Lecture Four

ALKENES
Abdikarim
3.Alkenes
• Alkenes are hydrocarbons with the general

formula CnH2n and contain a carbon-carbon
double bond. (also called olefins)
– The simplest alkene is ethylene.
H H
C C
H H
First 10 Alkenes in Series
Hydrocarbon Molecular Formula

Ethene C2H4
Propene C3H6
Butene C4H8
Notice: There is no
Pentene CH
alkene corresponding to
the methane of5the10
alkane series. That is
Hexene CH
b/c there must 6be at
12
least 2 carbon atoms to
Heptene CH
form a double bond.
7 14
Octene C8H16
Nonene C9H18
Decene C10H20
Rules for Naming Alkenes
1. Name the longest chain that contains the double bond or

double bonds. The name of the chain will end in –ene.
2. Number this longest chain so the C=C bond or bonds
has/have the lowest number.
3. The first C of the C=C bond (for C=C bond to have lowest
number) identifies the positional location of the double bond.
4. Name the attached functional groups.
5. Combine the names of the attached groups and longest chain,
the same as you would with alkanes.
6. For multiple double bonds, indicate the locations of all
multiple bonds, use numeric prefixes indicating number of
double bonds (-diene, -triene).
Naming Alkenes
• Step 1: Name the longest chain that contains the C=C bond.
Use the IUPAC root and the –ene ending.
• Step 2: Number the longest chain so the C=C bond gets the
lowest number possible.
• Step 3: Locate the C=C bond with the lower-numbered
carbon.
Examples:
1 2 3 4
CH3-CH=CH-CH3
2-butene
6 5 4 3 2 1
CH3-CH2-CH2-CH=CH-CH3
2-hexene
Naming Alkenes (continued)
• Step 4: Locate and name attached groups.
• Step 5: Combine all the names.
What’s My Name?
GEOMETRICAL ISOMERISM IN ALKENES
Introduction
• an example of stereoisomerism
• found in some, but not all, alkenes
• occurs due to the RESTRICTED ROTATION OF C=C
bonds
• get two forms....
CIS TRANS
Groups/atoms are on the Groups/atoms are on OPPOSITE
SAME SIDE of the double bond SIDES across the double bond
Isomers - have different physical properties - e.g. boiling points, density

- have different chemical properties - in most cases
GEOMETRICAL ISOMERISM
How to tell if it exists
Two different Two different

GEOMETRICAL
atoms/groups atoms/groups
ISOMERISM
attached attached

Two similar Two similar
atoms/groups atoms/groups
Once you get two similar
attached attached
atoms/groups attached to
one end of a C=C, you
cannot have geometrical

Two similar Two different
atoms/groups atoms/groups isomerism
attached attached
Two different Two different

atoms/groups
attached
atoms/groups
attached  GEOMETRICAL
ISOMERISM
Isomerism in butene
Geometric (cis-trans) Isomerism in Alkenes
• By definition, must have 2 different groups attached to each double bonded
carbon.
Geometric Isomers?
H H H CH3
C C C C Yes
H3C CH3 H3C H
H H H3C CH3
C C C C
No
H3C CH3 H H
H H H CH3
C C C C No
H3C H H H
Which of the following can exhibit cis-trans isomerism?

Cl-CH=CH-Cl CH2=CHCH3 Cl-CH=CHCH3
PHYSICAL PROPERTIES OF ALKENES
Boiling point trends are similar to those shown in alkanes

increases as they get more carbon atoms in their formula
more atoms = greater intermolecular Van der Waals’ forces
greater intermolecular force = more energy to separate molecules
greater energy required = higher boiling point
the lower members are gases at room temperature and pressure
cyclohexene C6H10 is a liquid
for isomers, greater branching = lower boiling point
C2H4 (- 104 °C) C3H6 (- 48°C) ....... C6H10 (83°C)
Melting point general increase with molecular mass

the trend is not as regular as that for boiling point.
Solubility alkenes are non-polar so are immiscible (don’t mix with) with water
miscible with most organic solvents.
ALKENES REACTIONS
Oxidation Reactions of Alkenes
 Because alkenes are hydrocarbons, they
undergo complete combustion reactions
with oxygen.
Addition reaction
Of alkenes
• Alkenes are more reactive than alkanes because
many reactants add to the double bond.
– An addition reaction is a reaction in which

parts of a reactant are added to each carbon
atom of a carbon-carbon double bond which
converts to a carbon-carbon single bond.
Addition Reactions
1. Halogenations: Addition of a Halide (fluorine, chlorine,

bromine, iodine).
CH3CH2CH CH2 + Br-Br CH3CH2CH CH2
Br Br
1-butene 1,2-dibromobutane
2. Hydrogenation: Metal (Pt, Pd or Ni) catalyzed addition of

hydrogen atoms to C=C bond.
Pt
CH3CH CHCH3 + H2 CH3CH CHCH3
H H
2-butene butane
Markovnikov’s Rule
In the ionic addition of an acid to the carbon-

carbon double bond of an alkene, the hydrogen
of the acid attaches itself to the carbon atom
which already holds the greater number of
hydrogen's.
– “Them that has, gets!”
– “The richer get richer!”
(V. W. Markovnikov -- 1838
- 1904)
Addition of HBr or HCl
Markovnikov Addition
CH3 H Br H
HBr CH3 H
C C C C
CH3 H CH3 H
Markovnikov
H Br
CH3 H
C C
CH3 H
not formed

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ALKENES

• Alkenes are hydrocarbons with the general

Hydrocarbon Molecular Formula

1. Name the longest chain that contains the double bond or

Isomers - have different physical properties - e.g. boiling points, density

How to tell if it exists

Two different Two different

Two different Two different

Which of the following can exhibit cis-trans isomerism?

Boiling point trends are similar to those shown in alkanes

C2H4 (- 104 °C) C3H6 (- 48°C) ....... C6H10 (83°C)

Melting point general increase with molecular mass

– An addition reaction is a reaction in which

1. Halogenations: Addition of a Halide (fluorine, chlorine,

2. Hydrogenation: Metal (Pt, Pd or Ni) catalyzed addition of

In the ionic addition of an acid to the carbon-

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