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

HC≡CH ethyne(acetylene)

HC≡C-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. CH3CH2C≡CCH3
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.

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2-methyl-2-butene 3-methylcyclopentene
 Cis and Trans Isomers
 Double bond is fixed
 Cis/trans Isomers are possible

CH3 CH3 CH3

CH = CH CH = CH

cis trans CH3

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 Hydrogenation
Adds a hydrogen atom to each carbon
atom of a double bond
H H H H
Ni
H–C=C–H + H2 H–C–C–H

H H
ethene LecturePLUS Timberlake
ethane 9
 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.

Cl Cl
H2C=CH2 +
Cl2 H2C CH2

Br Br
CH 3C CCH2CH 3 + Br2 CH3C CCH 2CH 3
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

+ Br2 Br

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 HDL-
cholesterol
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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