Organic Chemistry: Zumdahl Chapter 22

Organic Chemistry
Zumdahl Chapter 22
Alkanes: Saturated Hydrocarbons

Hydrocarbons are molecules composed of carbon & hydrogen
Each carbon atom forms 4 chemical bonds
A saturated hydrocarbon is one where all C - C bonds are single
bonds & the molecule contains the maximum number of H-atoms
Saturated hydrocarbons are called ALKANES
Normal vs Branched Alkanes

NORMAL alkanes consist of
continuous chains of carbon
CH2
CH2
CH3
CH2
CH3
atoms
Alkanes that are NOT
continuous chains of carbon
atoms contain branches
CH3
CH2
CH
CH3
The longest continuous chain
of carbons is called the
CH3
parent chain
Structural Isomerism
Structural isomers are
molecules with the same
chemical formulas but different
molecular structures - different
connectivity.
They arise because of the many
ways to create branched
hydrocarbons.
a.k.a. Constitutional Isomers
CH3
CH2
CH2
CH2
CH3
n-pentane, C5H12
CH3
CH2
CH
CH3
CH3
2-methlbutane, C5H12
The First 10 Normal Alkanes

Name
Formula
Methane CH4
B.P.
10
-183 -162 1
Pentane
C5H12 -130
36
Hexane
C6H14 -95
68
174
75
-91 are
98 9Liquids
C5C H- C16
Octane
C H -57 126 18
at
Room
Temperature
Nonane C H -54 151 35
Heptane
16
18
20
# Structural Isomers
C H - -172
-89 1Gases
C1
C4 are
Propane C H -187 -42 1
at
Room
Temperature
Butane
C H -138 0
2
Ethane
M.P.
Decane
C10H22 -30
IUPAC Rules for

Naming Branched Alkanes
Find and name the parent chain in the hydrocarbon - this
forms the root of the hydrocarbon name
Number the carbon atoms in the parent chain starting at the
end closest to the branching
Name alkane branches by dropping the ane from the
names and adding yl. A one-carbon branch is called
methyl, a two-carbon branch is ethyl, etc
When there are more than one type of branch (ethyl and
methyl, for example), they are named alphabetically
Finally, use prefixes to indicate multiple branches
Example 1: 2,2-dimethylpentane
2
4
The parent chain is indicated by
CH2 5
CH2 3
1
the ROOT of the name CH3
CH2
pentane.
pentane This means there are CH3
5 carbons in the parent chain.
dimethyl
dimethyl tells us that there are TWO
CH3
methyl branches on the parent chain.
A methyl branch is made of a single
CH2
C
carbon atom.
CH3
CH2
CH3
2,2-
2,2 tell us that BOTH methyl
CH3
branches are on the second carbon
atom in the parent chain.
4
Example 2: 3-ethyl-2,4-dimethylheptane
2

CH2 5
CH2 3
1
the ROOT of the name CH2
CH2
CH3
heptane.
heptane This means there are
7 carbons in the parent chain.
H2C 6
CH3
CH3
CH
CH
CH3
CH3
CH3
2,4-dimethyl
2,4-dimethyl tells us there are
TWO methyl branches on the
parent chain, at carbons #2 and #4.
CH
CH2
CH2
3-ethyl-
3-ethyl tell us there is an ethyl
CH2
branch (2-carbon branch) on
CH3
carbon #3 of the parent chain.
Example 3: 2,3,3-trimethyl-4-propyloctane
the ROOT of the name - octane.
octane
This means there are 8 carbons
in the parent chain.
5
4
6
7
CH3
5
4
6
7
2,3,3-trimethyl
2,3,3-trimethyl tells us there are
CH3THREECmethyl branches
CH2 - one on
CH #2 andCH
CH2#3.
carbon
two on carbon
8
CH3
CH3
CH2
CH2
4-propyl-
4-propyl tell us there is a propyl
CH3
CH
branch (3-carbon branch)
2 on
carbon #4 of the parent chain.
CH3
Example 4: Name the molecules shown!

CH3
parent chain has 5 carbons pentane

CH
CH2
two methyl branches - start
CH3
CH
CH3
counting from the right - #2 and #3
2,3-dimethylpentane
CH3
parent chain has 8 carbons - octane

two methyl branches - start counting
from the left - #3 and #4
one ethyl branch - #5
name branches alphabetically
5-ethyl- 3,4-dimethyl octane
HOMEWORK ASSIGNMENT
Read Zumdahl section 22-1
make notes on REACTIONS OF ALKANES and
on CYCLIC ALKANES
Copy table 22.2 on page 1040
Pay attention to sample exercises!
Answer end-of-chapter problems:

problems
15, 16, 17, 18
Alkanes Review - Cycloalkanes

A cycloalkane is made of a hydrocarbon chain
that has been joined to make a ring.
H2
C
109.5 bond angle
CH3
CH2
CH3
n-propane
C3H8
H2C
60 bond angle
unstable!!
CH2
cyclopropane
C3H6
Note that two hydrogen atoms were lost in forming the

ring!
Other Cycloalkanes
Angle
(ring) Strain - results from compression of
cyclobutane
the
bondbond
angles.angles
Cyclopropane has the
C4internal
H8 - ~90
greatest angle strain (60 bond angles) while the
strain is eliminated in cyclohexane.
cylcopentane
C5H10 ~109.5 bond angles
Torsional Strain - a barrier to free rotation around

single bonds, due to the eclipsing of atoms in a
molecule. This results when atoms are brought
cyclohexane
too
close together in a particular conformation of
6H12 = 109.5 bond angles
aCmolecule.
Cycloalkanes: Cis-Trans Isomerism

The
Trans-isomer
is the molecule with
Consider
1,2-dimethylcycloalkane
- abranches
moleculeon
thatOPPOSITE
illustrates
sides
of the ring
GEOMETRIC
ISOMERISM - compounds with the same molecular
formula
and connectivity
but differ
their geometries.
The
Cis-isomer
is the molecule
within branches
on the SAME SIDE
of
themolecule
ring. on the left shows the two methyl branches on
The
OPPOSITEisomerism
SIDES ofisthe
ring.
molecule on
the right shows
Cis-Trans
one
typeThe
of geometric
isomerism
the two methyl branches on the SAME SIDE of the ring.
Trans
Trans-1,2-dimethylcyclopentane
-1,2-dimethylcyclopentane
Cis
Cis-1,2-dimethylcyclopentane
-1,2-dimethylcyclopentane
Cis-Trans Isomers - Examples

cis-1,3-dimethylcyclobutane
Cl
1-chloro-1-methylcyclohexane
cis-1,2-dichlorocyclohexane
CH2
H3C
CH
3
CH2
5
Cl
Cl
CH
1
CH3
4
trans-1-ethyl-2-methylcyclopropane
Cyclohexane - Boat & Chair Conformations

Cyclohexane is NOT a planar molecule. To achieve its
109.5 bond angles and reduce angle strain, it adopts
several different conformations.
The BOAT and CHAIR (99%) are two conformations
Alkenes & Alkynes

Alkenes are
hydrocarbons that
contain at least one
carbon-carbon double
bond
Alkynes are
hydrocarbons that
contain at least one
carbon-carbon triple
bond
The suffix for the parent

chains are changed from
ane to ene and yne
e.g. ethene, propyne
Where it is ambiguous,
the BONDS are
numbered like branches
so that the location of
the multiple bond may
be indicated
Alkenes & Alkynes: Examples

H2C
CH2
HC
ethene
H3C
16
1-butene
H2
C
CH
H2C
C
H
H2C
CH3
ethyne
propyne
CH
H
C
CH3 H3C
propene
2-pentyne
C
CH2
CH3
Cis-Trans IsomerismAgain!
Like rings, alkenes and alkynes show
restricted rotation - this time about the
multiple bonds
Because of the 120 bond angles in
alkenes, cis-trans isomerism is possible
If one of the carbons in the double bond have
two of the same substituents, there is NO cistrans isomerism!
Remember that trans means opposite sides
of the double bond and cis means the same
side of the bond!
Use molar mass to prioritize the substituents
to decide cis-trans isomerism
cis-2-butene
cis-2-butene
HH
CC
HH33CC
HH
CC
CH3
CH
3
trans-2-butene
trans-2-butene
CH3
CH
3
H
H
CC CC
HH
HH33CC
Name those alkenes...

H
C
H
C
cis-4-methyl-2-pentene
HC
CH CH
3
2-methyl-2-hexene
H3C
trans-2-bromo-3-methylBr 2-pentene
H2
C
H2cyclopentene
C
CH2
C
H
C
H
cis-3-heptene
Homework Assignment
READ sections 22.2 (Alkenes & Alkynes), 22.3
(Aromatic Hydrocarbons) and 22.4 (The
Petrochemical industry)
Dont get hung up on and bonds
Copy figure 22.11 and 22.12
Summarize the use of ortho, meta, para prefixes when
naming benzene derivatives
Make notes on section 22.4 - the Petrochemical Industry
Complete Questions 19 - 25, 27, 29, 31, 32, 54 - 56

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Organic Chemistry

Alkanes: Saturated Hydrocarbons

Normal vs Branched Alkanes

The First 10 Normal Alkanes

IUPAC Rules for

The parent chain is indicated by

Example 4: Name the molecules shown!

parent chain has 5 carbons pentane

parent chain has 8 carbons - octane

5-ethyl- 3,4-dimethyl octane

Answer end-of-chapter problems:

Alkanes Review - Cycloalkanes

109.5 bond angle

Note that two hydrogen atoms were lost in forming the

Torsional Strain - a barrier to free rotation around

Cycloalkanes: Cis-Trans Isomerism

Cis-Trans Isomers - Examples

Cyclohexane - Boat & Chair Conformations

Alkenes & Alkynes

The suffix for the parent

Alkenes & Alkynes: Examples

Name those alkenes...

Complete Questions 19 - 25, 27, 29, 31, 32, 54 - 56

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