Simple Organic Chemistry

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Simple Organic Chemistry
Basic Structure and Nomenclature
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First Ten Alkanes
Alkane CnH2n2
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Straight Chain Alkanes arent Straight
C C bonds are sp3 hybridized
Butane, C4H10
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Structural Shorthand
Explicit hydrogens (those required to complete
carbons valence) are usually left off of
drawings of hydrocarbons
C1
C2
C3
C4
C1
C3
C4
C2
Line intersections represent carbon atoms
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Structural Isomers
Isomers are molecules with the same chemical
formula, but different organization of atoms
(different bonding)
n-Pentane, C5H12
Isopentane, C5H12
Neopentane, C5H12
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Cyclic Alkanes
Cyclopropane, C3H6
Cyclobutane, C4H8
Cyclopentane, C5H10
Cyclohexane, C6H12
Cycloheptane, C7H14
Remember, explicit hydrogens are left out
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Page 697, 1 and 2
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Rules for Naming Alkanes (Nomenclature)
For a branched hydrocarbon, the longest
continuous chain of carbon atoms gives the root
name for the hydrocarbon
1
2
3
4
4 carbon chain butane
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Rules for Naming Alkanes (Nomenclature)
When alkane groups appear as substituents, they
are named by dropping the -ane and adding -yl.
CH3 Methyl
CH2CH3 Ethyl
CH2CH2CH3 Propyl
CH2CH2CH2CH3 Butyl
Methyl
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Rules for Naming Alkanes (Nomenclature)
The positions of substituent groups are specified
by numbering the longest chain of carbon atoms
sequentially, starting at the end closest to the
branching.
1
2
3
4
Methyl
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Rules for Naming Alkanes (Nomenclature)
The location and name of each substituent are
followed by the root alkane name. The
substituents are listed in alphabetical order
(irrespective of any prefix), and the prefixes
di-, tri-, etc. are used to indicate multiple
identical substituents.
1
2
3
4
Name
2-methylbutane
Methyl
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Nomenclature Practice
Name this compound
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9 carbons nonane
2
4
3
5
6
7
8
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Step 1 For a branched hydrocarbon, the longest
continuous chain of carbon atoms gives the root
name for the hydrocarbon
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Nomenclature Practice
Name this compound
9 carbons nonane
1
2
4
3
5
6
CH3 methyl
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chlorine chloro
8
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Step 2 When alkane groups appear as
substituents, they are named by dropping the -ane
and adding -yl.
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Nomenclature Practice
Name this compound
9 carbons nonane
1
2
4
3
5
6
CH3 methyl
7
chlorine chloro
8
9
1
9
NOT
9
1
Step 3 The positions of substituent groups are
specified by numbering the longest chain of
carbon atoms sequentially, starting at the end
closest to the branching.
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Nomenclature Practice
Name this compound
9 carbons nonane
1
2
4
3
5
6
CH3 methyl
7
chlorine chloro
8
9
2-chloro-3,6-dimethylnonane
Step 4 The location and name of each
substituent are followed by the root alkane name.
The substituents are listed in alphabetical order
(irrespective of any prefix), and the prefixes
di-, tri-, etc. are used to indicate multiple
identical substituents.
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Alkenes Contain Carbon-CarbonDouble bonds
1 ? bond
Ethene
1 ? bond
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Alkynes Contain Carbon-CarbonTriple Bonds
1 ? bond
Ethyne
1 ? bond
1 ? bond
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Reactions of Alkenes and Alkynes
Hydrogenation
Propene
Propane
Halogenation
1-Pentene
1-2-dibromopentene
Polymerization
Small molecules are joined together to form a
large molecule
Polyethylene
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Aromatic Hydrocarbons
Cyclic unsaturated hydrocarbons with delocalized
electrons
The simplest aromatic hydrocarbon is benzene
(C6H6)
OR
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Geometric Isomerism in Aromatics
ortho (o-) two adjacent
substituents
o-dichlorobenzene

meta (m-) one carbon between
substituents
m-dichlorobenzene
para (p-) two carbons between
substituents
p-dichlorobenzene
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