2 π) ethyne
6 Alkanes saturated hydrocarbons (C n H 2n+2 ) main natural source: natural gase (up to 97% of methane; ethane, propane, CO 2, N 2 ) petroleum (mixture of aliphatic, alicyclic, and polycyclic hydrocarbons C 1 -C 50 ; the composition varies with its location)
7 Alkanes saturated hydrocarbons (C n H 2n+2 ) fractions of petroleum: gas (C1-C4) ~ cooking gas petroleum ether (C5-C6) ~ solvent for org. chemicals gasoline (C6-C12) ~ automobile fuel kerosene (C11-C16) ~ rocket and jet fuel fuel oil (C14-C18) ~ domestic heating lubricating oil (C15-C24) ~ lubricants for automobiles and machines
8 Alkanes saturated hydrocarbons (C n H 2n+2 ) methane ethane hexane 3-methylpenthane! Alkanes are not planar!
9 Alkanes saturated hydrocarbons (C n H 2n+2 ) physical properties: not soluble in water (= hydrophobic) non polar bonds (similar electronegativity of C and H) densities between 0.6 and 0.8 g/cm 3 (= less than water) colorless, tasteless, nearly odorless boiling points increase with increasing MW, and decrease with branching (C1-C4 are gases) volatility decreases with molar weight (MW) narcotic and irritant effects increase with MW (! C5-C9)
10 Alkanes saturated hydrocarbons (C n H 2n+2 ) alkanes and the human body: inhalation of alkane vapors (e.g. gasoline) causes severe damage to the lung tissue (it dissolves cellular membranes) liquid alkanes can also harm the skin: long-term contact between low MW alkanes and skin remove skin oils and can cause soreness and blisters high MW alkanes can be used to protect the skin: mixtures of C 20 -C 30 alkanes are used in skin and hair lotions to replace natural oils mineral oil purified mixture has been used as a laxative
11 reactivity: Alkanes saturated hydrocarbons (C n H 2n+2 ) not very reactive ( paraffins ~ parum affinis = little activity) simple (sigma, σ) bonds: C-C bonding electrons tightly held between carbons, not readily available to other substances C-H bonds around the carbon skeleton, more susceptible to reactions (usually under extreme conditions)
12 Alkanes saturated hydrocarbons (C n H 2n+2 ) reactivity: 1. oxidation (combustion) gases of any alkane form explosive mixtures with air exergonic reaction: heat is produced e.g. CH 4 + 2O 2 CO 2 + 2H 2 O + energy (192 kcal) 2. halogenation (it is a substitution reaction, replacement) CH 4 + Cl 2 CH 3 Cl + HCl CH 3 Cl + Cl 2 CH 2 Cl 2 + HCl... CHCl 3, CCl 4
13 Cycloalkanes cyclic saturated hydrocarbons (C n H 2n ) carbon atoms in a ring (polygon) properties similar to alicyclic hydrocarbons C3 and C4 are higly reactive (ring strain) cyclopropane was used as a narcotics polycyclic (cyclopentano perhydrophenanthrene) is a parent structure of steroids C3, C4, C5 are planar molecules
14 Cycloalkanes cyclic saturated hydrocarbons (C n H 2n ) C6: many conformations in space (free rotation of C-C; the most stable at room temperature: CHAIR conformation) hem539/answers/chexane_chair.jpg m/chemistry/students/williamso n/stewart/chairboat.jpg
15 Cycloalkanes cyclic saturated hydrocarbons (C n H 2n ) geometric isomerism = the same sequential arrangement of atoms but different arrangement in space trans = E- cis = Z-
16 Alkenes unsaturated hydrocarbons (C n H 2n ) physical properties: not soluble in water (= hydrophobic) nonpolar bonds (similar electronegativity of C and H) low boiling points lower than alkanes of the same length (C2-C4 are gases) double bond consist of 1σ and 1π bond the double bond does not permit free rotation geometric isomerism
17 Alkenes unsaturated hydrocarbons (C n H 2n ) ethene (= ethylene) is planar
18 Alkenes unsaturated hydrocarbons (C n H 2n ) example of geometric isomers:
19 Alkenes unsaturated hydrocarbons (C n H 2n ) alkenes have higher biological efect than alkanes their narcotic efect and toxicity increase with MW and with other unsaturated bonds 2 double bonds: ALKADIENS polyisoprene (natural rubber) 2-methylbuta-1,3-diene = isoprene
20 Alkenes unsaturated hydrocarbons (C n H 2n ) reactivity: the double bond is responsible for their reactivity 1. oxidation - π-bond is attacked by oxidizing agents CH 3 -CH=CH-CH 3 CH 3 -CH(OH)-CH(OH)-CH 3 (e.g. by KMnO 4 ) 2. reduction = hydrogenation = saturation of the molecule by hydrogen (hydrogenation is a kind of addition reaction) CH 3 -CH=CH-CH 3 + H 2 CH 3 -CH 2 -CH 2 -CH 3 (catalyzed by Pt)
21 Alkenes unsaturated hydrocarbons (C n H 2n ) reactivity: 3. addition reaction = two substances join together to form a compound containing all atoms present in the original substances the double bond is transformed to the single bond, substituents are added CH 2 =CH 2 + Br 2 Br-CH 2 -CH 2 -Br CH 2 =CH 2 + HCl CH 3 -CH 2 -Cl CH 2 =CH 2 + H 2 O CH 3 -CH 2 -OH = halogenation = halogenation = hydration
22 Alkenes unsaturated hydrocarbons (C n H 2n )! Markovnikov s rule! for unsymmetrical reagents HX hydrogen atom of the reagent HX binds to the unsaturated carbon that has the greater number of dirrectly bonded hydrogen atoms anicprops/alkenes/propenehcl.gif
23 Alkenes unsaturated hydrocarbons (C n H 2n ) 4. polymerization polymers are high molecular weight molecules made from thousands of repeating units, which are low molecular weight molecules ( monomers ) it is a multiple addition reaction of alkenes e.g. n CH 2 =CH 2 (-CH 2 -CH 2 -) n properties of polymers depend on the monomer used and MW of the product
24 Alkenes unsaturated hydrocarbons (C n H 2n ) 4. polymerization - examples of polymers: polyethylene (PE) polyvinylchloride (PVC) polypropylene (PP) polytetrafluoroethylene (Teflon) polystyrene (PS) polymethylmetacrylate (Plexiglas)
25 Alkynes unsaturated hydrocarbons (C n H 2n-2 ) physical properties: boiling points slightly higher than that of alkanes and alkenes specific gravity higher in comparision to alkenes the triple bond = 1σ and 2π bonds it is shorter than the double bond the reactivity of the triple bond is similar to that of the double bond of alkenes (addition reactions) ethyne (= acetylene): all four atoms in a straight line
26 benzene Aromatic hydrocarbons liquid of pleasant odour narcotic effect can damage the bone marrow (it can give rise to leukemia) toluene and xylenes narcotic and irritant effect less dangerous than benzene
27 biphenyl Aromatic hydrocarbons suspected from cancerogenesis naphtalene irritant effect (skin, mucosa) causes methemoglobinemia and the kidney damage benzo(a)pyrenes cancerogenic effect
28 Halogene Derivatives majority of gas or liquid halogene derivatives: narcotic effect irritate skin and mucosa some can cause liver and nervous system damage solvents (CCl 4, CCl 3 CH 3, CCl 2 =CCl 2 ) cooling media (CH 3 Cl, freons, e.g. CCl 2 F 2 ) fire-extinguishing agents (CCl 4, CBrF 3,...) insecticides (DDT, C 6 H 6 Cl 6 )
29 monomers Halogene Derivatives CF 2 =CF 2, CH 2 =CHCl, chloroprene: CH 2 =CH(Cl)CH=CH 2 polychloroprene = NEOPRENE anesthetics (Halothane: CF 3 CHClBr) formerly used in the medicine: bromoform (in cough sirups), iodoform (desinfectant) polychlorinated biphenyls (PCB)
30 Important common (trivial) names - add structural formulas - ethene = ethylene ethyne = acetylene trichloromethane = chloroform chloroethene = vinylchloride 2-methylbut-1,3-diene = isoprene methylbenzene = toluene dimethylbenzenes = xylenes vinylbenzene = styrene MEMORIZE THESE NAMES
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