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Alkenes and Cycloalkenes: Alkenes Carbon - Carbon Double Bond
Alkenes and Cycloalkenes: Alkenes Carbon - Carbon Double Bond
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All six atoms are coplanar. The carbon–carbon bond is a double bond made up
of the s component and the p component.
The p orbitals of two sp2 hybridized carbons overlap to produce a p bond.
ALKENE NOMENCLATURE
The longest continuous chain that includes the double bond forms the base name
of the alkene, and the chain is numbered in the direction that gives the doubly
bonded carbons their lower numbers.
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ALKENE NOMENCLATURE
Hydroxyl groups, however, outrank the double bond. Compounds that contain
both a double bond and a hydroxyl group use the combined suffix -en + -ol to
signify that both functional groups are present.
2,3-dimethyl-2-butene
4-chloro-1-pentene
2-methyl-2-hexene
4-penten-2-ol
ALKENE NOMENCLATURE
Cycloalkenes
Isomerism
cis-2-Butene and trans-2-butene are stereoisomers, and the terms “cis” and
“trans” specify the configuration of the double bond.
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PREPARATION OF ALKENES:
ELIMINATION REACTIONS
DEHYDRATION OF ALCOHOLS
In the dehydration of alcohols, the H and OH are lost from adjacent carbons.
An acid catalyst is necessary.
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Elimination occurs in the direction that leads to the double bond between C-2
and C-3 (major product) more than between C-2 and C-1 (minor product).
Reactions that can proceed in more than one direction, but in which one
direction is preferred, are said to be regioselective.
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The reaction is carried out in the presence of a strong base, such as sodium
ethoxide (NaOCH2CH3) in ethyl alcohol as solvent.
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are all taking place at the same transition state. The carbon–hydrogen and
carbon–halogen bonds are in the process of being broken, the base is becoming
bonded to the hydrogen, a p bond is being formed, and the hybridization of
carbon is changing from sp3 to sp2.
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THE E1 MECHANISM
Typically, elimination by the E1 mechanism is observed only for tertiary and some
secondary alkyl halides, and then only when the base is weak or in low
concentration.
E1 = elimination unimolecular
1. rate-determining ionization of
the alkyl halide to a carbocation
2. deprotonation
of the carbocation
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THE E1 MECHANISM
HYDROGENATION OF ALKENES
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In many addition reactions the attacking reagent, unlike H2, is a polar molecule.
Hydrogen halides are among the simplest examples of polar substances that add to
alkenes.
The reactivity of the hydrogen halides reflects their ability to donate a proton. Hydrogen iodide
is the strongest acid of the hydrogen halides and reacts with alkenes at the fastest rate.
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REGIOSELECTIVITY:
MARKOVNIKOV’S RULE
REGIOSELECTIVITY:
MARKOVNIKOV’S RULE
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FREE-RADICAL ADDITION OF
HYDROGEN BROMIDE TO ALKENES
anti-Markovnikov addition
(peroxide effect)
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HYDROBORATION–OXIDATION OF ALKENES
HYDROBORATION
Hydroboration is a reaction in which a boron hydride, a compound of the type R2BH, adds to a carbon–
carbon bond. A new carbon–hydrogen bond and a carbon–boron bond result.
OXIDATION
Following hydroboration, the organoborane is oxidized by treatment with hydrogen peroxide in aqueous
base. This is the oxidation stage of the sequence; hydrogen peroxide is the oxidizing agent, and the
organoborane is converted to an alcohol.
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EPOXIDATION OF ALKENES
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EPOXIDATION OF ALKENES
OZONOLYSIS OF ALKENES
Ozone (O3) is the triatomic form of oxygen. It is a neutral but polar molecule that
can be represented as a hybrid of its two most stable Lewis structures.
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OZONOLYSIS
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POLYMERIZATION
PE
Ethylene Polyethylene
PP
Propene Polypropylene
PS
Styrene Polystyrene
PVC
Vinyl chloride Poly(vinyl chloride)
POLYMERIZATION
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POLYMERIZATION
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