Chapter2 Alkanes
Chapter2 Alkanes
Chapter2 Alkanes
CHM 207
CHAPTER 2:
ALKANES
Structure
Reactions:
SUBTOPICS Free radical substitution
Combustion
Nomenclature of straight HC
No of C atom, n Name No of C atom, n Name
1 Methane 6 Hexane
2 Ethane 7 Heptane
3 Propane 8 Octane
4 Butane 9 Nonane
5 Pentane 10 Decane
Alkyl Group
• If a hydrogen is removed from an alkane, the structure
obtain is called an alkyl group. This group is named by
replacing the end –ane of the parent with –yl, eg:
– Removing a hydrogen atom in methane, CH4, gives a methyl
group, CH3-
– Removing a hydrogen atom in ethane, CH3CH3, gives an ethyl
group, CH3CH2-
1 2 3 4 5 6 1 2 3
CH3 CH2 CH CH2 CH2 CH3 CH3 CH2 CH CH2 CH2 CH3
CH3
CH3
CH CH2 CH3
CH CH2 CH3
CH3 CH CH3
CH3 CH CH3
CH2
CH2
CH3
CH3
correct wrong
A hexane with 2 substituents A hexane with 1 substituent
Step 2: Number the atoms in the main chain
a) Beginning at the end nearer the first branch point
(smallest number)
8 7 6 5 4 3 2 1 1 2 3 4 5 6 7 8
correct wrong
isopropyl group
1CH3
7 CH3
CH2 CH3
2
6 CH2 CH3
CH CH2 5CH
4 CH2
CH3 3 CH
CH3
4 CH
5 CH2 6
CH2
3 CH2 2
CH2
correct 7 CH3
wrong
1 CH3
b) If branching occurs at equal distance from both ends, begin
numbering at the end nearer the second branch point
8CH3 1CH3
CH2 CH3 2CH2 CH3
7
2 7
CH3 CH CH CH2 CH3 CH CH CH2 8
6 4 3 1 3 5 6
CH2 CH2 CH CH3 CH2 CH2 CH CH3
5 4
CH2 CH2
CH3 CH3
correct wrong
Step 3: Identify and number the substituents
a) Give each substituent a number that corresponds to
its position on the parent chain
8
9 CH2
CH3 CH2 CH3
7 parent: nonane
2
CH3 CH CH CH2 Substituents:
6 4 3 1
CH2 CH2 CH CH3 C3 CH2CH3 3-ethyl
5 C4 CH3 4-methyl
CH2 C6 CH2CH3 6-ethyl
CH3
b) Two substituents on the same carbon gets the same
number
CH3
CH2 CH3 parent: hexane
Substituents:
CH3 C CH C2 CH3 2-methyl
CH2 CH2 CH3 C4 CH3 4-methyl
CH3 C4 CH2CH3 4-ethyl
4-ethyl-3-methylheptane
H3C 8CH3
CH2 CH3 CH2 CH3
7
2
CH3 C CH CH3 CH CH CH2
4 3 2 1 6 4 3 1
6 CH2 CH2 CH CH3
CH2 CH2 CH3
5 5
CH3
4-ethyl-2,4-dimethyl hexane CH2
CH3
3,6-diethyl-4-methyloctane
• Alkanes can have many different types of
substituents.
For example:
NO2 Br
1 2 3 4 5
CH3 CH CH CH3 CH3
3-bromo-2-nitropentane
Exercises:
CH CH2 CH
CH3 CH2 CH2 CH3
alicyclic compounds
A hydrocarbon that contains C atoms joined to form a ring.
Cycloalkanes – all carbons of the ring are saturated
ethylcyclopentane 1-cyclopropylbutane
Step 2: Number the substituent and write the name
a) Start at a point of attachment and number the
substituents so that the second substituent has the
lowest possible number
b) If necessary, proceed to the next substituent until a
point of difference is found
1 1
2 2 6
6
3 5
5 3
4 4
1,5-dimethylcyclohexane
1,3-dimethylcyclohexane
correct wrong
lower higher
• When the acyclic portion of the molecule contains more
carbon atoms than the cyclic portion (or when it contains
an important fuctional group), the cyclic portion is named
as a cycloalkyl substituent.
Example:
4-cyclopropyl-3-methyloctane 5-cyclobutyl-1-pentyne
ISOMERISATION
Structural isomers:
- Molecules that have the same molecular formula, but
different structure
Insoluble in water:
- alkanes are non-polar and do not form hydrogen
bonds with water molecules.
- described as ‘hydrophobic’ (water hating).
2) Densities:
water
BOILING POINTS AND MELTING POINTS OF
ALKANES
BOILING POINTS OF ALKANES
Effect of relative molecular mass on boiling point.
- the first four chain alkanes are gases.
- alkanes from C5H12 to C18H38 are liquids at room
temperature because their melting point are lower
than 28oC (301K).
- alkanes above C18H38 are solids at room
temperature.
- the boiling points of straight chain alkanes increase
steadily with relative molecular mass (due to
increasing forces of attraction between molecules).
* A larger molecule, with greater surface area and
greater van der Waals attractions, boils at higher
temperature *
Boiling points of the straight chain of
alkanes
Effect of branching on boiling point.
COMBUSTION HALOGENATION
(WITH OXYGEN) (FREE RADICAL
REACTIONS)
REACTIONS OF ALKANES
i. COMBUSTION
- Alkanes burn in a plentiful supply of air or oxygen to
produce water and CO2 only.
- for example:
C3H8 + 5 O2 → 3CO2 + 4H2O
- In a limited supply of air, combustion of alkanes
produces carbon monoxide and water
* Condition of reaction:
light or heat (high temperature) or ultraviolet radiation
(provides energy that is absorbed by reactant molecules
to produce free radicals).
MECHANISM OF FREE RADICAL
SUBSTITUTION REACTIONS
3 STEPS
hv
Cl Cl Cl Cl
chlorine atoms
ΔH = +242 kJMol-1 (free radicals)
hv = radiation energy
= movement of single electron (radical)
2) PROPAGATION STEPS
- Free radical species produce another free
radical species.
H
Cl H C H HCl + CH3
H methyl radical
methane
Cl Cl Cl2
CH3 Cl CH3Cl
CH3 CH3 H3C CH3
(by product)
FREE RADICAL SUBSTITUTION REACTIONS OF ETHANE
hv
Br Br Br Br initiation step
Br Br Br2
CH3CH2 Br CH3CH2Br termination step
f) Asphalt
- black, tarry residue remaining after removal of the other
volatile fractions
- C35 and above
Fractional distillation
ii. Cracking and Reforming Process
a) Cracking:
A process whereby a saturated hydrocarbon is
converted into an unsaturated hydrocarbon and
hydrogen.
Ethane is cracked by heating in furnace at 800 to 900 oC.
800-900oC
CH3CH3 thermal cracking H2C CH2 H2
ethane ethene
b) Catalytic reforming:
- A process for increasing the octane number of
naphthas.
catalyst catalyst
CH3CH2CH2CH2CH2CH3 -H2 -H2
* Fuel that have high octane number, has very good antiknock
properties (the fuel /air mixture burns smoothly in the combustion
chamber).
* If other fuel has octane number 90, means that the knock
properties of the fuel is same as those mixture of 10% heptane and
90% isooctane.