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Hydrocarbons
Organic
chemistry is
important in
nanotechnology.
A carbon
nanotube forest
is shown here.
General, Organic, and Biochemistry, 10e
John Wiley & Sons, Inc
Hein and Pattison
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3
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4
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5
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Your Turn!
H H
1
C C H
H C H
2
H C
H H
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Your Turn!
120o
H H
1
C C H
H C H
2
H C 109.5o
H H
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For example,
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Figure 19.3 Types of formulas and models used to represent
organic molecules. Each diagram is a representation of a
propane molecule.
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Lewis structure Shows all bonds, all atoms, and all nonbonding
electrons
Structural formula Same as Lewis structure except nonbonding
electrons are not shown
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15
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Hydrocarbons
Hydrocarbons are organic compounds that contain only
carbon and hydrogen atoms. (e.g. propane, CH3CH2CH3
is a hydrocarbon but ethanol, CH3CH2OH is not).
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Hydrocarbons
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Your Turn!
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Your Turn!
CnH2n+2 = C9H20
CH3CH2CH2CH2CH2CH2CH2CH2CH3
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Isomerism
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Isomerism
Carbon can form four single bonds each, nitrogen can form
three single bonds, oxygen can only form two single
bonds, and hydrogen and the halogens can form one
single bond each.
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Isomerism
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Isomerism
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Your Turn!
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Your Turn!
H C C C C C C H (CH3)2CHCH2CH2CH2CH3
H H H H H H
H H CH3 H H H
CH3CH2CHCH3CH2CH2CH3
H C C C C C C H
35
H H H H H H
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40
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Your Turn!
H H CH3
H C C C OH
H H CH3
41
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Your Turn!
1o
H H CH3
1o 2o 3o
H C C C OH
H H CH3
1o
42
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Your Turn!
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Your Turn!
2-methylhexane
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• Oxidation-reduction
• Substitution
• Addition
• Elimination
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Your Turn!
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Your Turn!
Elimination
59
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Reactions of Alkanes
Decomposition Cracking
Rearrangement Isomerization 60
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Reactions of Alkanes
Combustion (oxidation)
Alkanes are a valuable energy source due to their ability to
react with oxygen . Alkanes release a large amount of
energy as shown here.
Reactions of Alkanes
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Reactions of Alkanes
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Reactions of Alkanes
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Reactions of Alkanes
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The chlorination of methane with excess chlorine can
produce each of the compounds shown in Table 19.5.
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Reactions of Alkanes
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Reactions of Alkanes
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Reactions of Alkanes
Overall Reaction
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Reactions of Alkanes
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Reactions of Alkanes
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Reactions of Alkanes
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Your Turn!
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Your Turn!
77
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Your Turn!
CH3CHCH2CH3 + Cl Cl CH3CHCH2CH3 + Cl
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Your Turn!
2 Cl Cl Cl
Cl
Cl + CH3CHCH2CH3 CH3CHCH2CH3
CH3CHCH2CH3
CH3CHCH2CH3 + CH3CHCH2CH3
CH3CHCH2CH3
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Sources of Alkanes
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Gasoline is a mixture of
hydrocarbons. Without
additives it causes
knocking which is a
detonation of the air-fuel
mixture in an engine.
Figure 19.8 Uses of petroleum
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Cycloalkanes
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Cycloalkanes
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Cycloalkanes
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Cycloalkanes
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Cycloalkanes
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Figure 19.10 Ball-and-stick models of cyclopropane, hexane,
and cyclohexane. In cyclopropane, all the carbon atoms are in
one plane (bond angles = 60° instead of 109.5° ).
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The cyclohexane molecule is puckered (as shown in the
chair conformation) with bond angles about 109.5° as
found in hexane.
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Cycloalkanes
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Cycloalkanes
Cycloalkanes
Cycloalkanes
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Cycloalkanes
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Your Turn!
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Your Turn!
1-bromo-2-methylcyclopentane
97
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Your Turn!
CH2CH3
1,1-dichloro-3-ethylcyclohexane
98
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Chapter 19 Summary
Chapter 19 Summary
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Chapter 19 Summary
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Chapter 19 Summary
102