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ALKANES
Alkane Isomers
Constitutional Isomers
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CH3CH2CH2CH3 (butane)
CH3(CH2)2CH3 (butane)
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Physical Properties
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Conformers
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Torsional Strain
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Conformations of Butane
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Steric Strain
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Steroids
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Proteins
Lipids
Carbohydrates
Nucleic acids
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Naming Cycloalkanes
Find the parent. # of carbons in the ring.
1.
1.
2.
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Naming Cycloalkanes
Name the substituent.
2.
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Stereoisomerism
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Cyclopropane
3-membered ring must have planar structure
Symmetrical with CCC bond angles of 60
Requires that sp3 based bonds are bent (and
weakened)
All C-H bonds are eclipsed
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Cyclobutane
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Cyclopentane
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Cyclohexane ring
rapidly flips between
chair conformations at
room temp.
Two conformations of
monosubstituted
cyclohexane arent
equally stable.
The equatorial
conformer of methyl
cyclohexane is more
stable than the axial by
7.6 kJ/mol
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1,3-Diaxial Interactions
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In the cis isomer, both methyl groups are on the same face
of the ring, and compound can exist in two chair
conformations
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Trans-1,2-Dimethylcyclohexane
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Example: C6H10
Saturated is C6H14
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Organonitrogen compounds
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Naming of Alkenes
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Extended Comparison
RULE 2
If atomic numbers are the same, compare at next
connection point at same distance
Compare until something has higher atomic number
Do not combine always compare
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Stability of Alkenes
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Hyperconjugation
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General reaction
mechanism:
electrophilic addition
Attack of electrophile
(such as HBr) on bond
of alkene
Produces carbocation
and bromide ion
Carbocation is an
electrophile, reacting
with nucleophilic
bromide ion
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A transition state
should be similar to
an intermediate
that is close in
energy
Sequential states
on a reaction path
that are close in
energy are likely to
be close in
structure - G. S.
Hammond
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Carbocations undergo
structural
rearrangements
following set patterns
1,2-H and 1,2-alkyl shifts
occur
Goes to give more stable
carbocation
Can go through less
stable ions as
intermediates
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Alkenes are
commonly made by
elimination of HX from
alkyl halide
(dehydrohalogenation
)
elimination of H-OH
from an alcohol
(dehydration)
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Br2 is similar
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Electrophilic
addition of
bromine to give a
cation is followed
by cyclization to
give a bromonium
ion
This bromoniun ion
is a reactive
electrophile and
bromide ion is a
good nucleophile
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Orientation toward
stable C+ species
Aromatic rings do not
react
An Alternative to Bromine
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Oxymercuration Intermediates
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Non-Markonikov product
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Mechanism of Hydroboration
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Formation of Dichlorocarbene
Base removes
proton from
chloroform
Stabilized
carbanion remains
Unimolecular
elimination of Clgives electron
deficient species,
dichlorocarbene
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Reaction of Dichlorocarbene
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Simmons-Smith Reaction
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Heterogeneous
reaction between
phases
Addition of H-H is
syn
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Ozonolysis of Alkenes
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Cleavage of 1,2-diols
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A polymer is a very
large molecule
consisting of repeating
units of simpler
molecules, formed by
polymerization
Alkenes react with
radical catalysts to
undergo radical
polymerization
Ethylene is
polymerized to
poyethylene, for
example
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Polymerization: Propagation
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Polymerization: Termination
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Other Polymers
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Biological Reactions
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ALKYNES
Alkynes
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Naming Alkynes
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Addition of Hg(II) to
alkyne gives a vinylic
cation
Water adds and loses a
proton
A proton from aqueous
acid replaces Hg(II)
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Keto-enol Tautomerism
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Hydroboration/Oxidation of Alkynes
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Hydroboration/oxidation
converts terminal alkynes
to aldehydes because
addition of water is nonMarkovnikov
The product from the
mercury(II) catalyzed
hydration converts terminal
alkynes to methyl ketones
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