Chapter 11

Haloalkanes, Alkenes, and Alkynes

Alkenes and Alkynes
Geometric Isomers of Alkenes
Addition Reactions

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Saturated and Unsaturated

Compounds
Saturated compounds (alkanes) have
the maximum number of hydrogen
atoms attached to each carbon atom
Unsaturated compounds have fewer
hydrogen atoms attached to the carbon
chain than alkanes
Unsaturated compounds contain
double or triple bonds
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Alkenes
Carbon-carbon double bonds
Names end in -ene
H2C=CH2

ethene (ethylene)

H2C=CH-CH3

propene (propylene)
cyclohexene

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Alkynes
Carbon-carbon triple bonds
Names end in -yne
HCCH

ethyne(acetylene)

HCC-CH3

propyne

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Naming Alkenes and Alkynes

When the carbon chain has 4 or more C atoms,
number the chain to give the lowest number to
the double or triple bond.
1
2 3 4
CH2=CHCH2CH3

1-butene

CH3CH=CHCH3

2-butene

CH3CH CHCH3 2-butyne

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Learning Check HA3

Write the IUPAC name for each of the following
unsaturated compounds:
A.

CH3CH2CCCH3

CH3

CH3
B.

CH3C=CHCH3

C.
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Solutions HA3
Write the IUPAC name for each of the following
unsaturated compounds:
A.
CH3CH2CH=CHCH3
2-pentyne
CH3

CH3
B.

CH3C=CHCH3

C.

2-methyl-2-butene

3-methylcyclopentene

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Cis and Trans Isomers

Double bond is fixed
Cis/trans Isomers are possible
CH3

CH3

CH3

CH = CH
cis

CH = CH
trans
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CH3
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Hydrogenation
Adds a hydrogen atom to each carbon
atom of a double bond
H H
Ni

H H

HC=CH + H2

HCCH

H H
ethene

ethane

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Products of Hydrogenation
Adding H2 to vegetable oils produces
compounds with higher melting points
Margarines
Soft margarines
Shortenings (solid)

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Learning Check HA4

What is the product of adding H2 (Ni
catalyst) to 1-butene?

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Solution HA4
What is the product of adding H2 (Ni
catalyst) to 1-butene?
Ni
CH2=CHCH2CH3 + H2
CH3CH2CH2CH3
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Adding Halogens
Halogens also add to the double bond of an
alkene.
H2CCH2

Cl Cl
+

CH3C CCH2CH3

Cl2

H2C CH2

+ Br2

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Br Br
CH3C CCH2CH3
Br Br
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Learning Check HA5

Write the product of the following addition
reactions:
CH3CH=CHCH3 + H2
+ Br2

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Solution HA5
Write the product of the following addition
reactions:
CH3CH=CHCH3 + H2

CH3CH2CH2CH3
Br

+ Br2

Br
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Unsaturated Fatty Acids

Fatty acids in vegetable oils are omega-6 acids
(the first double bond occurs at carbon 6 counting
from the methyl group)
A common omega-6 acid is linoleic acid
CH3CH2CH2CH2CH2CH=CHCH2CH=CH(CH2)7COOH
6
linoleic acid,
a fatty acid
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Trans Fats
In vegetable oils, the unsaturated fats usually
contain cis double bonds.
During hydrogenation, some cis double bonds
are converted to trans double bonds (more
stable) causing a change in the fatty acid
structure
If a label states partially or fully
hydrogenated, the fats contain trans fatty
acids.
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Trans Fats
In the US, it is estimated that 2-4% of our total
Calories is in the form of trans fatty acid.
trans fatty acids behave like saturated fatty
acids in the body.
Several studies reported that trans fatty acids
raise LDL-cholesterol. Some studies also
report that trans fatty acid lower HDLcholesterol
The trans fatty acids controversy will continue
to be debated.
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Fats and Atheroschlerosis

Inuit people of Alaska have a high fat diet
and high blood cholesterol levels, but a
very low occurrence of atherosclerosis and
heart attacks.
Fat in the Intuit diet was primarily from fish
such as salmon, tuna and herring rather
than from land animals (as in the American
diet).
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Omega-3 Fatty Acids

Fatty acids in the fish oils are mostly the omega-3 type
(first double bond occurs at the third carbon counting
from the methyl group).
linolenic acid 18 carbon atoms
CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH

eicosapentaenoic acid (EPA) 20 carbon atoms

CH3CH2(CH=CHCH2)5(CH2)2COOH
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Atherosclerosis
Plaques of cholesterol adhere to the walls of the
blood vessels
Blood pressure rises as blood squeezes through
smaller blood vessels
Blood clots may form
Omega-3 fatty acids decrease the sticking of
blood platelets (fewer blood clots)
Omega-3 fatty acids can increase bleeding time
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Learning Check HA6

(1) Ture or (2) False
A. ____ There are more unsaturated fats in
vegetable oils.
B. ____ Vegetable oils have more omega-3 oils
than found in fish.
C. ____ Hydrogenation of oils converts some
cis-double bonds to trans- double bonds.
D. ____ Animal fats have more saturated fats.
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Solution HA6
(1) True or (2) False
A. _T__ There are more unsaturated fats in
vegetable oils.
B. _F__ Vegetable oils have more omega-3 oils
than found in fish.
C. _T__ Hydrogenation of oils converts some
cis-double bonds to trans- double bonds.
D. _T__ Animal fats have more saturated fats.
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