ORGANIC CHEMISTRY (PETRO)

ORGANIC CHEMISTRY
Dr Nam T. S. Phan
Faculty of Chemical Engineering
HCMC University of Technology
Office: room 211, B2 Building
Phone: 8647256 ext. 5681
Email:
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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


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

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Carbocation rearrangement

More stable

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More stable

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Additions of hydrogen bromide (AR)
Electrophilic addition (AE)

Radical addition (AR) – only for HBr

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Reaction
mechanism:

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Stereochemistry

Racemic mixture

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Already has 1 asymmetric carbon
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2 asymmetric carbons are created

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Additions of halogens

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Major
addition
product –
NOT a
dihalide

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Stereochemistry
2 asymmetric carbons are created

Trans-2-butene Æ meso compound

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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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