stereochemistry Flashcard

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enantiomers
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diasteromers
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diasteromers
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same
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constitutional isomers
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non-isomers
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diasteromers
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enantiomers
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same
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diasteromers
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chiral = the compound is not superimposeable on its mirror image
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achiral = superimposeable on its mirror image and has no stereocenters
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chiral = nonsuperimposeable on its mirror image
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chiral = nonsuperimposeable on its mirror image
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achiral and meso = superimposeable on its mirror image and has more than one stereocenters
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chiral = nonsuperimposeable on its mirror image
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achiral and meso = superimposeable on its mirror image and has more than one stereocenters
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achiral = superimposeable on its mirror image and has no stereocenters
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achiral = superimposeable on its mirror image and has no stereocenters
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chiral = nonsuperimposeable on its mirror image
chiral
if it is not superposable on its mirror image.
achiral
if it is superposable on its mirror image.
meso
if it is achiral and contains two or more stereocenters
enamtiomers
Stereoisomers that are non-superposable mirror images.
diasteromers
Stereoisomers that are non-superposable, but are not mirror images.
constitutional isomers
Isomers which contain atoms that differ in connectivity.
non-isomers
Compounds that do not have the same molecular formula.
superimposeable
A term that describes the ability to precisely overlap one object over another. Only identical objects
stereoisomers
Isomers which have atoms that differ only by their orientation in space. Unlike constitutional isomers, corresponding atoms exhibit the same connectivity.
isomers
Compounds that have the same molecular formula.
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the shell is chiral = = nonsuperimposeable on its mirror image
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a pencil is achiral = superimposeable on its mirror image
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gloves are chiral = nonsuperimposeable on its mirror image
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carbon with 4 substituents (tetrahedral) is chiral = nonsuperimposeabel to its mirror image
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carbon with 3 different substituents is achiral = superimposeable on its mirror image
Levorotary
indicates the counterclockwise rotation of plane-polarized light
D
The specific rotation of a compound is denoted by the symbol
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It has R configuration
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diasteromers
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32
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rotates plane-polarized light in a clockwise direction
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not chiral
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the following would have an enamtiomer
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is not meso
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The stereochemistry of the double bond makes the molecule have a chiral center
the following compound rotates plane-polarized light
enantiomeric excess =
(specific rotation of the mixture/ specific rotation of the pure enantiomer in excess) 100
Racemates
are equal molar mixtures of two enantiomers
S/ R
-/ +
R/S
If the lowest priority group is already projected back behind the plane (dotted line) or is within the plane (solid line) then trace through the other three groups beginning with the highest priority group first as above(1,2,3 trace).
If on the other hand, the lowest priority group is projected in front of the plane (solid wedge) then trace through the other three groups beginning with the highest priority group first as above(1,2,3 trace). Reverse the trace so that if the trace was clockwise indicating “R” configuration make it “S” configured. If the trace was counter clockwise indicating “S” then reverse it and make it clockwise making it “R” configured.
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achiral/chiral
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(a) S (b) S (c) R (d) S
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(a) Diastereomers (b) Diastereomers (c) Enantiomers (d) Identical (e) Enantiomers
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stereoisomers/not

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