CH2.2 - Alkene

Unsaturated Hydrocarbon - Alkenes

Chapter 2.2
Alkenes
Nomenclature of Alkenes
Naming of Cycloalkenes
Geometric Isomers
Properties of Alkenes
Synthesis of Alkenes
Principal Reactions of Alkenes

Introduction
Classification of Hydrocarbon

Hydrocarbon
Aromatic
Aliphatic
Alkanes
Alkenes
Alkynes
CycloalkanesCycloalkenes
Saturated
Unsaturated
Hydrocarbons
Hydrocarbons
Aliphatic
Aliphatic
Alkenes are
hydrocarbons that
contain a carboncarbon double bond.
H
H
C
Alkenes
Alkenes
H
C
H
Hydrocarbons
Hydrocarbons
Aliphatic
Aliphatic
Alkenes whose
carbon atoms are
joined in rings.
CycloAlkenes
CycloAlkenes
Alkenes
Unsaturated hydrocarbon
Contain carbon carbon double bonds
Alkenes
General formula
Aliphatic hydrocarbons
CYCLOALKENES
Alkenes whose carbon atoms are joined in rings
General formula Cn H2n-2 where n =3,4,5..
Eg:
Cyclopentene C5H8
Cyclobutene C4H6
CH3
CH3
1,3- dimethylcyclopentene
Naming Alkenes
We must account for double bond:
Longest chain must contain the double bond
Number of carbons so that the double bond has the lowest
number
Indicate the position of the double bond
Change ending to - ene
use the same rules for the side chains and halides
The ending of the alkenes with more than one

double bond should be change from -ene to:
diene if there are two double bonds
triene if there are three double bonds
1
H2C
1
H2C
CH CH
2
CHCH
1,3-butadiene
CH2
4
CHCH
CHCH3
1,3,5-heptatriene
Naming cycloalkenes
1
5
CH3
6-Ethyl-1-methylcyclohexene
CH2CH3
1) Replace the -ane ending of the cycloalkane

having the same number of carbons by -ene.
2) Number through the double bond in the
direction that gives the lower number to the
first-appearing substituent.
Number substituted cycloalkenes in the way that gives the
carbon atoms of the double bond the 1 and 2 positions.

That also gives the substituent groups the lower numbers at
the first point of difference.
1
CH3
2
4
H3C
CH3
1-methylcyclopentene
3,5-dimethylcyclohexene
Alkenes nomenclature must specify whether a

given molecule is cis or trans if it is a
geometric isomer
Eg:
CH3
CH3
C=C
H
cis-2-butene
CH3CH2
C=C
H
CH2CH3
trans-3-hexene
CH2CH3
CH3CH2
C=C
H
CH2CH2CH3
trans-4- ethyl 3-heptene
CH2CH2CH3
CH3CH2
C=C
H
CH3
cis-4-methyl-3-heptene
Geometric Isomer
Trigonal planar
2-butene
However, Cis trans stereoisomerism (geometry isomer) in

alkenes is not possible when :
When one of the doubly bonded carbons bears two identical

substituents
Using the prefix E and Z

Although the prefixes cis and trans can be used to
distinguish disastereomers when two alkyl groups are
bonded to the C C , they cannot be used when there
are three or four alkyl groups bonded to the C C.
A completely unambiguous system for specifying double
bond stereochemistry has been adopted by the IUPAC based
on an atomic number criterion for ranking substituents on the
doubly bonded carbons.
When atoms of higher atomic number are on the same side of

double bond, we say that the double bond has the Z configuration.
Higher
CI
Br
C
Lower
Higher
Lower
Z configuration
When atoms of higher atomic number are on opposite site of

double bond, we say that the double bond has the E configuration.
Higher
CI
F
C
Lower
Br
E configuration
* Refer to page 189 in our text book
Lower
Higher
Physical Properties
Physical Properties
Similar to alkanes
Solubility
Soluble in non polar solvent
Not soluble in water
Low density, boiling point and melting point
Properties vary based on chain size
Interesting physical properties
Alkenes with several double bonds will have a color
associated with them
Colored Alkenes
Physical Properties of Alkenes
Synthesis of alkenes
Synthesis of alkenes: elimination reactions

dehydrogenation of alkanes:
X=Y=H
dehydration of alcohols:
X = H; Y = OH
dehydrohalogenation of alkyl halides:
X = H; Y = Br, Cl
C
Y
Dehydrogenation of alkanes
Elimination of molecule H2
limited to industrial synthesis of ethylene, propene

H
Example
H
H
H
C
H
750C
ethane
H
C
+ H2
+
H
ethene (ethylene)
H2
Dehydration of alcohol
Loss of H and OH from adjacent carbons.
Acid catalyst is necessary.
C
OH
H 2O
Example
H
H
C
H
H
C
H
H2SO4
OH
ethanol
160C
H
C
C
H
ethene (ethylene)
H 2O
Regioselectivity in alcohol dehydration
H H
H OH H H
H C C C C H H2SO4 H C C C C H
H H
H
H
H H
H C H
H C H
80C
H
H
2-methyl-1-butene
2-methyl-2-butanol
10 %
H
H
H C C C C H
H
H H
+ H C H
H
2-methyl-2-butene
90 %
A reaction that can proceed in more than one

direction, but in which one direction predominates,
is said to be regioselective.
Zaitsev Rule
When elimination can occur in more than one

direction, the principal alkene is the one formed
by loss of H from the carbon having the
fewest hydrogens.
R
OH
CH3
R
CH2R
CH2R
C
2H on this carbon
only 1H on this carbon
C
CH3
Dehydrohalogenation of alkyl halides
Loss of H and halogen (X) from an alkyl halide
In the presence of strong base in solvent likewise
NaOCH3 in methanol, or KOH in ethanol
C
+ HX
Example
H
H
C
H
H
C
H
Cl
(Sodium ethoxide)
NaOCH2CH3
ethanol, 55C
Ethyl chlorides
H
C
+
H
ethene (ethylene)
HCl
Hydrogen
chloride
Reactions of alkenes
Reaction of Alkenes
Primarily reactions involve the double bond
The key reaction of double bond is addition reaction
(Breaking the bond and adding something to each carbon)
The major alkene reactions include additions of hydrogen
(H2),halogen ( CI2 or Br2), water (HOH) or hydrogen
halides (HBr or HCI)
+ A-B
A B
Reaction of Alkenes
Hydrogenation Addition of H2
Addition of a molecule of H2
Results in the formation of an alkane
Usually requires heat, pressure and a catalyst like Pt, Pd or Ni
Reaction of Alkenes
Hydration: Addition of H2O

The addition of water to an alkene
One carbon get an H, the other an OH
produces an alcohol
The reaction requires a small amount of acid to be present

to work
Reaction of Alkenes
Reaction of Alkenes
Reaction of Alkenes
Reaction of Alkenes
Hydrohalogenation
Addition of HX to an alkene
HX HF, HCI, HBr, HI
It follows Markonikovs rule where the H ends up on the
carbon with the most hydrogen to start with
Reaction of Alkenes
Reactions of alkenes
Halogenation: Addition of X2
The addition of halogen to an alkene
produces a haloalkane or alkyl halide
R C CR
X2
R C C R
X X
Simple laboratory test for unsaturation.
Ozonolysis of alkenes
1st step - reaction of alkene with ozone to form
ozonide.
2nd step - hydrolysis of ozonide to form aldehyde
and ketone.
R
R
O
C
H
R
+ O3
O
O
ozonide
R
R
C
H aldehyde
ketone R
H2O, Zn

CH2.2 - Alkene

Uploaded by

Copyright:

Available Formats

CH2.2 - Alkene

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

CH2.2 - Alkene

Uploaded by

Copyright:

Available Formats

Unsaturated Hydrocarbon - Alkenes

The ending of the alkenes with more than one

1) Replace the -ane ending of the cycloalkane

Number substituted cycloalkenes in the way that gives the

carbon atoms of the double bond the 1 and 2 positions.

Alkenes nomenclature must specify whether a

trans-4- ethyl 3-heptene

However, Cis trans stereoisomerism (geometry isomer) in

When one of the doubly bonded carbons bears two identical

Using the prefix E and Z

When atoms of higher atomic number are on the same side of

When atoms of higher atomic number are on opposite site of

* Refer to page 189 in our text book

Physical Properties of Alkenes

Synthesis of alkenes: elimination reactions

limited to industrial synthesis of ethylene, propene

A reaction that can proceed in more than one

When elimination can occur in more than one

Usually requires heat, pressure and a catalyst like Pt, Pd or Ni

Hydration: Addition of H2O

The reaction requires a small amount of acid to be present

Simple laboratory test for unsaturation.

You might also like