Hydrocarbons

Adhiyoga S. (1) Cornellius K. (5) X-10

What is Hydrocarbon? First, lets talk about Carbon compound. Long time ago people thought that Carbon is come from living things (plant, animal, human, etc). Along with the increasement of science, they found two types of Carbon: a. Inorganic Carbon Compound Ex: H2CO3, HCN b. Organic Carbon Compound One of Organic Carbon Compound is Hydrocarbon Then, what is Hydrocarbon? Hydrocarbons is components that composed of Carbon and Hydrogen Classification of Hydrocarbon Based on the shape of the molecular structure can be generated by combining the electrons in the valence shell of a neutral carbon atom with hydrogen atoms to form a compound in which the carbon atom shares a total of valence electrons. There are Aliphatic Hydrocarbon, Alicyclic Hydrocarbon, Aromatic Hydrocarbon 1. Aliphatic Hydrocarbon An aliphatic hydrocarbon is a hydrogen compound with open chain structures of Carbons. This compound includes: a. Alkane: [CnH2n+2] with a single bond between the Carbon atom Ex: Pentane: C-C-C-C-C-C

b. Alkene: [CnH2n] with one double bond between the Carbon atom Ex: 2-pentene: C-C=C-C-C c. Alkyne: [CnH2n-2] with one triple bond Ex: 2-pentyne: C-CC-C-C P.S: Compound with formula [CnH2n-2] can also called Alkadienes (with two double bonds) Ex: C=C-C=C

2. Alicyclic Hydrocarbon An alicyclic hydrocarbon is a hydrogen compound with close chain structures of carbons. Ex:

3. Aromatic Hydrocarbon An aromatic hydrocarbon is a hydrogen compound with close ring structures of carbons. Ex: Benzene

As shown in benzene formula above. The ring seems to have three C-C bond and three C=C bonds. The bonds between each carbon atom are actually identical, neither true double bond nor true single bond

Based on their saturated properties, hydrocarbon compounds are grouped into: Saturated Hydrocarbon and Unsaturated Hydrocarbon compound 1. Saturated Hydrocarbons Saturated hydrocarbon compounds are hydrocarbon compounds whose all C atoms in the compounds have a single bond.

Ex: Heptane

2. Unsaturated Hydrocarbons Unsaturated hydrocarbons compounds are the hydrocarbon compounds where one or more C atoms in the compounds have double or triple bond. Ex: Pentene

Name, Isomer, and Properties of Hydrocarbon A. Alkane Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon(C) and hydrogen(H), these atoms are linked together exclusively by single bonds without any cyclic structure. Straight chain alkanes are named by counting the number of carbon atoms in the chain and adding the family suffix-ane.
General Formula: [CnH2n+2]

Molecular Formula 1 CH4 2 C2H6 3 C3H8 4 C4H10 5 C5H12 6 C6H14 7 C7H16 8 C8H18 9 C9H20 10 C10H22

Structure CH4 CH3-CH3 CH3-CH2-CH3 CH3-CH2-CH2-CH3 CH3-CH2-CH2-CH2-CH3 CH3-CH2-CH2-CH2-CH2-CH3 CH3-CH2-CH2-CH2-CH2-CH2-CH3 CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3 CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3 CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane

Branched-chain alkanes are named by following four steps: 1. Name the main chain. Find the longest continous chain of carbons present in the molecule, and use the name of that chain as the parent name. 2. Number the carbon atoms in the main chain. 3. Identify and number the branching substituent. If there are two substituent groups on the same carbon, assign the same number to both. There must always be as many number in the name as there are subtituents. 4. Write the name as a single word. If two or more identical substituents are present, use one of the prefixes di-, tri-, tetra-, and so forth, but dont use these prefixes for alphabetizing purposes. Alkane Isomer Ex: C6H14 (5 isomers) 1. 2. 3. 4. 5. Hexane 2-Methylpentane 3-Methylpentane 2,2-Dimethylbutane 2,3-Dimethylbutane CH3-CH2-CH2-CH2-CH2-CH3 CH3-CH2-CH2-CH(CH3)-CH3 CH3-CH2-CH(CH3)-CH2-CH3 CH3-CH2-C(CH3)2-CH3 CH3-CH(CH3)-CH(CH3)-CH3

Properties of Alkane Every member of alkane is differentiated based on the difference of molecular mass. The different result in the regular change. Physical Properties of Alkane The longer the carbon chain. The more higer the melting point, boiling point and the density. Between matching alkane, the alkane with branched isomer have lesser melting and boiling point. Compound Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane Molecular Formula CH4 CH3CH3 CH3CH2CH2 CH3(CH2)2CH3 CH3(CH2)3CH3 CH3(CH2)4CH3 CH3(CH2)5CH3 CH3(CH2)6CH3 CH3(CH2)7CH3 CH3(CH2)8CH3 Mr Boiling Point (C) -162 -89 -42 -1 36 69 98 126 151 174 Melting Point (C) -183 -183 -190 -138 -130 -95 -91 -57 -54 -30 Phase at Room Temperature Gas Gas Gas Gas Liquid Liquid Liquid Liquid Liquid Liquid

16 30 44 58 72 86 100 114 128 142

Liquid phase continue until the 14th carbon. The solid phase happen in the 18th carbon of alkane. All alkane cannot dissolve in water Chemical Properties of Alkane 1. Alkane can easily oxidize (Combustion) CnH2n+2 + O2 CO2 + H2O (Perfect Combustion) C + H2O or CO + H2O (Not Perfect Combustion) Ex: CnH6 + O2 2. Subtitution Reaction Ex: Subtitution by chlorine is called chlorination CH4 + Cl2 3. Cracking Reaction Ex: Cracking reaction of ethane produces ethylene or ethene and hydrogen gas used in industries CH3Cl + HCl 2CO2 + 3H2O

B. Alkene The alkenes are a group of hydrocarbon with a carbon-carbon double bond somewhere in the compounds (-C=C-) General Formula: [CnH2n] Only one double bonds allowed to use. (n=1, is not exist) Molecular Formula 2 C2H4 3 C3H6 4 C4H8 5 C5H10 6 C6H12 7 C7H14 8 C8H16 9 C9H18 10 C10H20 n Structure CH2=CH2 CH2=CH-CH3 CH2=CH-CH2-CH3 CH2=CH-CH2-CH2-CH3 CH2=CH-CH2-CH2-CH2-CH3 CH2=CH-CH2-CH2-CH2-CH2-CH3 CH2=CH-CH2-CH2-CH2-CH2-CH2-CH3 CH2=CH-CH2-CH2-CH2-CH2-CH2-CH2-CH3 CH2=CH-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3 Name Ethene Propene Butene Pentene Hexene Heptene Octene Nonene Decene

The alkenes are straight chain or branched chain compound. There is a double bond present, so they are called unsaturated compound.

Naming The Alkenes 1. Alkenes names are gotten by changing the suffix-ane in alkane compound into ene. 2. The parent chain chosen is the longest chain containing the double bond. 3. The numbering of C atom in the parent chain is not started from one of the end of the chain such that C atom with double bond has the smallest number. 4. The position of the double bond is shown by number. The number shows the double bond carbon atom on the edge, the one with small number. 5. The writing of side chain is the same with the one in alkane. Alkene Isomer
1 -hexene cis 2-hexene trans 2 -hexene cis 3-hexene trans 3-hexene 2, 3-dimethyl-2-butene 2-methyl-2-hexene 3-methyl-1-pentene

Properties of Alkene 1. Addition Ex: -Hydrogenation R-CH=CH-RI R-CH2-CH2-RI

-Chlorination R-CH=CH-RI R-CH(Cl)-CH(Cl)-RI

2. Polymerization (merging process of molecule from small to big) Ex: 2 alkene do polymerization reaction R-CH=CH-RI + R-CH=CH-RI Then itll become... ( -CH(R)-CH(RI)- + -CH(R)-CH(RI)- ) 3. Combustion (oxidation with oxygen) Just like alkane, if hydrocarbon do combustion reaction perfectly. The result will be: CO2 + H2O We can change R into H or alkyl

C. Alkyne The alkenes are a group of hydrocarbon with a carbon-carbon triple bond somewhere in the compound (-CC-) General Formula: [CnH2n-2] Only one triple bonds allowed to use. (n=1, is not exist) Molecular Formula 2 C2H2 3 C3H4 4 C4H6 5 C5H8 6 C6H10 7 C7H12 8 C8H14 9 C9H16 10 C10H18 n Structure CHCH CHC-CH3 CHC-CH2-CH3 CHC-CH2-CH2-CH3 CHC-CH2-CH2-CH2-CH3 CHC-CH2-CH2-CH2-CH2-CH3 CHC-CH2-CH2-CH2-CH2-CH2-CH3 CHC-CH2-CH2-CH2-CH2-CH2-CH2-CH3 CHC-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3 Name Ethyne Propyne Butyne Pentyne Hexyne Heptyne Octyne Nonyne Decyne

The alkynes are straight chain or branched chain compound. There is a triple bond present, so they are called unsaturated compound, like alkenes. Naming The Alkenes 1. Alkynes names are gotten by changing the suffix-ane in alkane compound into yne. 2. Always choose the longest chain containing the triple bond. 3. The numbering of C atom in the parent chain is not started from one of the end of the chain such that C atom with triple bond has the smallest number. 4. The position of the triple bond is shown by number. The number shows the triple bond carbon atom on the edge, the one with small number. 5. The writing of side chain is the same with the one in alkane or alkene. Addition of hydrogen, halogens, and related reagents Alkynes characteristically undergo reactions that show that they are "doubly unsaturated," meaning that each alkyne unit is capable of adding two equivalents of H2, halogens or related HX reagents (X = halide, pseudohalide, etc.). Depending on catalysts and conditions, alkynes add one or two equivalents of hydrogen. Hydrogenation to the alkene is usually more desirable since alkanes are less useful: RCCR' + H2 cis-RCH=CR'H The largest scale application of this technology is the conversion of acetylene to ethylene in refineries. The steam cracking of alkanes affords a few percent acetylene, which is selectively

hydrogenated in the presence of a palladium/silver catalyst. For more complex alkynes, the Lindlar catalyst is widely recommended to avoid formation of the alkane, for example in the conversion of phenylacetylene to styrene.

Uses of Hydrocarbons
Molecular Formula Molecular Mass Melting Point (oC) Boiling Point (oC) State (25oC, 101.3kPa) Density (liquid g cm-3, 20oC) Flashpoint (oC) Enthalpy of Combustion (kJ mol-1)

Name

Uses major component of natural gas (fuel) component of natural gas (fuel) component of liquefied petroleum gas (LPG), bottled gas (fuel) component of liquefied petroleum gas (LPG), cigarette lighters (fuel) component of petrol (fuel) component of petrol (fuel) component of petrol (fuel) major component of petrol (fuel) component of petrol (fuel)

methane

CH4

16

-182

-162

gas

-889

ethane

C2H6

30

-183

-88.6

gas

<-1557

propane

C3H8

44

-188

-42.1

gas

-2217

butane

C4H10

58

-138

-0.5

gas

-2874

pentane

C5H12

72

-130

36.1

liquid

0.626

-49

-3536

hexane

C6H14

86

-95.3

68.7

liquid

0.659

-22

-4190

heptane

C7H16

100

-90.6

98.4

liquid

-4

-4847

octane

C8H18

114

-56.8

126

liquid

-5506

nonane

C9H20

128

decane

C10H22

142

-30

174

liquid

0.730

component of petrol (fuel) component of diesel fuel & heating oil

hexadecane C16H34

226

18.5

288

liquid

0.775

Hydrocarbons are one of the Earth's most important energy resources. The predominant use of hydrocarbons is as a combustible fuel source. In their solid form, hydrocarbons take the form of asphalt. Mixtures of volatile hydrocarbons are now used in preference to the chlorofluorocarbons as a propellant for aerosol sprays, due to chlorofluorocarbon's impact on the ozone layer. Methane [C] and ethane [C2] are gaseous at ambient temperatures and cannot be readily liquified by pressure alone. Propane [C3] is however easily liquified, and exists in 'propane bottles' mostly as a liquid. Butane [C4] is so easily liquified that it provides a safe, volatile fuel for small pocket lighters. Pentane [C5] is a clear liquid at room temperature, commonly used in chemistry and industry as a powerful nearly odorless solvent of waxes and high molecular weight organic compounds, including greases. Hexane [C6] is also a widely used non-polar, non-aromatic solvent, as well as a significant fraction of common gasoline. The [C6] through [C10] alkanes, alkenes and isomeric cycloalkanes are the top components of gasoline, naptha, jet fuel and specialized industrial solvent mixtures. With the progressive addition of carbon units, the simple non-ring structured hydrocarbons have higher viscosities, lubricating indices, boiling points, solidification temperatures, and deeper color. At the opposite extreme from [1C] methane lie the heavy tars that remain as the lowest fraction in a crude oil refining retort. They are collected and widely utilized as roofing compounds, pavement composition, wood preservatives (the creosote series) and as extremely high viscosity sheer-resisting liquids.