Documenti di Didattica
Documenti di Professioni
Documenti di Cultura
ORGANIC CHEMISTRY
CHAPTER 2
ALKANES
TOPIC
• Nomenclature
1
• Physical properties
2
• Reactions of alkanes
4
H H
H C C H H C C H
alkenes alkynes
H H
H C C H
H H benzene
ALKANES
General formula:
CnH2n+2, where n = 1, 2, ….
n = number of carbon atoms
Only single covalent bonds
saturated hydrocarbons
propane
sp3-hydridized
ethane
methane
1. NOMENCLATURE OF ORGANIC
COMPOUNDS
IUPAC (International Union of Pure and Applied Chemistry)
Compounds are given systematic names by a process that
uses:
RULE 1
Identify the longest carbon chain (not necessary straight) and write parent
name of the compound.
CH3-CH-CH2-CH3 CH3-CH-CH2-CH2-CH3
CH3 CH2-CH3
4 Carbon 6 Carbon
When a compound has two possible longest carbon chains,
select the chain/parent with more substituents.
1
CH3-CH-CH3
2 3 4 5 6 7
WRONG
CH3-CH2-CH-CH2-CH2-CH2-CH3
2 1
CH3-CH-CH3
3 4 5 6 7 CORRECT
CH3-CH2-CH-CH2-CH2-CH2-CH3
3-ethyl-2-methylheptane
RULE 2: NUMBERING THE MAIN CHAIN
(INCORRECT) (CORRECT)
2-chloro-4,6-dimethylheptane
NO2 Br
1 2 3 4 5
CH3 CH CH CH3 CH3
3-bromo-2-nitropentane
RULE 4: ORGANIZING MULTIPLE GROUPS
When two or more of the same substituent are present, use the
prefixes di-, tri-, tetra-, etc.
di- means 2 penta- means 5
tri- means 3 hexa- means 6
tetra- means 4
When substituents are alphabetized, iso-, neo-, cyclo- are not
ignored. iso- is used as part of the alkyl group name, Isobutyl is
alphabetized with i,.
hyphenated prefixes are ignored, n-butyl, t-butyl and sec-butyl
are alphabetized with b.
The number prefixes di-, tri-, tetra-, etc are ignored in
alphabetizing.
Example 1
This chain has 6 carbon atoms.
1 2 3 4 5 6
1 2 3
1 2 3 4 5 6
CH3 CH2 CH CH2 CH2 CH3
CH3 branch
methyl
ethyl
3-ethyl-4-methyloctane
Example 3
CH3 CH3
2 1
CH3CHCH2CHCHCH3
6 5 4 3
CH3
2,3,5-trimethylhexane
NOMENCLATURE CYCLOALKANES
Add cyclo- to the name of the corresponding open-chain
alkane and name each substituent on the ring.
Isopropylcyclopentane √
1-isopropylcyclopentane X
If there are two substituent , number in a way that yields the
smallest numbers possible in the finished name. If there are
identical sets of numbers, use alphabetical priority.
1, 2, 4 1, 3, 6 1, 3, 4
3 1
4 4 2 6 2
5 3 1
5 5
6
1 2 6 4 3
3. 4.
Q3 Give the systematic IUPAC names for the
cycloalkanes with the following formula:
6. 7.
8.
Q3 Give the systematic IUPAC names for the
cycloalkanes with the following formula:
5. 6.
1,1,2-trimethylcyclohexane 1-bromo-2-methylcyclohexane
7.
1-chloro-2-ethyl-4-methylcyclohexane
2. PHYSICAL PROPERTIES OF
ALKANES
water
BOILING POINTS AND MELTING POINTS
Surface area , Van der Waals’ force , boiling points , melting point
• linear VS. branched higher melting/boiling points better stacking (Van der
Waals’ force) and surface area contact.
• HIGHLY branched VS. branched more sphere-like lower surface area lower
boiling point.
REACTIVITY
Very unreactive. WHY?
Combustion
Halogenation
COMBUSTION REACTION
C2H6 + 3 O2 → 2C + 3H2O
2
HALOGENATION OF ALKANES (free radical substitution)
Alkanes react with molecular halogens (typically Cl2 and Br2) to
form halogenated alkanes (hydrocarbon that contains at least one
halogen atom). Alkanes do not react with chlorine or bromine in
the dark.
If the mixture of alkanes and chlorine or bromine is heated at high
temperature (300-400 oC), or irradiated by ultraviolet light
(provides energy that is absorbed by reactant molecules to
produce free radicals), the hydrogen atoms in the alkanes can be
replaced by chlorine or bromine atoms to produce a mixture of
products.
The reactivity of the halogens decreases in the following order :
3 STEPS
1. Chain initiation
.
homolytic cleavage of chlorine
molecules by heat or light into
two chlorine radicals hv
Cl Cl Cl Cl
chlorine atoms
(free radicals)
2. Chain propagation
hv
Br Br Br Br initiation step
Br Br Br2
CH3CH2 Br CH3CH2Br termination step
stability increases
The major product of halogenation of alkanes is the most
stable product which are:
Three major sources of alkanes from fossil fuels which are natural
gas, petroleum and coal.
Natural Gas
Composition: hydrocarbon gas mixture of relatively low boiling
alkanes (methane, butane, propane, butane and 2-methylpropane)
(C4 and below).
Used:
as a fuel to heat buildings and generate electricity
starting material for the production of fertilizers.
Petroleum
Cracking of Petroleum
A process whereby a saturated hydrocarbon is converted into an
unsaturated hydrocarbon and hydrogen.
process of breaking down of large alkane molecules (from crude
oil) into lighter fractions of smaller molecules in the absence of air.
e.g. C11H24 C9H20 + CH2 = CH2
C14H30 C8H18 + 2CH2 = CH2 + 2C + 2H2
The products are used in petrol and as feedstock for producing a wide
range of organic compounds
Example:
-Alkanes are converted to cycloalkanes and cycloalkanes are
converted to arenes in the presence of heat, pressure and
bimetallic catalyst (platinum and rhenium or platinum and
iridium).
catalyst catalyst
CH3CH2CH2CH2CH2CH3 -H2
-H2
hexane cyclohexane benzene
Asphalt/bitumen
-black residue remaining after
removal of the other volatile
fractions
- C35 and above
Boiling Number of carbon
Fraction point range atoms that the Major uses
(°C) molecules contain
As gaseous fuel, raw materials for
Fuel gas < 40 1–4
manufacture of chemicals
Petrol Fuel for motor vehicles
40 – 150 5 – 10
Naphtha Fuel for manufacture of town gas
Fuel for aeroplanes, domestic
Kerosene 150 – 220 10 – 14
liquid fuel
Fuel for trucks, lorries and
Gas oil 220 – 350 14 – 25
locomotives
Fuel for cargo ships and to
Fuel oil > 350 > 25 generate electricity in power
stations
Lubricating Lubricating oil for moving parts
> 350 > 25
oil of machinery
Bitumen > 350 > 25 For surfacing roads and roofs
THANK YOU