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Organic Chemistry: Hydrocarbon

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Further explanation in Alkene and alkane with the reaction mechanism involved.

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Organic Chemistry: Hydrocarbon

  1. 1. CHEMISTRY FORM 6 ORGANIC CHEMISTRY CHAPTER 2 : HYDROCARBON
  2. 2. 2.1 Nomenclature of ALKANE Alkane is a saturated hydrocarbon as it contain only single bond in its molecule General formula for homologous series of alkane is CnH2n+2 Table below shows the naming of straight chain of alkane Hydrocarbon which contain only carbon-carbon single bond, C–C Hydrocarbon which contain at least one carbon-carbon double bond, C=C or triple bond, C≡C
  3. 3. Name Molecular formula Molecular structure Name Molecular formula Molecular structure Methane CH4 Ethane C2H6 Propane C3H8 Butane C4H10 Pentane C5H12 Hexane C6H14
  4. 4. 2.2 Naming alkane according IUPAC Step 1 Step 2 Step 3 Step 4 Find the longest chain of carbon and name accordingly. (it does not has to be a straight chain). Identify the ‘branched’ carbon (alkyl group) that attached to the ‘main’ chain. Then, name the alkyl accordingly CH3– methyl CH3CH2– ethyl CH3CH2CH2-propyl Place a prefix upon the similar alkyl group (if any). If there is 2 similar alkyl, prefix di is placed, if 3 similar alkyl, prefix tri is placed. State the position where the ‘branch’ is located at which carbon based on the numbering gave earlier.
  5. 5. CH3(CH2)5CH3 CH(CH3)2C(CH3)3 CH3CH(CH2CH3)2 C(CH3)3CH2C(CH3)3 2,3-dimethylpentane 3-ethyl-3- methylhexane 2,2,3-trimethylpentane 3,3-diethylhexane 3-methylpentane 3,5-dimethylheptane 3-ethyl-4-methylhexane 3-ethyl-3,5- dimethyloctane n-heptane 2,2,3-trimethylbutane 3-methylpentane 2,2,4,4- tetramethylpentane
  6. 6. Step 3 Complete the structure by placing one hydrogen (H) atom at each of single bonds.
  7. 7. Isomer of hexane, C6H14
  8. 8. 2.4 Physical properties of alkane Alkane CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 Boiling point oC – 162 – 8.6 – 42.2 – 0.5 36.3 68.7 98.4 126 Boiling point trend Density (g/cm3) -- -- 0.50 0.58 0.63 0.66 0.68 0.70 Density trend Solubility Not soluble in .. Soluble in BOILING POINT INCREASE DOWN HOMOLOGOUS SERIES DENSITY INCREASE DOWN HOMOLOGOUS SERIES water organic solvent
  9. 9. A) Boiling point of alkenes The boiling point when going down to homologous series of alkane. All alkane possessed the same intermolecular forces : weak forces Greater the , stronger the forces, the boiling point Boiling point of isomers of the same molecular formula varies with the branched molecules Straight chain has .. .. boiling point compared to branched chain as straight chain molecule has higher compared to a branched chain. The positioning of alkyl and number of alkyl also effect the boiling point of alkane. 2-methylpentane as a higher boiling point than 3-methylpentane as it has a greater exposure of intermolecular forced increase Van Der Waals molecular mass weak Van Der Waals’ increase higher total surface area
  10. 10. B) Solubility of alkane All alkanes are often consider as molecule as the dipole of moment created in molecule is very small. Since alkane is . Molecule, it dissolve easily in non-polar solvent such as benzene, and ether. Alkane does not form bond in water, so it is in water. Thus, alkane is also described as . (water–hating). The longer the alkane chain, the more insoluble it is in water. non-polar non-polar hydrogen insoluble hydrophobic
  11. 11. 2.5 Chemical Properties of Alkane 2.5.1 Preparation of Alkane Alkane can be prepared using the following methods : Decarboxylation of sodium salt of a carboxylic acid R–COOH + NaOH → R–H + Na2CO3 Example : Kolbe’s method : electrolysing concentrated sodium ethanoate Cathode : 2 H2O + 2 e- H2 + 2 OH- Anode : 2 CH3COO- C2H6 + 2 CO2 + 2 e- Wurtz reaction : reaction of sodium on alkyl halide in ether. 2 R–X + 2 Na R – R + 2 NaX Example CH3COOH + 2 NaOH CH4 + H2O + Na2CO3 2 CH3CH2–Cl + 2 Na CH3CH2CH2CH3 + 2 NaCl
  12. 12. 2.5.2 Reaction of Alkane Since alkane is a . hydrocarbon, so alkane is inert to most of the chemical reaction Table below shows the description of reaction of ethane with other substances. From the series of reaction above it can be conclude that Ethane does no react with polar or ionic substances Ethane react with non-polar substances such as Cl2 , Br2 and O2 and energies are required for reaction to occur. Reagents Effect on ethane Sodium hydroxide aqueous No effect on hot or cold condition Concentrated hydrochloric acid No effect on hot or cold condition Acidified potassium manganate (VII) No effect on hot or cold condition Air (oxygen) No effect under room condition. Burns when heated Bromine water No effect on dark. Decolourised slowly under sunlight Chlorine gas No effect on dark. Reaction occur under sunlight saturated
  13. 13. 1. Combustion of alkanes All hydrocarbon react with oxygen to form carbon dioxide and water. The equation for a complete combustion for all hydrocarbons can be represented by the equation C2H6 C5H12 C8H18 Note that the reaction is exothermic for all hydrocarbons. Equation above is also known for ∆Hc. Higher the number of carbon, the more exothermic the reaction. Under limited supply of air (oxygen), sometimes, carbon monoxide (CO) is produced instead of CO2. mol/kJmHOH 2 y COxO 4 y xHC 222yX −=∆+→      ++ C2H6 + 7/2 O2 2 CO2 + 3 H2O C5H12 + 8 O2 5 CO2 + 6 H2O C8H18 + 25/2 O2 8 CO2 + 9 H2O
  14. 14. 2.Halogenation of alkanes When alkane is run together with chlorine gas under the presence of ultraviolet ray (which comes naturally from sunlight) Example : CH4 (g) + Cl2 (g) CH3Cl (g) + HCl (g) C2H6 (g) + Cl2 (g) The mechanism for the reaction of chlorination of alkane can be explained using the following steps Step 1 : Initiation Step 2 : Propagation Step 3 : Termination Cl – Cl 2 Cl• ∆H = +242 kJ/mol H3C–H CH3• + H• ∆H = + 433 kJ/mol Since ...................... required lower energy to form radical, so the initiation will start off with .. Gas Since chlorine radical are highly reactive, when it collide with methane molecule forming HCl and methyl radical H3C–H + •Cl H3C• + HCl Methyl radical will propagate with other chlorine molecule and forming back chlorine radical H3C• + Cl–Cl H3CCl + •Cl Under such propagation reaction thousands of methane and chlorine molecules will react continuously When 2 free radicals collide with each other and combined, the reaction stops. This reaction is highly exothermic, where H3C• + •Cl H3C–Cl ∆H = -349 kJ/mol H3C• + •CH3 H3C–CH3 (H = -368 kJ/mol Usually, termination will occur when [radical] > [molecule], which is after thousands of propagation. The presence of small amount of ethane may also present due to the collision between 2 methyl radicals chlorine chlorine
  15. 15. 2.1.1 Sources of hydrocarbon The main sources of hydrocarbons are : a) crude oil b) coal c) natural gas Since all these main sources are made up from dead animals and plants, so they are also known as Coal is complex mixture consisting mainly hydrocarbons, which is mainly made up from dead plaints in swamp. Petroleum is a mixture of hydrocarbons (alkanes, alkenes, alkyne), while natural gas contain mainly . and some The mixture in petroleum can be separated by using . in oil refinery. Diagram below shows the chamber and oil refinery used to separate the mixture of petroleum. fossil fuel methane ethane fractional distillation
  16. 16. Fractional distillation Products Uses Petrol gas Use for house cooking gas Gasoline Use as fuel for automobile vehicle Naphtha Use to synthesis different petrochemical Diesel oil Use as fuel of heavy vehicle such as bus or lorry Kerosene Use as fuel for jet engine and oil stove Lubricant Oil Use for lubrication, making wax and polish Fuel Oil Fuel for ship and power station Bitumen (asphalt) Use as tar for paving road surface and coating underground water pipe
  17. 17. The separation does not end with fractional distillation. They are then treated with various ways to improve the quality and quantity of useful hydrocarbon. One of the major treatments gives after fractional distillation is cracking process. Cracking of hydrocarbon Thermal cracking (Pyrolysis) Catalytic cracking Using high temperature, bond breaking (homolytic fission) take place and form various products of unbranched alkane and alkene Example, when breaking decane, C10H22 C10H22 → C3H6 + C7H16 C10H22 → C4H8 + C6H14 With the aid of zeolite as catalyst, carbon cracking can occur at lower temperature compare to thermal cracking. Products using catalytic cracking usually contain branched alkane and alkene. C10H22 →
  18. 18. 2.7 Cycloalkane (alicyclic compound) Cycloalkane has a general formula of CnH2n Some examples of cycloalkane Cycloalkane Molecular formula Displayed formula Skeletal formula Cyclopropane Cyclobutane Cyclopentane Cyclohexane C3H6 C4H8 C5H10 C6H12
  19. 19. 2.7.1 Naming cycloalkane The way of naming cyclolalkane is more or less the same with naming alkane. If theirs is one alkyl attached to the cycle, it will be automatically become ‘1’ by itself. E.g. methylcyclobutane (not “1-methylcyclobutane) If there’s more than one “group” attaching the cycle, only then numbering will be given to the particular number of C that it is attached. methylcyclopropane 3-ethyl-1-methylcyclopentane 1,2,4-trimethylcyclohexane 1,2,3-trimethylcyclooctane 3-ethyl-2-methyl-1- propylcyclobutane
  20. 20. 2.7.2 Preparation and Reaction of Cycloalkane Cycloalkane can be prepared by catalytic hydrogenation of benzene at 200oC Reaction of cycloalkane is similar to alkane. When react with chlorine / bromine gas under sunlight, substitution reaction take place Mechanism : Initiation Propagation Termination
  21. 21. 2.8 Alkene – Nomenclature of alkenes and cycloalkenes The homologous series of alkenes has general formula of CnH2n. The significance of alkene is all of them have C=C in their molecules with its name end with –ene Name Molecular formula Molecular structure Name Molecular formula Molecular structure Ethene C2H4 Propene C3H6 Butene C4H8 Pentene C5H10 Hexene C6H12 But-2-ene But-1-ene pent-2-ene pent-1-ene Hex-1-ene Hex-2-ene Hex-3-ene
  22. 22. In naming alkene, the following steps are given Step 1 : Find the longest C – C chain which contain double bond in it (parent chain) and name them Step 2 : Find and name the alkyls attached to the parent chain. Step 3 : If there are more than 2 of the same type alkyls, prefix are put accordingly. Step 4 : Put the number of the alkyl that attached to the particular carbon atom. Example : Name the following alkenes accordingly
  23. 23. 2-methylbut-2-ene 2-ethyl-3-methylpent-1-ene 3,4-dimethylhex-3-ene 2-methylpropene 2,3-dimethylpent-2-ene 3,5-dimethylhept-3-ene
  24. 24. 2.8.1 Naming alkene with more than one single bond & cycloalkene A “diene” (alkene with 2 C=C bond) and cycloalkene has general formula of CnH2n–2. In diene, the position of both C=C in parent chain has to be stated in alkan- x,y-diene, whereas in cycloalkene, C=C is always place as C1=C2. So the numbering is fixed for naming. Example, name the following diene / cycloalkene below 2-methylbut-1,3-diene 2,5-dimethylhex-1,3-diene oct-2,5-diene 3-methylcyclopropene 3-ethyl-2-methylcyclohexene 3,4,5-trimethylcyclopentene
  25. 25. 2.9 Isomerism in alkene. Alkenes which contain at least 4 Carbon atoms may exhibit 2 isomerism, structural and stereoisomerism. For example, butane (C4H8) contain 5 isomers.
  26. 26. Isomers of pentene
  27. 27. 2.10 Physical Properties of Alkene A) Boiling Point of Alkene The boiling point when going down to homologous series of alkane. All alkane possessed the same intermolecular forces : weak forces Greater the .., stronger the forces, the boiling point Alkene C2H4 C3H6 C4H8 C5H10 C6H12 C7H14 C8H16 C9H18 Boiling point oC – 164 – 12.0 – 5.8 – 0.5 38.0 72.07 96.5 117 Boiling point trend Solubility in water Boiling point increase Insoluble in water (solubulity decrease) increase Van Der Waals molecular mass weak Van Der Waals higher
  28. 28. 2.11 Preparation of Alkene Alkene can be prepared in a few ways Name of reaction Reagent used and condition Equation Dehydro- halogenation from haloalkane Ethanolic sodium hydroxide (heat & reflux) Dehydration (removal of water) from alcohol Excess conc. H2SO4 at 1800C or Alumina (Al2O3) at 350oC
  29. 29. 2.12 Chemical reaction of alkene Name of reaction Reagent used and condition Equation Hydrogenation Hydrogen gas under -------------- Nickel (Ni) at 180oC @ Platinum (Pt) at room temperature CH3CH=CH2 + H2 (g) CH3CH2CH3 (g) propene propane cyclohexene cyclohexane Halogenation Halogen gas, X2 (X2 = Cl2 ; Br2 ; I2) Addition of Hydrogen halide Hydrogen halide ( H – X ) (X = Cl ; Br ; I) Ni
  30. 30. Name of reaction Reagent used and condition Equation Hydration Steam (H2O) --------- Phosphoric acid, (H3PO4 ) At 300oC ; 60 atm Hydroxylation (cold, diluted acidified KMnO4) KMnO4 (aq) / H+ (cold and diluted) Oxidation (under hot, concentrated acidified potassium manganate (VII) KMnO4 (aq) / H+ (hot & concentrated)
  31. 31. 2.12 Chemical reaction (1) Hydrogenation of alkene Carry out under mixture of alkene and hydrogen over a finely divided transition metal as a catalyst. 2 catalysts can be used in hydrogenation i) Platinum : ~ can react even under room condition. Longer alkene required some heat ii) Nickel : ~ required high temperature to allow hydrogenation to occur (180oC) Hydrogenation is an exothermic reaction and its ∆H is about –120 kJ / mol CH3CH=CH2 (g) + H2 (g) CH3CH2CH3 ∆H = –124 kJ / mol Catalytic hydrogenation is important in food industries especially in hardening unsaturated fats and oil to make margarine. Unsaturated hydrocarbon makes them too soft for commercial use. CH3(CH2)7CH=CH(CH2)7COOH + H2 (g) CH3(CH2)16COOH In industries, a special “Raney Catalyst” is used to replace platinum as it is EXPENSIVE!!!
  32. 32. (2) Halogenation of alkene Chlorine and bromine react readily with alkene and form dichloroalkane and dibromoalkane respectively. Cl2 and Br2 gas are add across double bond. CH3CH=CH2 (g) + Cl2 (g) CH3CH(Cl)CH2Cl The mechanism of halogenation can be explained by a few steps describe below : Step 1 : Formation of carbocation – propene has region of high electron density because of the π electron. When Cl2 approaches, molecule is strongly polarised by region and consequently formed an induce dipole. The positive charge end of Cl2 molecule act as electrophile and bond to C=C via electroplilic addition and caused Clδ+–Clδ− repelled. As a result, carbocation & chloride ion are formed.
  33. 33. Step 2 : Nucleophilic attack to form addition product – carbocation formed is very unstable. It quickly combines with Cl− ion to produce by heterolytic fission of Cl2 molecule to give 1,2-dichloropropane. However, if bromine water is used instead of bromine gas, the results of products are not as same as in bromine gas. When bromine water is reacted with propene
  34. 34. (3) Addition of hydrogen halide Unlike addition of halogen, addition of hydrogen halide produced 2 products. For example, when propene react with hydrogen bromide (H–Br) CH3CH=CH2 + H–Br CH3CH2CH2Br + CH3CH(Br)CH3 Propene 1-bromopropane 2-bromopropane (minor) (major) The major / minor product of the reaction can be predicted using Markovnikoff’s Rule where it stated when an unsymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the carbon that has the greater number of hydrogen substituents, and the halogen adds to the carbon having fewer hydrogen substituents.
  35. 35. Step 1 : Electrophilic attack – when the polar hydrogen bromide approaches propene, the positively charged hydrogen ion is polarising C=C, and caused Br− to form Step 2 : Nucleophilic attack – the negative bromide ion react fast with the unstable carbocation. δ+ δ–
  36. 36. Relative stability of carbocation can be explained using Markovnikoff’s Rule. According to the rule, a tertiary (30) carbocation is more stable than a secondary (20) carbocation than a primary (10) carbocation. this is due to the inductive effect of the electron-donating alkyl group. In the example above, there are 2 methyl group donating electron to positive charged carbon electron at 20 carbocation whereas there are 1 ethyl group in 10 carbocation donating electron to the positively charged electron. As a result, 20 carbocation are more stable as the 2 alkyl group tend to decrease the charge density of C, making the cation more stable. stability of carbocation increase.
  37. 37. (4) Hydration (addition of water) in alkene Using phosphoric acid as acidic medium, hydration of alkene can be represent by equation : CH3C(CH3)=CH2 + H–OH CH3CH(CH3)CH2OH + CH3C(CH3)(OH)CH3 (minor) (major) 2-methylpropene 2-methylpropan-1-ol 2-methylpropan-2-ol Similar to hydrogen halide, hydration of alkene follows Markovnikoff’s Rule. The mechanism of hydration of alkene is slightly different from addition of hydrogen halide Step 1 : Protonation of the carbon–carbon double bond in the direction that leads to the more stable carbocation
  38. 38. Step 2 : Water acts as a nucleophile to capture carbocation Step 3 : Deprotonation of tert-butyloxonium ion. Water acts as a Brønsted – Lowry base: Other than using diluted acid medium, sometimes, hydration of alcohol is prepared by adding concentrated sulphuric acid to alkene. When H2SO4 (conc) is added to alkene under room condition, it give an alkyl hydrogensulphate
  39. 39. Hydrolysis of alkyl hydrogensulphate will convert into alcohol
  40. 40. (5) Oxidation of alkene using acidified potassium manganate (VII) Alkene are readily oxidised by acidified KMnO4 (decolourised the purple colour of KMnO4) and give different products under different condition If cold diluted acidified KMnO4 is used, a diol is given as a product. If hot concentrated acidified KMnO4 is used, a ketone or an aldehyde is formed which will further oxidised to become a carboxylic acid or into carbon dioxide and water depend on alkene. a) Hydroxylation of alkene (react under cold dilute acidified KMnO4) The product of this reaction is a diol (di-alcohol) – which contain 2 hydroxyl group. This reaction is often used to distinguish between saturated hydrocarbon and unsaturated hydrocarbon (alkane and alkene)
  41. 41. b) Oxidation of alkene using hot, concentrated acidified potassium manganate (VII) When alkene react with hot concentrated acidified potassium manganate (VII), it will oxidise immediately to form aldehyde or ketone, depend on the type of alkene Using this method, the position of C=C in alkene can be deduced. If the alkene is a 10 alkene, it will turn lime water chalky when the particular alkene is reacted with hot concentrated acidified potassium manganate (VII)
  42. 42. Alkene Products methanal Methanoic acid
  43. 43. a.CH3CH2CH=CHCH3 + H2 (g) b.CH3CH2CH=CH2 + Cl2 (g) c. CH3CH=C(CH3)CH3 + Br2 (l) d.CH3CH(CH3)CH=CH2 + HCl (g) CH3CH2CH2CH2CH3 CH3CH2CHClCH2Cl CH3CHBrC(CH3)(OH)CH3 major CH3CHBrCBr(CH3)CH3 minor CH3CH(CH3)CHClCH3 major CH3CH(CH3)CH2CH2Cl minor
  44. 44. 4-ethyl-2,2,4-trimethylhexane 2,2,4,5-tetramethylhexane 5-ethyl-3,4-dimethyloctane
  45. 45. 2,3,4,6,6-pentamethyl-3-heptene 7-ethyl-1,3-dimethylcyloheptene C(CH3)2=C(CH2CH3)CH(CH3)CH(CH3)2 CH2=CHC(CH3)(CH2CH3)C(CH3)=CH2
  46. 46. Isomers of pentene
  47. 47. Practice : Write the chemical equation for the following reaction 1.Butane react with chlorine under the presence of sunlight CH3CH2CH2CH3 + Cl2 → CH3CH2CH2CH2Cl + HCl 2.Pentane burned with excess air C5H12 + 8 O2 → 5 CO2 + 6 H2O 3.Octane burned with excess air C8H18 + 25 / 2 O2 → 8 CO2 + 9 H2O 4.Propene reacts with hydrogen gas using platinum as catalyst CH3CH=CH2 + H2 → CH3CH2CH3 5.1-hexene burned with excess air C6H12 + 9 O2 → 6 CO2 + 6 H2O 6.2-heptene reacts with bromine water CH3CH2CH2CH2CH2CH=CH2 + Br2 + H2O → CH3CH2CH2CH2CH2CH(OH)CH2Br + CH3CH2CH2CH2CH2CHBrCH2Br 7.Propene reacts with hydrogen chloride CH3CH=CH2 + HCl → CH3CH2CH2Cl (min) + CH3CHClCH3 (maj)
  48. 48. 8.1-Butene react with excess oxygen C4H8 + 6 O2 → 4 CO2 + 4 H2O 9.2-Pentene reacts with steam catalysed by sulphuric acid CH3CH=CHCH2CH3 + H2O →CH3CH(OH)CH2CH2CH3 CH3CH2CH(OH)CH2CH3 10. 3-Hexene reacts with cold dilute acidified KMnO4 CH3CH2CH=CHCH2CH3 + KMnO4/H+ → CH3CH2CH(OH)CH(OH)CH2CH3 11. 2-methylhex-2-ene reacts with cold dilute acidified KMnO4 CH3C(CH3)=CHCH2CH2CH3 + KMnO4/H+ → CH3C(CH3)(OH)CH(OH)CH2CH2CH3 12. Propane react with fluorine under the presence of sunlight CH3CH2CH3 + F2 → CH3CH2CH2F + HF 13. Propene is polymerized at 2000C and 1200 atm 14. 2-methylbut-2-ene react with bromine water under the presence of sunlight.
  49. 49. 4. Proposed the mechanism for the following reaction below

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