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C
H
CCl4
1
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Hydrocarbons
(Containing only C and H)
Aliphatic
Aromatic
Alkanes
Alkenes
Alkynes
Cycloalkanes
and
Cycloalkenes
H
H
H
H
H
H
H
H
H H
H H H
H C H
H C C H
H C C C H
H H
H H H
Condensed structural formulas (CSFs) are written by giving the name and number of atoms bonded to a particular carbon
right in front of every carbon.
CH4
CH3CH3
CH3CH2CH3
CH3 CH3
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Line-Bond Formulas
The ends and bends are carbons.
We assume every carbon is bonded to as many hydrogen atoms as needed in order to give them four bonds. (Hydrogen atoms
are never shown!)
CH3CH2CH2CH2CH2CH3
Again, all these structures represent the same compound, make no mistake! They are not isomers!
How can you tell when two or more structures are isomers (different compounds) or conformers (same compound)?
Naming is the key!
Prefix
Where are susbtituents
located?
Parent
Suffix
How many
carbons?
Named by counting the number of C atoms and adding the family suffix -ane.
The first four members have common names.
The family of alkanes forms what we call a homologous series; that is, all the members of the family form a sequence in which
there is a regular difference in the molar mass. The equation that describes the homologous series of the alkanes family is:
CnH2n + 2
(Where n is the number of C atoms.)
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Here is the list of the first twenty members of the alkanes family. Memorize the names for the first ten.
# of C atoms
Formula
Name
1
CH4
Methane
2
CH3CH3
Ethane
3
CH3CH2CH3
Propane
4
CH3CH2CH2CH3
n-Butane
5
CH3CH2CH2CH2CH3
n-Pentane
6
CH3CH2CH2CH2CH2CH3
n-Hexane
7
CH3CH2CH2CH2CH2CH2CH3
n-Heptane
8
CH3CH2CH2CH2CH2CH2CH2CH3
n-Octane
9
CH3CH2CH2CH2CH2CH2CH2CH2CH3
n-Nonane
10
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Decane
11
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Undecane
12
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Dodecane
13
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Tridecane
14
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Tetradecane
15
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Pentadecane
16
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Hexadecane
17
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Heptadecane
18
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Octadecane
19
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Nonadecane
20
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
n-Eicosane
(The n as a prefix to the name stands for normal. It means we are talking about the straight chain alkane no branches.)
Substitution patterns
Carbons can be:
The R represents more Cs.
Primary
Secondary
Tertiary
Quaternary
or
CH3
CH3
ethyl
or
CH2
CH3
CH3
CH2
CH2
or
propyl
CH3
or
CH
Isopropyl
CH3
or
Butyl
CH3
CH
CH2
Isobutyl
or
CH3
CH3
or
CH3
CH2
CH
CH3
sec-butyl
(secondary butyl)
or
tert-butyl or t-butyl
(tertiary butyl)
CH3
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Branched-chain alkanes
Can be named by following four steps:
STEP 1: Name the main chain. Find the longest continuous chain of carbons.
(You have to be careful here, remember free rotation? Make sure you get the longest chain possible.)
The longest continuous chain has five carbons, not four (the straight chain)!
STEP 2: Number the carbon atoms in the main chain. Begin at the end nearer the first branch point:
We want to give the lowest possible numbers to the branches.
STEP 3: Identify the branching substituents, and number each according to its point of attachment to the main chain:
A methyl is attached to C2.
3-ethyl-3-methylhexane
3,3-dimethylhexane
CH3CH2CHCHCH3
5
4
3 2 1
3-chloro-2-methylpentane
5
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What if?
1. Two different substituents are found at the same distance from both ends?
methyl
ethyl
1
2
What if?
2. In the same molecule theres more than one possible option for the longest chain?
CH 3
CH 3
CH2
CH 3
CH2
CH
CH
CH 2
CH2
CH
CH 2
CH
CH3
CH3
CH
CH 3
CH 3
Remember
In the name there must be as many numbers as substituents in the molecule.
F
F
CH 2
CH 3
CH 3
CH 3
CH 3
CH 2
CH 3
CH 3
CH 3
CH 2
CH 2
CH 3
CH
CH 2
CH 3
CH 2
CH 2
CH 3
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Properties of Alkanes
At room T (n-alkanes):
First four are gases.
With 5-15 Cs are liquids.
>16Cs are waxy solids.
Properties of Alkanes
The boiling and melting points for the straight-chain alkanes increase with molecular size. WHY?
Boiling Points of Alkanes
Are among the lowest of organic compounds(Why?).
CO2 + H2O
5 CO2 + H2O
5 CO2 + 6 H2O
5 CO2 + 6 H2O balanced
CH3Cl + HCl
chloromethane
Cl2
CH2Cl2 + HCl
dichloromethane
Cl2
CHCl3 + HCl
trichloromethane (chloroform)
Cl2
CHCl4 + HCl
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12.9 Cycloalkanes
Cycloalkanes
Are cyclic alkanes.
Have 2H fewer than the open chain.
Are named by using the prefix cyclo- before the name of the alkane chain with the same number of carbon atoms.
H2
C
H2
C
H2C
CH2
H2C
CH2
CH2
H2C
H2C
CH2
H2C
Cyclopropane
Cyclobutane
(mp -128 C, bp -33 C) (mp -50oC, bp -12oC)
o
H2C
CH2
H2C
CH2
CH2
C
H2
CH2
Cyclopentane
(all bond angles
are near 109o)
Cyclohexane
(all bond angles
are near 109.5o)
Cyclohexane
Cycloheptane
Cyclooctane
Naming Cycloalkanes
STEP 1: Use the cycloalkane name as the parent. That is, compounds are named as alkyl-substituted cycloalkanes
rather than as cycloalkyl-substituted alkanes. If there is only one substituent on the ring, it is not even necessary to
assign a number because all ring positions are identical.
CH3
methylcyclohexane
STEP 2: Identify and number the substituents. Start numbering at the group that has alphabetical priority, and
proceed around the ring in the direction that gives the second substituent the lower possible number.
CH3
2
3
CH2CH3
1-ethyl-3-methylcyclohexane
6
5
8
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