Chapter:
HYDROCARBONS
ALKANES
Hydrocarbon
are compounds which contain only CARBON
and HYDROGEN atoms.
– Saturated hydrocarbons
- compound with C-C
- Example : alkanes and cycloalkanes
- contain the maximum number of hydrogen atoms that
the carbon compound can possess.
Unsaturated hydrocarbons
- compounds with multiple bonds
- Example : alkenes, cycloalkenes, alkynes and
aromatic hydrocarbons
– they posses fewer than the maximum number of
hydrogen atoms.
– Each carbon atom in ALKANE is
- sp3 hybridised
- tetrahedral with four sigma bond
- all bond angles are close to 109.5o
– Alkanes IUPAC names have the –ane suffix
– The general formula : CnH2n+2
Molecular Structural formula No .of C Name
formula atoms
CH4 CH4 1 Methane
C2H6 CH3—CH3 2 Ethane
C3H8 CH3—CH2—CH3 3 Propane
C4H10 CH3—(CH2)2—CH3 4 Butane
C5H12 CH3—(CH2)3—CH3 5 Pentane
C6H14 CH3—(CH2)4—CH3 6 Hexane
C7H16 CH3—(CH2)5—CH3 7 Heptane
C8H18 CH3—(CH2)6—CH3 8 Octane
C9H20 CH3—(CH2)7—CH3 9 Nonane
C10H22 CH3—(CH2)8—CH3 10 Decane
Starting from C4H10 onwards, the alkanes show
the phenomenon of chain isomerism.
They can exist as linear or branched alkanes.
C5H12
IUPAC NOMENCLATURE
International Union of Pure and Applied
Chemistry
Branched hydrocarbon
- chain alkanes are named according to the following rules:
1. Choose the longest continuous chain of carbon atoms;
this chain determines the parent name for alkanes.
Parent name: hexane
CH3CH2CH2CH2CHCH3
|
CH3
CH3CH2CH2CH2CHCH3
CH2
CH3
Parent name : heptane
Number the longest chain beginning with the end of the
chain nearer the substituent.
6 5 4 3 2 1
CH3CH2CH2CH2CHCH3
CH3 substituent
7 6 5 4 3
CH3CH2CH2CH2CH CH substituent
3
|
2CH2
|
1CH3
- Use rule number 2 to locate the position of the substituent.
- The position and the name of the substituent must be
written in front of the parent chain.
6 5 4 3 2 1
CH3CH2CH2CH2CHCH3
Substituent
CH3 -methyl at C-2
2-methylhexane
Substituent
7 6 5 4 3 -methyl at C-3
CH3CH2CH2CH2CH CH3
|
2 CH
2
|
1 CH
3
3-methylheptane
Some Common Substituent Groups
alkane name substituent
methane methyl CH3
ethane ethyl CH2CH3
propane propyl CH2CH2CH3
CHCH3
isopropyl
CH3
butane butyl CH2CH2CH2CH3
isobutyl CH2CHCH3
CH3
sec-butyl CHCH2CH3
CH3
tert-butyl CH3
CCH3
CH3
neopentyl CH3
CH2CCH3
CH3
cyclopropyl
cyclobutyl
phenyl C6H5
CH2C6H5 CH
benzyl 2
name substituent
Bromo -Br
Chloro -Cl
Flouro -F
Iodo -I
Hydroxyl -OH
Amino -NH2
Cyano -CN
Nitro -NO2
If two or more substituents are present, give each
substituent a number corresponding to its location on the
longest chain.
– the substituent should be listed alphabetically.
– In alphabetizing, the prefixes di, tri, tetra, sec-, tert- are
ignored except iso and neo.
1 2 3 4 5 6
CH3CHCH2CHCH2CH3
| |
CH3 CH2
|
CH3
4-ethyl-2-methylhexane
If two substituents are present on the same carbon
atom, use that number twice
CH3
|3 4 5 6
CH3CH2CCH2CH2CH3
|
2
CH2
|
1
CH3
3-ethyl-3-methylhexane
If two or more identical substituents are present, use
prefixes di-(2 identical substituents), tri-(3 identical
substituents), tetra-(4 identical substituents).
Commas are used to separate numbers from each
other.
CH3CH―CH CH3 2,3-dimethylbutane
| |
CH3 CH3
If there are two chains of equal length as the
parent chain, choose the chain with the
greater number of substituents.
7 6 5 4 3 2 1
4 3 2 1
CH3CH2-CH CH CH CHCH3
| | | |
CH3 5 CH2 CH3 CH3
|
6
CH2
7
|
CH3
2,3,5-trimethyl-4-propylheptane
Which (four substituents)
one is
correct ?
4-sec-butyl-2,3-dimethylheptane
(three substituents)
If branching occurs at an equal distance from either end
of the longest chain, choose the name that gives the lower
number at the first point of difference.
6 5 4 3 2 1
CH3CHCH2CH CHCH3
1 2 3 4 5 6
| | |
CH3 CH3 CH3
2,3,5-trimethylhexane
(NOT 2,4,5-trimethylhexane)
EXERCISE :
1. CH₃CH₂CH(CH₃)₂
2. CH₃C(CH2CH3)2(CH₂)₆CH₃
3. (CH₃)₃CCH2CH3
4. CH₃ - CH – CH₂ - CH – CH₃
CH₃ CH₂CH₃
CYCLOALKANES
- Cycloalkanes – alkanes which carbon atoms are
joined in rings.
- Cycloalkanes are known as saturated
hydrocarbon, because it has the maximum
number of bonded hydrogen (only has single
bonds).
- General formula:
CnH2n where n = 3, 4, 5, ……
NOMENCLATURE OF
CYCLOALKANES
Cycloalkanes with only one ring are named with the
prefix cyclo- to the names of the alkanes (contain the
same number of carbon atoms).
C3H6 cyclopropane
C4H8 cyclobutane
C5H10 cyclopentane
If only one substituent is present, it is not necessary to
designate its position.
chlorocyclopropane
Cl
CH3 methylcyclohexane
– if two substituents are present, number carbon in the
ring beginning with the substituent according to the
alphabetical order
– number in the direction that gives the next substituent
the lowest number possible.
CH3
3
2
4 CH2CH3
1
5 6
1-ethyl-2-methylcyclohexane
NOT
1-ethyl-6-methylcyclohexane
2
Cl 3 1
Cl
4 5
1,3-dichlorocyclopentane
(NOT 1,4-
dichlorocyclopentane)
When three or more substituents are present, begin at
the carbon with substituent that leads to the lowest set
of locants.
CH2CH3 1
2 3
3 2 3
1 4
Cl 4 1 CH3
5 6 4
6 5
1-chloro-3-ethyl-4-
methylcyclohexane
4- chloro-2-ethyl-1-
methylcyclohexane
H3C CH2CH3
CH3
1-ethyl-1,3-dimethylcyclopentane
(NOT 3-ethyl-1,3-dimethylcyclopentane)
CH2CH2CH2CH2CH3
1-cyclobutylpentane
