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JOAZAIZULFAZLI JAMALIS
Department of Chemistry Faculty of Science Universiti Teknologi Malaysia
joazaizul@kimia.fs.utm.my
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Hydrocarbons
Aliphatic
Alkane Alkene Alkyne
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Alkanes
all bonds are single bonds (C-C and C-H, bonds) Known as saturated hydrocarbons Categorized as acyclic or cyclic General formula for acyclic alkanes: CnH2n+2 General formula for cyclic alkanes: CnH2n
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Acyclic alkanes contain only linear and branched chains of carbons atoms.
Alkanes Homolog
Number of Carbon Atoms
Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane
1 2 3 4 5 6 7 8 9 10
Cycloalkanes Homolog
Number of Carbon Atoms
3 4 5 6 7
H 1 1o H Co H o 1 o 1 2 Ho o H H 3 1 2o H C C C C Ho 1 1o H Ho Ho H o o
o
C C
H H C H H H C H H
Alkyl Groups
- removing one hydrogen atom from the alkane
- substituent groups
- The symbol is R.
Alkane
CH3-H methane CH3CH2-H ethane
Alkyl group
CH3methyl CH3CH2ethyl
Abbreviation
MeEt-
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CH3CH2CH2
CH3CH2CH3 propane
Isopropyl (remove 2 H from propane)
CH3CHCH3
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CH3CH2CH2CH2
CH3CH2CH2CH3
n-butane
CH3CH2CHCH3
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CH3 CH3CHCH3
isobutane
IUPAC NAMES
International Union of Pure and Applied Chemistry
1. Find the longest continuous chain of carbon atoms, and name it. 2. Use the chain with greater number of substituents as the main chain. 3. Substituents can be an alkyl groups, hydroxyl groups (-OH), halogen (-Cl,-Br,-I,-F), phenyl groups etc.
CH3CH2CH2CH2CHCH2CH2CH3 CH3
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CH3CH2CH2CH2CHCH2CH3 CH2CH2CH3
3 2 1
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Rule 2 & 3: Numbering the Main Chain and naming the alkyl groups
1. Number the longest chain, start with the end of the chain nearest to a substituent
2. Substituted carbons always get the lowest possible number
CH3CHCH2CH2CH3 CH3
2-methylpentane (IUPAC)
isohexane (common name) 17
3-ethyl-2,4,5-trimethylheptane
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when two or more substituents are present, list them in alphabetical order. when two or more of the same alkyl groups (or other substituent) are present, use the prefixes di-, tri-, tetra-, hexa- etc. follow the alphabet of the alkyl groups, NOT the prefixes di-, tri-, tetra- (IGNORE alphabet of the prefixes)
CH2CH3
When both directions lead to the same lowest number for one of the substituents, choose the direction that gives the lowest possible number to the remaining substituents.
[6,3,4]
[3,5,6]
If the same number is obtained in both directions, follow the alphabet of the substituent.
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Cl CH3CHCHCH3 Br
Certain common names are still used in the IUPAC system Eg.
CH3 CH3CH
Isopropyl
CH3 CH3CHCH2
Isobutyl
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Cycloalkanes
Rings of carbon atoms (CH2 groups) Formula: CnH2n Nonpolar, insoluble in water Compact shape Melting and boiling points similar to branched alkanes with same number
of carbons
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Nomenclature of Cycloalkane
no number is needed for a single substituent on a ring
H3C
Cl
methylcycloheptane
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chlorocyclohexane
CH3
methylcyclopentane May be cycloalkyl attachment to chain.
CH2CH2CH2CH2CH3
1-cyclobutylpentane 29
if more than one substituent, arrange in alphabetical order give number to the carbon of the ring choose the best combination of numbers
CH3CH2CH2 H3 C
1 4 3 2 2 3 1 4
CH2CH3
H3C
CH3 CH3
Complex Substituents
If the branch has a branch, number the carbons from the point of attachment. Name the branch off the branch using a locator number. Parentheses are used around the complex branch name.
2 3
1-methyl-3-(1,2-dimethylpropyl)cyclohexane
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Isomerism
Molecules which have the same molecular formula, but differ in the arrangement of their atoms, are called isomers.
C4H10
Structural Isomers
CH3
CH3CH2CH2CH3
and
CH3CHCH3
C2H6O
H3C O CH3 and CH3CH2OH
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CH3 H
trans 1,2-dimethylcyclopropane
CH3 CH3
cis 1,2-dimethylcyclopropane
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Source of alkanes
1. Natural gas methane (60%-80%) ethane, propane and butane 2. Petroleum gasoline kerosene diesel fuel
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CH3CH
CH3CH2OH
MW =44 BP=21oC
dipole-dipole attraction
MW = 46 BP=79oC
hydrogen bonding (strong)
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b. Boiling points(b.p) increases as the numbers of carbons increases because of increased surface area CH3CH2CH2CH3 b.p = 0oC
CH3CH2CH2CH2CH3
b.p = 36oC
CH3CH2CH2CH2CH2CH3
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b.p = 69oC
c. The b.p of isomers decrease with branching because of decreased surface area
branched alkanes are more compact, less surface contact between molecules, less van der Waals attractions.
CH3CH2CH2CH2CH3
b.p = 36C
CH3CH2CHCH3 CH3
b.p = 28C
Synthesis of Alkanes
1. Hydrogenation of Alkenes
Alkene + H2 Alkane
Catalyst required, usually Pt, Pd, or Ni.
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2.
H Cl
H H
CH3CH2CH2CH2Br
LiAlH4
CH3CH2CH2CH3
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3.
R MgX
H O H
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R H
Mg(OH)X
Reactions of Alkanes
1. Combustion
2 CH3CH2CH2CH3 + 13 O2 heat 8 CO2 + 10 H2O
3. Halogenation
CH4 + Cl2 heat or light CH3Cl + CH2Cl2 + CHCl3 +CCl4
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Mechanism of Halogenation
Step 1 (Initial Step) Homolytic cleavage of the chlorine molecule
Cl
Cl
hv or heat
2 Cl
Step 2 (Propagation Step) i) Chlorin radical attack alkane molecule to form alkyl radical
R
ii)
Cl
HCl
+ R
Cl
Cl
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Cl + Cl
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Step 3 (Termination Step) Free radicals will combine or transfer its electrons to form a molecule
R Cl R
+ +
R
Cl
R Cl R
R Cl Cl
+ Cl
Halogenation will give mixtures of products because there are more than one atom of hydrogen that will be substituted.
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CH3CH2CH3 + Cl2
heat or uv light
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