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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 H2C=CH-CH3 ethene (ethylene) propene (propylene) cyclohexene

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Alkynes
Carbon-carbon triple bonds Names end in -yne HCCH
HCC-CH3

ethyne(acetylene)
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 CH3CH=CHCH3 CH3CH CHCH3 1-butene 2-butene 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 B. CH3C=CHCH3 2-methyl-2-butene C. 3-methylcyclopentene
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CH3

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Cis and Trans Isomers


Double bond is fixed Cis/trans Isomers are possible
CH3 CH3 CH3 CH = CH trans
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CH = CH cis

CH3
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Hydrogenation
Adds a hydrogen atom to each carbon atom of a double bond H H
Ni HC=CH + H2 HCCH H H ethene
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H H

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
+

Cl2

H2C CH2
Br Br CH3C CCH2CH3 Br Br

CH3C CCH2CH3

+ Br2

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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
+ Br2

CH3CH2CH2CH3
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 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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