Molecule
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Mirror Image
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Notes
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R-Bromochlorofluoromethane |
S-Bromochlorofluoromethane |
Probably the simplest
possible example: 4 different atoms connected to carbon.
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Spacefilling model
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Ball & Stick
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E-2-butene |
Z-2-butene |
Alkenes provide examples of stereochemistry that are important. It's not so much the atoms as the bond that provides the origin of steroisomers (though of course to change the configuration, we need to break and re-form bonds to one of the two atoms in the double bond).
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R-1-amino-1-phenylethane |
S-1-amino-1-phenylethane |
Another fairly simple
example: carbon has NH2, a phenyl ring, methyl, and H.
This illustrates how we may have to step out several bonds to find a point of difference between any of the groups attached to the stereocenter.
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Cyclohexanol |
Cyclohexanol |
No stereogenic
atoms! The two CH2 groups are identical.
See if you can identify an internal mirror plane of symmetry.
This compound is achiral.
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S, S-trans-Cyclohexanediol |
R, R-trans-Cyclohexanediol |
Each oxygen-bearing carbon
has 4 different substituents: H, OH, CH2, and CH(OH).
This compound is chiral.
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cis-Cyclohexanediol |
| Each oxygen-bearing carbon
has 4 different substituents: H, OH, CH2, and CH(OH).
However, because of internal symmetry, this molecule is achiral.
The mirror image is superimposable, although we must ring-flip one of
them first.
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D-alanine |
L-alanine |
A simple amino acid; the
central carbon has CO2-, NH3+, methyl, and H
attached.
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Morphine |
Unnatural Morphine |
A complex molecule;
clearly chiral. Several stereogenic atoms.
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