Beruflich Dokumente
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Contents
Electrophilic addition to C=C
+ General mechanism
+ Electrophilic Addition to CarbonCarbon Multiple Bonds
+ Addition of HX
+ Addition of HOH and addition of YX
+ Addition to allene and alkyne
+ Substitution at -carbon
+ Reactions via organoborane intermediates
Terminal alkenes have the double bond at the end of the carbon chain.
Internal alkenes have at least one carbon atom bonded to each end of the
double bond.
Recall that the double bond consists of a bond and a bond. The
bond is stronger than the bond.
The carbon atom is sp2 hybridized to obtain trigonal planar geometry,
with bond angles of approximately 120.
2
sp
Hybridization
2p
3 sp2 orbitals
sp2
sp2
Hs
C
C
sp
2
Hs
px
sp2
sp2
H
C
sp2
C
H
Hs
Interesting Alkenes
Ethylene, an industrial starting material for many useful products
Interesting Alkenes
Addition Reactions
The characteristic reaction of alkenes is addition: the bond is broken
and two new bonds are formed.
No pi bond
Alkenes have exposed electrons, with the electron density of the bond
above and below the plane of the molecule.
Because alkenes are electron rich, simple alkenes do not react with
nucleophiles or bases, reagents that are themselves electron rich. Alkenes
react with electrophiles.
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Addition Reactions
Because the carbon atoms of a double bond are both trigonal
planar, the elements of X and Y can be added to them from the
same side or from opposite sides.
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Addition Reactions
Five addition reactions of cyclohexene
No pi bond
in products
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Electrophilic Addition of
Hydrohalogenation(HX) to C=C
Two bonds are broken in this reaction: the weak bond of the
alkene and the HX bond, and two new bonds are formed: one
to H and one to X.
Recall that the HX bond is polarized, with a partial positive
charge on H. Because the electrophilic H end of HX is attracted
to the electron-rich double bond, these reactions are called
electrophilic additions.
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A racemic mixture
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Biotransformation of C=C:
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Biotransformation of C=C:
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KEY CONCEPTS
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KEY CONCEPTS
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KEY CONCEPTS
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Electrophilic Addition to CC
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Electrophilic Addition to CC
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Electrophilic Addition to CC
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Problems
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Problems
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Problems
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Organic Chemistry
For USTH Students
Lecture 3:
Electrophilic substitution in
Aromatic systems
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Structure of benzene
Aromaticity-Hckels Rule:
+ A molecule must be cyclic
+ A molecule must be planar
+ A molecule must be completely conjugated
+ A molecule must satisfy Hckels rule, and contain a particular number
of electrons. An aromatic compound must contain 4n + 2 electrons (n
= 0, 1, 2, and so forth).
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Aromaticity-Hckels Rule ?
Antimalarial drug
that reduces fever
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Aromaticity-Hckels Rule ?
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1
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Mg
N
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MeOOC
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O phytyl
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O
1
chlorophyll a
phytyl =
Molecule of life
Buckminsterfullerene, C60
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Figure 18.1
Five examples
of electrophilic
aromatic
substitution
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o-toluidine
NH2
Cl2 (aq.)
Cl
CH3
Cl
bright yellow!
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Anti-inflammatory drug
KEY CONCEPTS
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KEY CONCEPTS
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KEY CONCEPTS
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KEY CONCEPTS
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Problems
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Problems
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Problems
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Problems
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Reaction of Carbocation
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