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Minggu-ke-4

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Isomerism resulting from double bonds (no
free rotation)
- Cis & Trans Isomers: diastereomer

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n different double bond - there are 2n
geometrical isomers .

2 different double bond - there are 4


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Problem ?

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E/Z isomerism
Isomerism resulting from double bonds
- Assignment CIP system analogy : Z
(together) and E (opposite)

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Isomerism of monocyclic compounds
- Although rings containing more than 3 C atoms are
not planar, for the purpose of assigning cis/trans
isomeris, they are considered planar.
ring (same as C=C) prevent rotation (use CIP
rules)

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Cis-Trans Isomerism in Cycloalkanes

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The terms cis and trans should be used to specify
stereoisomeric ring structures
Recall that constitutional isomers have atoms
connected in different order

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Practice Problem: Name?

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Conformations of Polycyclic Molecules
Decalin consists of two cyclohexane rings joined to share two carbon
atoms (the bridgehead carbons, C1 and C6) and a common bond

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Conformations of Polycyclic Molecules
Two isomeric forms of decalin: trans fused or cis fused
In cis-decalin hydrogen atoms at the bridgehead carbons
are on the same face of the rings
In trans-decalin, the bridgehead hydrogens are on opposite
faces
Both compounds can be represented using chair
cyclohexane conformations
Flips and rotations do not interconvert cis and trans

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Isomerism of Fused and Bridged rings

Cis/Trans fusion

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Cis- and trans- decalins

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Bicyclic

Cis-decalin

Trans-decalin

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Steroids

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Cholesterol

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Testosterone

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Geometric isomers on N compounds

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Geometric isomers on N compounds

Oxime and related compounds


- syn instead of cis
- anti instead of trans

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Bicyclic Compounds

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Camphor

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Morphine

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Exo- and endo-stereochemistry:

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Endo & Exo nomenclature
2-UNSUBSTITUTED BRIDGES OF UNEQUAL LENGTH

SHORTER BRIDGE SHORTER BRIDGE

LONGER ENDO LONGER EXO

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Special Case = Norcamphor
Two bridges of equal length, but one of them bears a
substituent (C=O). This C=O makes the bridge
heavier and therefore it is used as reference. The
orientation of the substituen on the 3 rd bridge is closer
to the heavier bridge Endo. The orientation of the
substituen on the 3 rd bridge is away to the heavier
bridge Exo.

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Endo & Exo nomenclature

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Tetrahedral geometry

Not possible to have cis-trans isomers!

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Geometric isomers

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