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LecturePLUS Timberlake 1
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
LecturePLUS Timberlake 2
Alkenes
Carbon-carbon double bonds
Names end in -ene
cyclohexene
LecturePLUS Timberlake 3
Alkynes
HC≡CH ethyne(acetylene)
HC≡C-CH3 propyne
LecturePLUS Timberlake 4
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
LecturePLUS Timberlake 5
Learning Check HA3
Write the IUPAC name for each of the following
unsaturated compounds:
A. CH3CH2C≡CCH3
CH3
CH3
B. CH3C=CHCH3 C.
LecturePLUS Timberlake 6
Solutions HA3
Write the IUPAC name for each of the following
unsaturated compounds:
A. CH3CH2CH=CHCH3 2-pentyne
CH3
CH3
B. CH3C=CHCH3 C.
LecturePLUS Timberlake 7
2-methyl-2-butene 3-methylcyclopentene
Cis and Trans Isomers
Double bond is fixed
Cis/trans Isomers are possible
CH = CH CH = CH
H H
ethene LecturePLUS Timberlake
ethane 9
Products of Hydrogenation
LecturePLUS Timberlake 10
Learning Check HA4
LecturePLUS Timberlake 11
Solution HA4
Ni
CH2=CHCH2CH3 + H2
CH3CH2CH2CH3
LecturePLUS Timberlake 12
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
LecturePLUS Timberlake 13
Learning Check HA5
Write the product of the following addition
reactions:
CH3CH=CHCH3 + H2
+ Br2
LecturePLUS Timberlake 14
Solution HA5
Write the product of the following addition
reactions:
CH3CH=CHCH3 + H2 CH3CH2CH2CH3
+ Br2 Br
Br
LecturePLUS Timberlake 15
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
LecturePLUS Timberlake 16
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.
LecturePLUS Timberlake 17
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.
LecturePLUS Timberlake 18
Fats and Atheroschlerosis
CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH
↑
eicosapentaenoic acid (EPA) 20 carbon atoms
CH3CH2(CH=CHCH2)5(CH2)2COOH
LecturePLUS Timberlake 20
Atherosclerosis