[PPT]Alkenes and Alkynes - coercingmolecules · Web view2013/01/05 · Title Alkenes and Alkynes...
Transcript of [PPT]Alkenes and Alkynes - coercingmolecules · Web view2013/01/05 · Title Alkenes and Alkynes...
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Alkenes
PropertiesNomenclature
StabilityAddition Reactions
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Ethylene
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Electron Rich -Bond
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Elements or Degrees of Unsaturation: -Bond or Ring
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Determine the # elements of Unsaturation
C8H10Br2OC8H18 is saturatedcompound is deficient by 6 "H's"3 degrees of unsaturation
O
BrBrCH2OH
CH3
Br
Br
e.g.
OH Br
Br
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Alkene Nomenclature
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Cyclic alkenes
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Alkyl Groups with -Bonds
CH=CH2
Br
cis 1-bromo-3-vinylcyclohexane
a vinyl group CH2CH=CH2
4-allylcyclopentene
an allyl group(or ethenyl)(or 2-propenyl)
a phenyl group
3-phenyl-1-nonene
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Alkylidene GroupsDouble Bonds Fused to Rings
CH2
methylenecyclohexane
CHCH3
ethylidenecyclopentane
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Polyenes
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Name these Alkenes
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Cis and Transno rotation about -bond
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cis-trans Isomers
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E/Z System
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Establish Priority of Substituents on Each sp2
Carbon
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What’s My Name?
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(Z)-4-ethyl-5-isopropyl-4-nonene
Hi
Hi
Lo
Lo
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Priorities with Multiple Bonds
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E or Z?
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E or Z?
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Name These
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3,3-dimethyl-1,4-cyclohexadiene 2-butyl-1,5-hexadiene
(E) 1-ethylidene-2-methylcyclopentane3-allylcyclohexene
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Hydrogenation Data Helps to Determine Stability
Hhydrogenation of Alkenes
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Enthalpy Change Shows Relative Energy of Alkene
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Both cis and trans 2-Butene are Hydrogenated to Butane
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“E” is More Stable than “Z” by 2.3 KJ/mol
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Relative Stabilities of Alkenes
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The Addition Reaction
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HBr Addition
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Markovnikov’s Rule
The addition of H-X across a double bond results in the more
highly substituted alkyl halide as the major product.
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Depicting a Reaction
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Addition of HBr or HClMarkovnikov Addition
Markovnikov
Br
C CH
H
HCH3
CH3
HBr
CH3
CH3
CH
HC
CH3
CH3C
H
H
Br
C
H
not formed
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Regiochemistry Determined by Stability of Intermediate
H-BrBr
H
HBr Br H
3o carbocation
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Hyperconjugation
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Carbocation Stabilitymore highly substituted, lower energy
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3o Carbocation forms Preferentially
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What Alkenes are Needed to form Theses Alkyl Halides?
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Definitions• Regioisomers – two constitutional isomers
that could result from an addition reaction. • Regiospecific – only one regiosisomer
forms at the expense of the other.• Regioselective – both regioisomers are
formed, but one is formed in preference.
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Determine the major product:
a) HCl
b)HBr
c) 2 mol HCl
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a) HCl
b)HBr
c) 2 mol HCl
Cl
H
BrH
Cl ClHH
cis and trans
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RearrangementsCH3
CH3
HCl CH3
CH3
Cl
HH Cl
CH3
CH3
H
methide shiftCH3
CH3
Cl
32o o
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Propose a Mechanism