ORGANIC CHEMISTRY

Dr Nam T. S. Phan
Faculty of Chemical Engineering
HCMC University of Technology
Office: room 211, B2 Building
Phone: 38647256 ext. 5681
Email: ptsnam@hcmut.edu.vn
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 Chapter 5: ALKENES
An sp2
hybridized
carbon

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 NOMENCLATURE OF ALKENES
The IUPAC name of an alkene is obtained by replacing
the “ane” ending of the corresponding alkane with “ene”

• Ethylene is an acceptable synonym for ethene in the IUPAC

system
• Propylene, isobutylene and other common names ending in
“ylene” are NOT acceptable IUPAC names
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 Determine the parent
hydrocarbon – the
longest continuous
carbon chain containing
the C=C

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Note: Alkenes can have geometric isomers

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 PREPARATION OF ALKENES
Dehydrations of alcohols
Acid

isomerization
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isomerization 7

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Eliminations of alkyl halides

Base

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Alkyne hydrogenations
Pd/CaCO3 + Pb(OAc)2 / quinoline

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 REACTIONS OF ALKENES
Additions of hydrogen halides (AE)

More stable

Markovnikov’s rule 10

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 Carbocation rearrangement

More stable

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 12
More stable
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 Stereochemistry

Racemic mixture 13

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Already has 1 asymmetric carbon

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2 asymmetric carbons are created

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Additions of hydrogen bromide (AR)

Electrophilic addition (AE)

Radical addition (AR) – only for HBr 16

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Reaction
mechanism:

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 Additions of halogens

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 Major
addition
product –
NOT a
dihalide

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 Stereochemistry

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 Stereochemistry
2 asymmetric carbons are created

Trans-2-butene Æ meso compound 22

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 Additions of water – hydration reactions
Water is too weakly acidic to allow the hydrogen to act
as an electrophile

Markovnikov’s rule

H2SO4, H3PO4…
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Reaction
mechanism:

Carbocation
rearrangement
might occur

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 Alcohols by oxymercuration-reduction

Markovnikov’s rule

No carbocation formation, no rearrangement

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Additions of borane: hydroboration-oxidation

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Regioselectivity:

Anti-Markovnikov

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Additions of hydrogen – hydrogenation

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Reaction mechanism:

Syn addition

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 Stereochemistry

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Alkene epoxidations – Anti hydroxylations

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Stereochemistry

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 Reactions of epoxides

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Stereochemistry Anti additions

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Syn hydroxylations of alkenes

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Reaction mechanism: Syn additions

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Permanganate cleavage of alkenes

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 Ozonolysis of alkenes

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In the presence of an oxidizing agent, the products
will be ketones / carboxylic acids
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 Polymerizations

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