CIS AND TRANS

WHEN TO USE CIS AND TRANS IN ORGANIC COMPOUND

PRESENTED BY:
VISITACION,HANNAH MAE A.
Geometric (cis / trans) isomerism
If alkenes have two different substituents at each end of the C=C then they can exist as stereoisomers (as geometric
isomers).
This is because there is restricted rotation of the double bond due to the pi bond which means they don't readily
interconvert.
Think about what happens in molecules where If you draw a structural formula instead of using models,
there is unrestricted rotation about carbon you have to bear in mind the possibility of this free rotation
bonds - in other words where the carbon- about single bonds.
carbon bonds are all single. The next diagram
shows two possible configurations of 1,2-
dichloroethane.

But what happens if you have a carbon-carbon double
bond - as in 1,2-dichloroethene?
These two molecules aren't the same. The carbon-
carbon double bond won't rotate and so you would
have to take the models to pieces in order to convert
one structure into the other one. That is a simple test
for isomers. If you have to take a model to pieces to
convert it into another one, then you've got isomers.
Drawing structural formula for the last pair of models
gives two possible isomers.
In one, the two chlorine atoms are locked on opposite
sides of the double bond. This is known as
the trans isomer. (trans : from latin meaning "across" -
as in transatlantic).
In the other, the two chlorine atoms are locked on the
same side of the double bond. This is know as
the cis isomer. (cis : from latin meaning "on this side")
The most likely example of geometric isomerism is but-
2-ene. In one case, the CH3 groups are on opposite
sides of the double bond, and in the other case they
are on the same side.
If we consider the general alkene unit shown below,
then the alkene can exist
as cis and trans isomers only if R1 is not equal to
R2 AND R3 is not equal to R4.
1,2-disubstituted alkenes are described as:
• cis- if the two alkyl groups, R-, are on the same
side of the C=C
• trans- if the two alkyl groups, R-, are on opposite
sides of the C=C.
•these terms are inserted into the name as prefixes.
For example,  but-2-ene, where both R = methyl :
trans-but-2-ene cis-but-2-ene
Tri- or tetrasubstituted alkenes are described as cis-
and trans- based on the relative arrangement of the
groups that form the parent hydrocarbon carbon
chain that gives the root name. In the example shown the
below, the longest carbon chain that gives the root name
is highlighted in blue: