Alkenes and Alkynes

1
Unsaturated hydrocarbons
have fewer hydrogen atoms attached
to the carbon chain than do alkanes
are alkenes with double C=C bonds
are alkynes with triple CC bonds

2
According to VSEPR
theory:
Three groups in a double
bond are bonded at 120
angles.
Alkenes are flat because the
atoms in a double bond lie in
the same plane.

3
According to VSEPR theory:
The atoms in a triple bond have a 180 angle.

4
 The names of alkenes
use the corresponding alkane name
change the ending from -ane to -ene

Alkene IUPAC Common

H2C=CH2 Ethene Ethylene
H2C=CHCH3 Propene Propylene
Cyclohexene

General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc.
5
Ethene, or ethylene,
is the alkene C2H4
has two carbon atoms connected by a
double bond
has two H atoms bonded to each C
atom
is flat with all the C and H atoms in the
same plane
is used to accelerate the ripening of
fruits

6
The names of alkynes
use the corresponding alkane name
change the ending from -ane to -yne

Alkyne IUPAC Common

HCCH Ethyne Acetylene
HCCCH3 Propyne

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CisTrans Isomers

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In an alkene, cis and trans isomers
are possible because the double
bond
is rigid
cannot rotate
has groups attached to the carbons of
the double bond that are fixed relative
to each other

9
Cistrans isomers can be
modeled by
making a double bond with
your fingers with both thumbs
on the same side (cis isomer)
or fingers with thumbs on
opposite sides from each
other (trans isomer)

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Cistrans isomers occur when
different groups are attached to
the double bond.
In a cis isomer, groups are attached
on the same side of the double bond.
In the trans isomer, the groups are
attached on opposite sides of the
double bond.

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 The prefixes cis- or trans- are placed in front of the alkene name
when there are cistrans isomers.
cis- trans-

Br Br Br H
C C C C
H H H Br
cis-1,2-Dibromoethene trans-1,2-Dibromoethene

12
 Cistrans isomers do not occur if a carbon atom in the double
bond is attached to identical groups.

(not cis or trans) (not cis or trans)

13
A pheromone
is a chemical messenger
emitted by insects in tiny
quantities
called bombykol is emitted
by the silkworm moth to
attract other moths and has
one cis and one trans double
bond

General, Organic, and Biological Chemistry

14
Name each, using cistrans prefixes when needed.
Br Br
A. C C
H H

CH3 H
B. C C
H CH3

CH3 Cl
C. C C
H Cl
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 Br Br cis-1,2-Dibromoethene
A. C C
H H

CH3 H trans-2-Butene
B. C C
H CH3

CH3 Cl
C. C C 1,1-Dichloropropene
Identical atoms; no cis or
H Cl trans

16
Addition Reactions

17
In addition reactions,
reactants add to the carbon atoms in double or triple bonds
a double or triple bond is easily broken, which makes them
very reactive

18
19
In hydrogenation,
hydrogen atoms add to the carbon atoms of a double bond or
triple bond
a catalyst such as Pt or Ni is used to speed up the reaction

20
Adding H2 to double
bonds in vegetable
oils produces
compounds with higher melting
points
solids at room temperature, such as
margarine, soft margarine, and
shortening

21
Write an equation for the hydrogenation of 1-butene using a
platinum catalyst.

22
Write an equation for the hydrogenation of 1-butene
using a platinum catalyst.

CH2CHCH2CH3 + H2 Pt CH3CH2CH2CH3

23
Draw the condensed structural formula of the product
of each the following reactions:

Pt
CH3CHCHCH3 + H2 ?

Ni
+ H2 ?

24
Draw the condensed structural formula of the product
of each the following reactions:

Pt
CH3CHCHCH3 + H2 CH3CH2CH2CH3

Ni
+ H2

25
 In halogenation, halogen atoms add to the carbon
atoms of a double bond or triple bond.

Br Br
H2C CH2 + Br2 H2C CH2

Cl Cl

HC C CH3 + 2Cl2 HC C CH3

Cl Cl
26
When bromine (Br2) is added
to an alkane, the red color Br2
of bromine persists.

to an alkene or alkyne,
the red color of bromine Br2
disappears immediately.

27
 In hydrohalogenation, the atoms of a hydrogen halide add to the
carbon atoms of a double bond or triple bond.

H Cl
CH3 CH CH CH3 + HCl CH3 CH CH CH3

H
+ HBr

Br
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When an unsymmetrical alkene undergoes
hydrohalogenation,
the H in HX adds to the carbon in the double bond that has
the greater number of H atoms

H Cl
CH3 CH CH2 Does not form

CH3 CH CH2 + HCl

C with the most H
Cl H
CH3 CH CH2 Product that forms

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In hydration,
an acid (H+) catalyst is required
water (HOH) adds to a double bond
an H atom bonds to one C in the double CC bond
an OH bonds to the other C

H OH
H+
CH3CHCHCH3 + HOH CH3CHCHCH3

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 When hydration occurs with a double bond that has an
unequal number of H atoms,
the H atom bonds to the C in the double CC bond that has
more H
the OH bonds to the C in the double CC bond that has the
fewer H atoms
OH H

H+
CH3CHCH2 + HOH CH3CHCH2
(1H) (2H)

General, Organic, and Biological Chemistry Copyright 2010 Pearson Education, Inc.
31
Part I.

Draw the condensed structural formula of the product

of each the following addition reactions :

1. CH3CHCHCH3 + Cl2(g) ?

2. Br2(l) ?

32
Part II.

Draw the condensed structural formula of the

product of each the following reactions:

A. CH3 CH CH2 + Cl2 ?

B. CH3 CH CH CH3 + HOH ?

C. + H2 ?

33
Part III.

Draw the condensed structural formula of the product

of each the following hydration reactions:

1. CH3CH2CHCHCH2CH3 + H2O ?

CH3

2. CH3CCHCH2CH3 + H2O ?

3. + H2O ?

34
Part I.
1. CH3CHCHCH3 + Cl2(g)
Cl Cl
l l
CH3CHCHCH3

2. Br2(l)

35
Part II.

Cl Cl

A. CH3 CH CH2 + Cl2 CH3 CH CH2

H OH

B. CH3 CH CH CH3 + HOH CH3 CH CH CH3

H
C. + H2

36
Part III.

H OH

1. CH3CH2CHCHCH2CH3
CH3

2. CH3CCHCH2CH3

OH H

OH
3.

H
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Polymers of Alkenes

38
Polymers are
large, long-chain molecules
found in nature, including cellulose in plants, starches in food,
and proteins and DNA in the body
also made synthetically, such as polyethylene and polystyrene,
Teflon, and nylon
made up of small repeating units called monomers
made by reaction of small alkenes

39
 In polymerization, small repeating units called monomers join to
form a long chain polymer.

40
41
42
43
What is the starting monomer for polyethylene?

44
What is the starting monomer for polyethylene?

Ethene (ethylene), CH2CH2

45
Name the monomer used to make Teflon, and use four
monomers to draw the condensed structural formula of a
portion of a Teflon polymer.

46
Name the monomer used to make Teflon, and use four monomers
to draw the condensed structural formula of a portion of a Teflon
polymer.

F F

FCCF tetrafluoroethene (monomer)

F F F F F F F F

CCCCCCCC portion of Teflon

F F F F F F F F

47
Recycling is simplified by using codes found on plastic
items.

48
What types of plastic are indicated by each of the
following codes?

3
A. PVC

B. 5
PP

C.

49
A. 3 Polyvinyl chloride
PVC

5
B. PP Polypropylene

6
C. PS Polystyrene

50
 Butadiene Polymers
A IS A COMPOUND THAT CONTAINS TWO
CARBONCARBON DOUBLE BONDS. ANOTHER
TYPE OF ADDITION POLYMER IS BASED ON DIENES
LIKE AND ITS DERIVATIVES.

51
 Butadiene Polymers
NATURAL RUBBER IS A POLYMER OF (2-
METHYL-1,3-BUTADIENE) WHICH IS ALSO A DIENE.
MANY SYNTHETIC ELASTOMERS OR RUBBERLIKE
MATERIALS ARE POLYMERS OF ISOPRENE AND OF
BUTADIENE.

52
 Butadiene Polymers
Polymers of 1,3-butadiene and isoprene are shown
below. Unlike saturated ethylene polymers, these
polymers are unsaturated. They have double bonds in
their polymeric structures.

53
 Butadiene Polymers
One synthetic rubber (styrenebutadiene rubber,
SBR) is made from the two monomers styrene and
1,3-butadiene. This polymer is a copolymer. A
copolymer is made from two different monomers.

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 Butadiene Polymers
The presence of double bonds at intervals along the
chains of rubber and rubberlike synthetic
polymers makes vulcanization possible.

Vulcanization is the cross-linking of polymer chains

with sulfur atoms.

55
 Butadiene Polymers
The physical properties of rubber can be altered by
vulcanization.

Vulcanization increases the abrasion resistance and

the useful temperature range of the polymer.

56
 Butadiene Polymers
In the segment of vulcanized rubber shown below,
the chains of polymerized isoprene are cross-linked
by sulfursulfur bonds, giving the polymer more
strength and elasticity.

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