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Organic Chemistry
Chapter 11
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Common Elements in Organic Compounds
11.1
Classification of Hydrocarbons
11.1
Alkanes
Alkanes have the general formula CnH2n+2 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
___________
11.2
___________ ___________ are molecules that have the
same molecular formula but different structures
11.2
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
C
C
H
CH3 H
n-pentane
H
H
H
CH3 H
H
C
C
C
C
H
H
H
H
2-methylbutane
H
C
H
2,2-dimethylpropane
11.2
Alkane Nomenclature
1. The parent name of the hydrocarbon is that given to the
___________ ___________ chain of carbon atoms in the
molecule.
CH3
CH3
1
CH2
2
CH2
3
CH
4
CH2
5
CH2
6
2. An alkane less one hydrogen atom
is an ___________ group.
11.2
CH4
methane
CH3
methyl
CH3 4-methylheptane
7
Alkane Nomenclature
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 ___________
___________ for the locations of the branches.
CH3
CH3
1
CH
2
CH2
3
CH2
4
CH3
5
CH3
2-methylpentane
CH3
1
CH2
2
CH2
3
CH
4
CH3
5
4-methylpentane
11.2
Alkane Nomenclature
4. Use prefixes di-, tri-, tetra-, when there is more than one
alkyl branch of the same kind.
CH3
1
CH3
CH3
CH
CH
2
3
CH2
CH2
4
CH3
5
6
______________________
CH3
CH3
1
CH
2
C
3
CH2
4
CH2
5
CH3
6
CH3
______________________
11.2
Alkane Nomenclature
5. Use previous rules for other types of substituents.
CH3
1
Br
NO2
CH
CH
2
3
CH3
4
2-bromo-3-nitrobutane
Br
CH2
1
NO2
CH2
2
CH
3
CH3
4
1-bromo-3-nitrobutane
11.2
What is the IUPAC name of the following compound?
CH3
CH3
1
CH
2
C2H5
CH2
3
CH
4
CH2
5
CH2
6
CH2
7
CH3
8
______________________
What is the structure of 2-propyl-4-methylhexane?
11.2
Alkane Reactions
CO2 (g) + 2H2O (l) DH0 = -890.4 kJ
CH4 (g) + 2O2 (g)
light
CH4 (g) + Cl2 (g)
CH3Cl (g) + HCl (g)
Cl2 + energy
Cl• + Cl•
H
H
Cl• + H
C
H
H
•C
H
H
H
C • + Cl
H
H + HCl
H
Cl
H
C
H
Cl + Cl•
11.2
achiral
chiral
11.2
Cycloalkanes
Alkanes with carbon atoms joined in rings are ______________.
They have the general formula CnH2n where n = 3,4,…
11.2
Cycloalkanes
11.2
___________
___________ have the general formula CnH2n where n = 2,3,…
• contain at least one carbon-carbon double bond
• also called ___________
CH
CH2
CH2
CH3
_______________
Cl
Cl
C
H
CH3
CH
Cl
H
C
______________________
CH3
_______________
C
H
CH
H
C
Cl
______________________
11.2
Cis-Trans Isomerization in the Vision Process
11.2
Alkene Reactions
C2H6 (g)
Pt
catalyst
CH2
CH2 (g) + H2 (g)
CH2
CH2 (g) + HBr (g)
CH3
CH2
CH2 (g) + Br2 (g)
CH2Br
CH2Br (g)
CH2Br (g)
11.2
___________
__________ have the general formula CnH2n-2 where n = 2,3,4,…
• contain at least one carbon-carbon triple bond
CH
C
CH2
1-butyne
CH3
CH3
C
C
CH3
2-butyne
Production of
CaC2 (s) + 2H2O (l)
C2H2 (g) + Ca(OH)2 (aq)
11.2
Alkyne Reactions
CH
CH (g) + H2 (g)
CH2
CH2 (g)
CH
CH (g) + HBr (g)
CH2
CH
CH (g) + Br2 (g)
CHBr
CH
CH (g) + 2Br2 (g)
CHBr2
CHBr (g)
CHBr (g)
CHBr2 (g)
11.2
Chemistry In Action: Ice That Burns
___________ Hydrocarbons
H
H
H
H
C
C
C
C
C
C
H
H
H
H
H
C
C
C
C
C
C
H
H
H
11.3
Aromatic Compound Nomenclature
ethylbenzene
CH2CH3
aminobenzene
NH2
Cl
chlorobenzene
6
2
5
3
4
nitrobenzene
Br
Br
1
NO2
Br
Br
1,2-dibromobenzene
1,3-dibromobenzene
11.3
Aromatic Compound Reactions
H
Br
H
H
+ Br2
H
H
H
FeBr3
catalyst
+ HBr
H
H
H
H
H
H
CH2CH3
H
H
+ CH3CH2Cl
H
H
H
H
H
AlCl3
catalyst
+ HCl
H
H
H
11.3
Polycyclic Aromatic Hydrocarbons
11.3
Functional Group Chemistry
___________ contain the hydroxyl functional group and have the
general formula R-OH.
11.4
Biological production of ethanol
C6H12O6 (aq)
enzyme
2CH3CH2OH (aq) + 2CO2 (g)
Commercial production of ethanol
CH2 CH2 (g) + H2O (g)
H2SO4
CH3CH2OH (g)
Metabolic oxidation of ethanol
CH3CH2OH
alcohol dehydrogenase
CH3CHO + H2
11.4
Functional Group Chemistry
___________ have the general formula R-O-R’.
CH3OH + HOCH3
H2SO4
catalyst
CH3OCH3 + H2O
11.4
Functional Group Chemistry
O
___________ & ___________ contain the carbonyl ( C
functional group.
O
)
• ________ have the general formula R C H
O
• _______ have the general formula R C R’
O
O
O
H C H
H C CH3
H3C C CH3
___________
___________
___________
11.4
Functional Group Chemistry
___________ ___________ contain the carboxyl ( -COOH )
functional group.
11.4
Functional Group Chemistry
___________ have the general formula R’COOR, where R is a
hydrocarbon group.
O
CH3COOH + HOCH2CH3
CH3 C O CH2CH3 + H2O
ethyl acetate
11.4
Functional Group Chemistry
___________ are organic bases with the general formula R3N.
CH3NH2 + H2O
CH3CH2NH2 + HCl
RNH3+ + OH-
CH3CH2NH3+Cl-
11.4
11.4
Chemistry In Action: The Petroleum Industry
Crude Oil