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Organic Chemistry
Two credits
Second Semester 2009
Chapter 2
Alkanes and
Cycloalkanes
IUPAC Nomenclature of
Unbranched Alkanes
IUPAC Names of Unbranched Alkanes
Retained:
methane CH4
ethane CH3CH3
propane CH3CH2CH3
butane CH3CH2CH2CH3
IUPAC Names of Unbranched Alkanes
Note:
n-prefix is not part of IUPAC name of
any alkane.
For example: n-butane is "common name"
for CH3CH2CH2CH3; butane is "IUPAC name."
Others:
CH3CH2CH2CH2CH2CH3
(CH3)2CHCH2CH2CH3
(CH3CH2)2CHCH3
(CH3)2CHCH(CH3)2
(CH3)3CCH2CH3
The C6H14 Isomers
CH3CH2CH2CH2CH2CH3
Hexane
(CH3)2CHCH2CH2CH3
2-Methylpentane
(CH3CH2)2CHCH3
3-Methylpentane
The C6H14 Isomers
(CH3)2CHCH(CH3)2
2,3-Dimethylbutane
(CH3)3CCH2CH3
2,2-Dimethylbutane
Methyl H C or CH3
H H
Ethyl H C C or CH3CH2
H H
Unbranched Alkyl Groups
R H R
If potential point of attachment is at the end
of the chain, take the IUPAC name of the
corresponding unbranched alkane and replace
the -ane ending by -yl.
Unbranched Alkyl Groups
R H R
If potential point of attachment is at the end
of the chain, take the IUPAC name of the
corresponding unbranched alkane and replace
the -ane ending by -yl.
H H H H
H C C C C or CH3CH2CH2CH2
H H H H
Butyl
Unbranched Alkyl Groups
CH3(CH2)4CH2 Hexyl
CH3(CH2)5CH2 Heptyl
H H H
H C C C or CH3CH2CH2
H H H
and
H H H
H C C C H or CH3CHCH3
H H
The C3H7 Alkyl Groups
H H H
H C C C or CH3CH2CH2
H H H
H H H
H C C C H or CH3CHCH3
H H
H H H
H C C C or CH3CH2CH2
H H H
H H H
H C C C H or CH3CHCH3
H H
CH3
3 2 1
CH3 C CH2
CH3
1 2
CH3 C CH3
Octane
Branched alkanes
4-Ethyloctane
Branched alkanes
4-Ethyl-3-methyloctane
4-Ethyl-3,5-dimethyloctane
2 4 6 8 7 5 3 1
3 5 7 6 4 2
1 8
7 5 3 1
6 4 2
8
2,2,6,6,7-Pentamethyloctane?
Cycloalkane Nomenclature
Cycloalkanes
Cycloalkanes are alkanes that contain a ring of
three or more carbons.
Count the number of carbons in the ring, and add
the prefix cyclo to the IUPAC name of the
unbranched alkane that has that number of
carbons.
Cyclopentane Cyclohexane
Cycloalkanes
Name any alkyl groups on the ring in the usual
way.
CH2CH3
Ethylcyclopentane
Cycloalkanes
Name any alkyl groups on the ring in the usual
way.
List substituents in alphabetical order and count
in the direction that gives the lowest numerical
locant at the first point of difference.
H3C CH3
CH2CH3
3-Ethyl-1,1-dimethylcyclohexane
Sources of Alkanes and Cycloalkanes
Light
Lightgasoline
gasoline
(bp:
(bp:25-95
25-95°C)
°C)
Crude oil C15 -C25
Gas
Gasoil
oil
Refinery
Refinerygas
gas (bp:
(bp: 230-340
230-340°C)
°C)
C1-C4 Residue
Residue
Just for general knowledge, will not be tested on
Petroleum Refining
Cracking
converts high molecular weight hydrocarbons
to more useful, low molecular weight ones
Reforming
increases branching of hydrocarbon chains
branched hydrocarbons have better burning
characteristics for automobile engines
Physical Properties of Alkanes
and Cycloalkanes
Boiling Points of Alkanes
+ +–
––
+ +–
––
+ – +–
+ – + –
+ – + –
– + – +
Octane: bp 125°C
2-Methylheptane: bp 118°C
2,2,3,3-Tetramethylbutane: bp 107°C
Chemical Properties:
Combustion of Alkanes
5471 kJ/mol
5 kJ/mol
5466 kJ/mol
8 kJ/mol
5458 kJ/mol
6 kJ/mol
5452 kJ/mol
5471 kJ/mol
25 5466 kJ/mol
+ O2
2 5458 kJ/mol
5452 kJ/mol
25
+ O2 25
2 + O2 25
2 + O2
2
8CO2 + 9H2O