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SKO 3013 B O C: Asic Rganic Hemistry
SKO 3013 B O C: Asic Rganic Hemistry
SKO 3013 B O C: Asic Rganic Hemistry
NAME
NO. MATRIC
NG SENG WEI
TAY SIEW BEE
D20091035105
D20081032270
Geometric al isomer
Introduction/ eliciting ideas
Overview previous lesson Learning outcomes
Applications of ideas
Problem solving 1
Reflection/ closure
The E, Z rules
Isomerism
Geometrical Isomers
Optical Isomers
Geometrical Isomers
LEARNING OUTCOMES
At the end of this subtopic, student should be able to
Distinguish
Identify
cis-trans isomerism of a given structural formula. Use sequence rules: The E, Z designation.
What happen in molecules where is involving unrestricted rotation about carbon bonds - in other words where the carbon-carbon bonds are all single?
Organic compounds which have same molecular formula but different non-interchangable geometry due to different orientation of atoms in space.
Restricted rotation (often involving carboncarbon double bonds) Maximum overlap between the p orbital of a pi bond.
CIS-TRANS ISOMERISM
PROBLEM 1
There are two steps to determine the cis or trans structure below:
First step
--------------------
Second steps
The structure that has the equivalent substituent on the same side of the imaginary is the cis stereoisomer and the opposite side is trans stereoisomer.
--------------------
--------------------
Cis-1-chloro-1-propene
Trans-1-chloro-1-propene
The two wheels on a motorcycle show the equivalent substituent on the same side of the imaginary. The body of the motorcycle shows the C=C double bond.
Trans isomer
Unbalanced seesaw
Results from rigidity in molecules and occurs in only two classes of compound:
i.
Alkenes
ii.
Cyclic compounds
i. Alkenes
1,2 -dichloroethene
These two molecules aren't the same. The carboncarbon double bond wont rotate and would have to take the models to pieces in order to convert one
Two chlorine atoms are locked on opposite side of double bond. Known as trans isomer.
Two chlorine atoms are locked on same side of double bond. Known as cis isomer.
EXAMPLE:
Because ring dont rotate freely in space like linear chains two different possibilities exist. Cis Isomers are when two atoms are on the same side of a ring. Trans Isomers are when two atoms are on different side of a ring.
H H H H
H
H H
Cis Isomers
Trans Isomers
EXAMPLE:
CH3 H H
CH3 CH3
cis-1,2-dimethylcyclohexane
CH3
trans-1,2-dimethylcyclohexane
There must be two different groups on left and right carbon to get geometric isomer.
i)
CH3CH2 C=C
ii) H C=C
CH3
H3C
iii) H3C C=C H3C H
Cl
CH3
CH3
For these molecules above , give IUPAC name for the compounds and indicate if they are geometric isomers or neither.
ii) H C=C
CH3
Cl
CH3
2-methyl-1-butene
1-chloro-2-methylpropene
2-methyl-2-butene
H3C
Geometrical Isomerism is found in compound which have Different substituent on either side of imaginary or real planner geometry. No interconvertibility (presence of pi bond ,continuous pi bond)
BOILING POINT(C) 60 48
Table shown the melting and boiling point of cis and trans isomer of 1,2-dichloroethene
Alkyl groups attached to carbon-carbon double bond tend to push electrons away from themselves and get polar molecules. Why is the boiling point of the cis isomer higher?
The U shape of cis isomer does not pack as well as the straighter shape of the trans isomer.
The poor packing in the cis isomer means that the intermolecular forces weak and less energy is needed to melt the molecule.
S
(1) (5) I
(3)
P R
(4) H
(6)
ANSWER
(2)
Here the blue and green groups are either on the same side of the bond or the apposite side.
Geometrical isomer
Cahn-IngoldPrelog priority sequence rules
Optical isomer
When dealing with a C-X bond grouping, the priority of X is given by ....
Sequence priority Rule 1:
The higher the atomic number of an atom the higher the priority it is assigned.
e.g. for typical non-metals ZX (Z = proton/atomic number) encountered in organic compounds ...
X=
53I
> 35Br > 17Cl > 16S > 15P > 8O > 7N > 6C > 1H
PROBLEM 1
Determine the stereochemistry (E or Z ) below
First step
We assure ourselves that the carbon-carbon double bond is indeed stereogenic. We draw an imaginary line perpendicular to the carboncarbon double bond
Second steps
Now rank the atoms directly bonded to the alkene carbons on each side of the imaginary line by atomic number high to-low.
The two groups of higher priority are label as 1 whereas the other two groups with lower priority are label as 2.
Third steps
Fourth steps
In this case, we cross the double bond to connect the higher ranking groups. Thus alkene has the E stereochemistry and the systematic name of the molecule is (1E)-1bromo-2-fluoro-1propene where 1 in 1 E refer to the location of the carbon-carbon double bond.
All the four steps were same in order to determine stereochemistry (E or Z ) for the structure below.
The Z isomer
(Zusammen)
Both highest priority groups are on the same side of the double bond (includes all cis configurations of the old convention). Example:
The E isomer
(Entgegen)
Two highest priority atoms/groups are diagonally opposite each other on differentsides of the plane of the double bond system (includes all trans isomers of the old convention). Example:
Z-hep-2-ene
cis/trans 2-heptene
E-hep-2-ene
Rank the set of substituents below in order of priority according to the Cahn-Ingold-Prelog sequence rules. 1 = highest priority.
To establish priority, you look at the atoms' atomic numbers and whichever one is greater takes priority. If they are equal, then you look at the next atom that it is bonded to and compare their atomic numbers. Now, if you encounter a double bond, you count that atom twice (so C=O is counted as C,O,O).
summary
Students divide into two groups Each group choose one item below for your quizzes.
1. What is the difference between structural isomer and geometric isomer? Answers:
Structural isomerism is the same emperical formula but constructed differently and different structural formula. Geometric isomerisim is where you have different isomers due to differences arrising from cis and trans arrangements of atoms.
1,1-dibromocyclobutane
Answers:
1,1-dibromocyclobutane, is a positional isomer of C4H6Br2 and cannot exhibit geometrical isomerism because the two bromine atoms are attached to the same carbon.
Answers:
E-3-methylhex-3-ene
Z-1,2-dichlorocyclopropane (cis)
E-1,2-dichlorocyclopropane (trans)
Z/cis
E/trans
LEARNING OUTCOMES
At the end of this subtopic, students are able to
Distinguish
Identify
cis-trans isomerism of a given structural formula. Use sequence rules: The E, Z designation.
HOMEWORK
Text book
Worksheets
THE END
REFERENCES
1.
Saripah Salbiah Syed Abdul Azziz, Azmi Mohamed, Mohamad Saufi Rosmi, Nurul Aini Binti Bakar dan Mimi Marzziana Hamzah. Basic Organic Chemistry. Sultan Idris Education University. Stereoisomerism Geometric Isomerism. Retrieved on 15 March 2011 at http://www.chemguide.co.uk/basicorg/isomerism/geometric.html Organic Chemistry. Retrieved on 15 March 2011 at people.bu.edu/birubio/ch203ampmpdfs/l13.pdf Cahn-Ingold-Prelog Priority Rule. Retrieved on 16 March 2011 at http://askville.amazon.com/Cahn-Ingold-Prelog-PriorityRule/AnswerViewer.do?requestId=4776615 Organic Stereoisomerism-E/Z isomerism. Retrieved on 16 March 2011 at http://www.docbrown.info/page07/isomerism2.htm
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