Stereoisomerism
in Alkenes
What you need to know
• Explanation of the terms:
• stereoisomers (compounds with the same structural formula but with
a different arrangement in space)
• E/Z isomerism (an example of stereoisomerism, in terms of
restricted rotation about a double bond and the requirement for two
different groups to be attached to each carbon atom of the C=C
group)
• cis–trans isomerism (a special case of E/Z isomerism in which two
of the substituent groups attached to each carbon atom of the C=C
group are the same)
• Use of Cahn–Ingold–Prelog (CIP) priority rules to identify the E and
Z stereoisomers
• determination of possible E/Z or cis–trans stereoisomers of an
organic molecule, given its structural formula.
Structural and stereoisomerism
• Using molecular models (or computer modelling software), make
models of butane C4H10 and its isomer.
• These isomers are structural isomers – the atoms are arranged
differently.
Stereoisomers
• Now make models of dichloroethene C2H2Cl2 and its isomers. You
should get 3 isomers.
• You should have 1,1 dichloroethene, and two different versions of
1,2 dichloroethene.
1,1 dichloroethene is a structural isomer of 1,2 dichloroethene. The
two isomers of 1,2 dichloroethene are called stereoisomers – the
atoms are bonded in the same way to each other, but the
arrangement of atoms around the double bond is different.
1,2 dichloroethene has isomers because rotation of the double bond
is not possible.
1,1 dichloroethene 1,2 dichloroethene 1,2 dichloroethene
E isomer Z isomer
Activity 2 Test 1
1. Which of these alkenes shows stereoisomerism?
– H2C=CBr2
– CH3CH=CHCH3
– CH3CH=C(CH3)2
– CHBr=CHBr
– CHCl=CH2
[Link] simple rule enables us to decide if an alkene does not show
stereoisomerism?
3. Draw diagrams to show the E and Z isomers of those
alkenes that do show stereoisomerism
Stereoisomerism is shown by
CH3CH=CHCH3 CHBr=CHBr
E isomers
Z isomers
If one of the carbons has 2 identical groups (eg =CH 2) then
stereoisomerism cannot happen.
Use of the CIP rules for more complex
stereoisomers
• Make a models of the two stereoisomers of 1-bromo
2-chloro 2-iodoethene and draw the structures of them.
CIP rules
1. Compare the atomic number (Z) of the atoms directly attached to
the stereocentre (double bond); the group having the atom of higher
atomic number receives higher priority.
2. If there is a tie, we must consider the atoms at distance 2 from the
stereocentre—as a list is made for each group of the atoms bonded
to the one directly attached to the stereocentre. Each list is
arranged in order of decreasing atomic number. Then the lists are
compared atom by atom; at the earliest difference, the group
containing the atom of higher atomic number receives higher
priority.
Answer
• Priority
• 1 I
• 2 Br
• 3 Cl
• 4 H E isomer
I and Br have the higher atomic
numbers, and are on separate
carbon atoms so determine the
name.
Z isomer
Take it further
• Identify whether these compounds show stereoisomerism, and draw
diagrams to show the E and Z isomers of these compounds
– 3-chloro-oct-3-ene
– 3-methylhept-3-ene
– 2 chloro, 3 ethylhex-2-ene
They all show stereoisomerism
E stereoisomers Z stereoisomers
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