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Organic ChemistryChapter 11
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
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11.1
Common Elements in Organic Compounds
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11.1
Classification of Hydrocarbons
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11.2
Alkanes
Alkanes have the general formula _________ where n = 1,2,3,…
• only single covalent bonds
• _____________________________ because they contain the maximum number of hydrogen atoms that can bond with the number of carbon atoms in the molecule
CH4 C2H6 C3H8
___________ ___________ ___________
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11.2
_________________________ are molecules that have the same molecular formula but different structures
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How many structural isomers does pentane, C5H12, have?
C C C C C
H H H H H
H
HHHHH
H
C C C C
H CH3 H H
H
HHHH
H
C C C
H CH3 H
H
HH
H
CH3
n-pentane
2-methylbutane
2,2-dimethylpropane
11.2
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11.2
_____________ _____________
1. The parent name of the hydrocarbon is that given to the longest continuous chain of carbon atoms in the molecule.
CH3 CH2 CH2 CH CH2 CH2 CH3
CH3
1 2 3 4 5 6 74-methylheptane
2. An alkane minus one hydrogen atom is called an ______ group
CH4
CH3
methane
methyl
Common Alkyl Groups
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11.2
Alkane Nomenclature
The First 10 Straight-Chain Alkanes
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11.2
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 CH CH2 CH2 CH3
CH3
1 2 3 4 5
2-methylpentane
CH3 CH2 CH2 CH CH3
CH3
1 2 3 4 5
4-methylpentane
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11.2
Alkane Nomenclature
4. Use prefixes di-, tri-, tetra-, when there is more than one alkyl branch of the same kind.
CH3 CH CH CH2 CH2 CH3
CH3
1 2 3 4 5 6
CH3
2,3-dimethylhexane
CH3 CH CH CH2 CH2 CH3
CH3
1 2 3 4 5 6
CH3
3,3-dimethylhexane
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11.2
Alkane Nomenclature
5. Use previous rules for other types of substituents.
CH3 CH CH CH3
Br
1 2 3 4
NO2
2-bromo-3-nitrobutane
CH2 CH CH CH3
Br
1 2 3 4
NO2
1-bromo-3-nitrobutane
Names of Common Groups
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What is the IUPAC name of the following compound?
11.2
1 2 3 4 5 6 7 8CH3 CH CH2 CH CH2 CH2 CH3
C2H5
CH2
CH3
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11.2
What is the structure of 2-propyl-4-methylhexane?
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11.1
Classification of Hydrocarbons
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11.2
Alkane Reactions
CH4 (g) + 2O2 (g) CO2 (g) + 2H2O (l) H0 = -890.4 kJ
_______________
________________
CH4 (g) + Cl2 (g) CH3Cl (g) + HCl (g)light
Cl2 + energy Cl• + Cl•
Cl• + C HH
H
H
C H
H
H
• + HCl
CH
H
H
• + Cl Cl C ClH
H
H
+ Cl•
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11.2
________________ ________________
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11.2
Alkanes
Alkanes whose carbon atoms are joined in rings are called
___________________________________.
They have the general formula CnH2n where n = 3,4,…
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11.2
__________________
___________ have the general formula CnH2n where n = 2,3,…
• contain at least one carbon-carbon double bond
• also called __________________
CH2 CH CH2 CH3
1-butene
CH3 CH CH CH3
2-butene
C C
Cl Cl
H H
C C
Cl H
H Cl
_____ -dichloroethylene _____-dichloroethylene
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11.2
Alkene Reactions
Cracking
Addition Reactions
CH2 CH2 (g) + HBr (g) CH3 CH2Br (g)
CH2 CH2 (g) + Br2 (g) CH2Br CH2Br (g)
C2H6 (g) CH2 CH2 (g) + H2 (g)Pt
catalyst
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11.2
____________________
_________ have the general formula CnH2n-2 where n = 2,3,4,…
• contain at least one carbon-carbon triple bond
1-butyne 2-butyne
CH C CH2 CH3 CH3 C C CH3
Production of acetylene
CaC2 (s) + 2H2O (l) C2H2 (g) + Ca(OH)2 (aq)
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11.2
Alkyne Reactions
Addition Reactions
Hydrogenation
CH CH (g) + H2 (g) CH2 CH2 (g)
CH CH (g) + HBr (g) CH2 CHBr (g)
CH CH (g) + Br2 (g) CHBr CHBr (g)
CH CH (g) + 2Br2 (g) CHBr2 CHBr2 (g)
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11.3
_________________ Hydrocarbons
C
CC
CC
C
H
H
H
H
H
H
C
CC
CC
C
H
H
H
H
H
H
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11.3
Aromatic Compound Nomenclature
CH2CH3
ethylbenzene
Cl
chlorobenzene
NH2
aminobenzene
NO2
nitrobenzene
12
3
4
5
6
Br
Br
1,2-dibromobenzene
Br
Br
1,3-dibromobenzene
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11.3
Aromatic Compound Reactions
H
H
H
H
H
H
Br
H
H
H
H
H
+ HBr+ Br2
FeBr3
catalyst
H
H
H
H
H
H
CH2CH3
H
H
H
H
H
+ HCl+ CH3CH2ClAlCl3
catalyst
Substitution reaction
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11.3
Polycyclic Aromatic Hydrocarbons
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11.4
Functional Group Chemistry
___________________ contain the hydroxyl functional group and have the general formula R-OH.
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C6H12O6 (aq) 2CH3CH2OH (aq) + 2CO2 (g)enzyme
CH2 CH2 (g) + H2O (g) CH3CH2OH (g)H2SO4
Biological production of ethanol
Commercial production of ethanol
Metabolic oxidation of ethanol
CH3CH2OH CH3CHO + H2
alcohol dehydrogenase
11.4
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11.4
Functional Group Chemistry
_________________ have the general formula R-O-R’.
CH3OH + HOCH3 CH3OCH3 + H2OH2SO4
catalyst
Condensation Reaction
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11.4
Functional Group Chemistry
___________________ and ______________ contain the carbonyl ( ) functional group.
R C H
O
• ________ have the general formula
R C R’
O
• ______ have the general formula
H C H
O
H C
O
CH3 C
O
CH3H3C
___________ ___________ ___________
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11.4
Functional Group Chemistry
________________________ contain the carboxyl ( ) functional group.
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11.4
Functional Group Chemistry
_________________ have the general formula
R’— , where R is a hydrocarbon group.
CH3COOH + HOCH2CH3 CH3 C O CH2CH3 + H2O
O
ethyl acetate
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11.4
Functional Group Chemistry
_________________________ are organic bases with the
general formula _________.
CH3NH2 + H2O RNH3+ + OH-
CH3CH2NH2 + HCl CH3CH2NH3+Cl-
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11.4
Important Functional Groups and Their Reactions