Organic Chemistry

Chapter 24 Part 1
Hydrocarbons

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Common Elements in Organic Compounds

24.1
Classification of Organic
Compounds
Classification of Hydrocarbons

24.1
 Bonding Patterns of Carbon
• Saturated C – attached to four atoms or
groups
• Unsaturated C – has double or triple bond
 Alkanes

Alkanes have the general formula CnH2n+2where n = 1,2,3,…

• only single covalent bonds
• saturated hydrocarbons because they contain the
maximum number of hydrogen atoms that can bond with the
number of carbon atoms in the molecule

CH4 C2H6 C3H8

methane ethane propane

24.2
Alkane Nomenclature

24.2
Structural isomers are molecules that have the same
molecular formula but different structures
24.2
 Isomers

Copyright 2012 John Klein, Organic Chemistry 1e 2-9

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 Isomerism
• Isomers – compounds displaying the phenomenon
• Structural or constitutional – same MF but different
arrangement of atoms in the molecule
– Chain, position and functional

• Stereoisomerism – same bonding arrangement of atoms

but differ in the manner they are arranged in a three-
dimensional space
– Cis and trans (geometric) and optical isomers

Copyright 2012 John Klein, Organic Chemistry 1e 2 -10

Wiley & Sons, Inc.
 How many structural isomers does pentane, C5H12, have?

H H H H H

H C C C C C H

H H H H H
H CH3 H
n-pentane
H C C C H
H CH3 H H H CH3 H
H C C C C H
2,2-dimethylpropane
H H H H
2-methylbutane
24.2
 Alkyl Groups
• An alkyl group is obtained from an alkane by removing
one H
• Name is derived from alkane by changing ane to yl.
 Alkane Nomenclature

1. The parent name of the hydrocarbon is that given to the

longest continuous chain of carbon atoms in the molecule.
CH3

CH3 CH2 CH2 CH CH2 CH2 CH3 4-methylheptane

1 2 3 4 5 6 7

2. An alkane less one hydrogen

atom is an alkyl group.

CH4 methane

CH3 methyl
24.2
 Alkane Nomenclature

3. When one or more hydrogen atoms are replaced by other

groups, the name of the compound must indicate the
locations of carbon atoms where replacements are made.
Number in the direction that gives the smaller numbers for
the locations of the branches.
CH3

CH3 CH CH2 CH2 CH3

1 2 3 4 5
2-methylpentane CH3

CH3 CH2 CH2 CH CH3

1 2 3 4 5

4-methylpentane
24.2
 Alkane Nomenclature

4. Use prefixes di-, tri-, tetra-, when there is more than one
alkyl branch of the same kind.
CH3 CH3

CH3 CH CH CH2 CH2 CH3

1 2 3 4 5 6

2,3-dimethylhexane
CH3

CH3 CH C CH2 CH2 CH3

1 2 3 4 5 6
CH3

3,3-dimethylhexane
24.2
 Alkane Nomenclature

5. Use previous rules for other types of substituents.

Br NO2

CH3 CH CH CH3
1 2 3 4
2-bromo-3-nitrobutane

Br NO2

CH2 CH2 CH CH3

1 2 3 4

1-bromo-3-nitrobutane

24.2
What is the IUPAC name of the following compound?
CH3 CH2CH3

CH3 CH CH2 CH CH2 CH2 CH2 CH3

1 2 3 4 5 6 7 8

4-ethyl-2-methyloctane

What is the structure of 2,4-dimethylhexane?

CH3 CH3

CH3 CH CH2 CH CH2 CH3

1 2 3 4 5 6

24.2
 Alkane Reactions
Combustion
CH4 (g) + 2O2 (g) CO2 (g) + 2H2O (l) H0 = -890.4 kJ
Photochemical Halogenation – a substitution reaction
light
CH4 (g) + Cl2 (g) CH3Cl (g) + HCl (g)

Cl2 + energy Cl• + Cl•

H H

Cl• + H C H •C H + HCl

H H
H H

H C• + Cl Cl H C Cl + Cl•

H H 24.2
24.2
 Cycloalkanes

Alkanes whose carbon atoms are joined in rings are called

cycloalkanes. They have the general formula CnH2n where n =
3,4,…

24.2
 Alkenes

Alkenes have the general formula CnH2n where n = 2,3,…

• contain at least one carbon-carbon double bond
• also called olefins

Ethene or ethylene Propene or propylene

CH2=CH2 CH3CH=CH2
24.2
Ethylene is a gas and is known as the “fruit-ripening
hormone.” Every fruit has a certain level of ethylene
production throughout its lifecycle. However, in some fruits,
ethylene levels shoot up when the fruit starts ripening.
 Naming of alkenes
• Select the longest chain passing through the = as the parent
alkene.
• If necessary (starting with 4 Cs) number the chain from the end
nearer the = bond.
• Locate the first carbon with the double bond then the name of
the parent with ending ene.
 Alkenes

 Position Isomerism in Alkenes

CH2 CH CH2 CH3 CH3 CH CH CH3
1-butene 2-butene
1-butene and 2-butene are position isomers they differ
only on the location of the double bond
Cis-dichloroethylene and trans dichloroethylene are
geometric isomers.

Cl Cl Cl H
C C C C
H H H Cl
cis-dichloroethylene trans-dichloroethylene

24.2
 Geometric Isomers
Cis and trans isomers – differ in how the atoms are arranged in reference
to the plane of the double bond

Cis – when identical groups are on the same side of the double bond

Trans – when identical groups are on opposite sides of the double bond

Copyright 2012 John Klein, Organic Chemistry 1e 2-27

Wiley & Sons, Inc.
Cis-Trans Isomerization in the Vision Process

24.2
 Alkene Reactions
Preparation by Cracking
Pt
C2H6 (g) catalyst
CH2 CH2 (g) + H2 (g)

Addition Reactions
CH2 CH2 (g) + HBr (g) CH3 CH2Br (g)

CH2 CH2 (g) + Br2 (g) CH2Br CH2Br (g)

24.2
 Alkynes

Alkynes have the general formula CnH2n-2 where n = 2,3,4,…

• contain at least one carbon-carbon triple bond

CH C CH2 CH3 CH3 C C CH3

1-butyne 2-butyne
1-butyne and 2-butyne are position isomers

Production of acetylene or Ethyne

CaC2 (s) + 2H2O (l) C2H2 (g) + Ca(OH)2 (aq)

Acetylene, HC  CH can be prepared by adding water to

calcium carbide, CaC2.

24.2
 Naming of alkynes
• Same as alkynes except that the ending is
yne.
• Starting with 4 carbons indicate the location
of the triple bond (position isomers)
• There is only one propyne but there are two
butynes (1-butyne and 2- butyne)
 Alkyne Reactions

Hydrogenation
CH CH (g) + H2 (g) CH2 CH2 (g)

Addition Reactions
CH CH (g) + HBr (g) CH2 CHBr (g)
CH CH (g) + Br2 (g) CHBr CHBr (g)
CH CH (g) + 2Br2 (g) CHBr2 CHBr2 (g)

24.2
 Aromatic Hydrocarbons
H H

H C H H C H
C C C C

C C C C
H C H H C H

H Benzene H

24.3
 Aromatic Compound Nomenclature

ethylbenzene aminobenzene
CH2CH3 Cl NH2 NO2

chlorobenzene nitrobenzene

Br Br
1
6 2 Br

5 3 Br
4
1,2-dibromobenzene 1,3-dibromobenzene
24.3
 Aromatic Hydrocarbons

Copyright 2012 John Klein, Organic Chemistry 1e 2 -35

Wiley & Sons, Inc.
 Natural Gas and Petroleum
• Natural Gas:
– 50 - 90% Methane
– 1 - 10% Ethane
– Up to 8% Higher Alkanes (mostly Propane and
Butanes)
• Petroleum (crude oil):
– Complex mixture of acyclic and cyclic hydrocarbons

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 Petroleum Refining
• Refining: Isolation of
soil, sand, sulfur, etc.,
from the crude oil and
physical separation of
the hydrocarbons
mixture into several
fractions.
• Fractional Distillation:
Process of separating
different components
from a mixture based
on their boiling points.
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Chemistry In Action: The Petroleum Industry

Crude Oil