Can Tho University
College of Natural Sciences
Organic chemistry
Chapter 4
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[Link]
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❑ The double bond of an alkene consists of one bond và one bond.
❑ The bond is less strong than the bond, so it is easier to break.
Binding energy of bond
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IUPAC
Prefix indicating the amount of carbon + suffix “-ene”
(Write immediately, no spaces)
❑ For compounds containing more than one double bond, depending on
the number of double bonds, the suffix "-ene" is replaced by the suffix
“-diene”, “-triene” or “-tetraene”…
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2. NOMENCLATURE
- Common names: replace the suffix “ane” with “ylene” (less common)
- IUPAC names
• The parent chain is the longest carbon chain containing the C=C double bond.
• Number the chain so that the double bond receives the lowest possible locant.
• Naming format: substituent position + substituent name + parent chain name + position
of C=C + ene.
But-1-ene But-2-ene
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Least stable
Heat of hydrogenation
Free energy
Most stable
Reaction process
Alkenes attached more substituent groups
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=> Increasing the stability of alkenes
– Cis isomers have larger substituents on the same side => Van der Waals
interactions between substituents => less stability.
– In trans isomers, the two substituents are facing away from each other
=> more stability
Cis isomers have stereochemical interactions
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Alkene Structure melting point (C) boiling point (C)
Alkenes are insoluble in water and dissolve well in organic solvents.
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❑ Why does vegetable oil exist in liquid state at room temperature, while fat exists
in solid state?
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❑ Vegetable oils and animal fats are mixtures of triacylglycerols
(triglycerides), which are esters of glycerol and fatty acids.
❑ Fatty acids can be saturated (carbon chain without double bonds) or
unsaturated (carbon chain containing double bonds).
Saturated fatty acid
Monounsaturated fatty acids Polyunsaturated fatty acids
❑ The more double bonds exit in the molecule => the lower the melting
temperature.
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5 PREPARATION
a. Dehydrohalogenation of alkyl halides (strong base/alcohol, heating)
b. Dehydration of alcohols (acid, heating)
(The major product follows Zaitsev’s rule (see the halide/alcohol derivatives chapter)
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c. Dehalogenation of vicinal dihalides (Zn/to)
C C + Zn C C + ZnX2
X X
d. Reduction of alkynes
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Complete the reactions
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Electrophilic addition reaction
Hydrohalogenation
Hydration
Halogenation
Halohydrin formation
Hydroboration-oxidation
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Electrophilic addition reaction
Main product
Markovnikov rule: in the electrophilic addition reaction of HX alkenes:
➢ The X atom added to carbon carries more substituents.
➢ The H atom added to carbon carries fewer substituents.
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Electrophilic addition reaction
The main product follows the Markovnikov rule.
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Electrophilic addition reaction
❑ The halogenation reaction is used to determine the presence of an
alkene functional group in a molecule.
❑ Reagent Br2/CCl4 uses to identify alkenes through the loss of the
characteristic red-brown color of Br2 solution.
BrBr2/CCl
2/CCl 4 mấtcolor
4 loses
màu quickly
nhanh chóng
when
Does notchứa
Không contain alkenes
alkene
khi tác dụng
reacting withvới alkene
alkenes
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Electrophilic addition reaction
❑ The reaction has Anti Markovnikov Addition Reaction (OH added to
the carbon contains fewer substituents).
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Oxidation reaction
❑ Oxidation reagent: KMnO4 and OsO4.
Cold
With alkene, the purple
KMnO4 purple color does not change. color disappears, brown-
The solution does not contain alkenes black solid MnO2 appears
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Oxidation reaction
❑ Depending on the structure of the alkene, different products will be
formed:
– The carbon of an alkene with the structure RCH= will form a carboxylate
salt.
– The carbon of an alkene with the structure R2C= will form a ketone.
– The carbon of an alkene with the structure CH2= will form CO2.
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Oxidation reaction
Ozonolysis of alkene
❑ Depending on the agent used in step 2:
– Using CH3SCH3 or Zn/CH3COOH → aldehyde/ketone.
– Using H2O2 → ketone/carboxylic acid.
– Using NaBH4 → alcohol.
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Reduction reaction
Syn addition of hydrogen to a
double bond
Easy to react Difficult to react
Alkanes have more substituent groups
Decreasing the possibility of hydrogenation reaction
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Polymerization
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Polymerization
❑ Polyethylene (PE)
❑ Polypropylene (PP)
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Polymerization
❑ Polystyrene (PS)
❑ Poly(vinyl chloride) (PVC)
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Polymerization
❑ Teflon
❑ Poly(methyl methacrylate) (PMMA)
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❑ Teflon
❑ Poly(methyl methacrylate) (PMMA)
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