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Reactions
yielding alkenes often preferentially make certain isomers
over others. Most often, this is because a particular isomer
is more stable then another. Understanding what conditions
lead to this greater stability helps in determining what products
will be favored in a given reaction.
Cis
or Trans?
Generally, trans isomers are favored over their cis counterparts
because the bulky groups are separated from each other and
do not infringe upon the van der Waals radius of each other.
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| The
cis isomer (left) has strain from the isopropyl groups
infringing upon each other's radii. The trans isomer has
significantly less and is therefore more stable. |
Substituted
or not?
Alkenes generally prefer to be connected to highly substituted
carbons, a condition often referred to as Saytzeff's Rule.
Most likely this occurs because of increased stability
asa result of the added electron density from the alkyl groups
to the pi bond and because of the additional separation between
repulsing alkyl groups, going from sp3 hybridized to sp2 hybridized
(from 109.5o to 120o) which reduces
tension caused by steric effects.
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| The
alkene on the left is more stable then the one on the
right because it is substituted by an additional methyl
group. |
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