Ch_322a_5.03

Ch_322a_5.03 - trans isomers of an alkene, such as...

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Stereocenters A stereocenter is an atom at which the exchange of any two groups around the atom interconverts stereoisomers . Tetrahedral Carbons as Stereocenters A tetrahedral carbon with four different groups attached can exist in enantiomeric forms. It is a stereocenter because exchange of any two groups around the tetrahedral center interconverts stereoisomers. C W X Y Z * a stereocenter with four different groups The asterisk indicates a stereocenter.
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Example: 2-Butanol C C H OH CH 3 CH 2 CH 3 CH 3 H HO CH 2 CH 3 A B * * A and B are unique stereoisomeric forms of 2-butanol that are mirror image related. They are enantiomers . The central carbon is a stereocenter because the exchange of any two groups around that atom interconverts A and B . C H CH 3 CH 2 CH 3 A * HO exchange -CH 3 and OH B C CH 3 OH CH 2 CH 3 H * viewing perspective gives stereostructure above
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Stereocenters in Alkenes C=C Cl Cl H H cis C=C Cl H H trans Cl Since exchange of the Cl and H around a carbon interconverts the cis and trans stereoisomers, the carbons are stereocenters . a stereocenter The cis and
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Unformatted text preview: trans isomers of an alkene, such as 1,2-chloroethene, are stereoisomers . Since they are not related as enantiomers, they are diastereomers . Find the Stereocenter CH 3 CCH 2 CH 3 CH 3 H 2-methylbutane achiral CH 3 CCH 2 CH 3 Cl H 2-chlorobutane chiral CH 3 CH 2 CCH 2 CH 2 CH 3 CH 3 H 3-methylhexane chiral The Importance of Chirality in Biological Systems Chirality or handedness is common in nature. On the macroscopic level, helical seashells generally spiral like a right-handed screw and are chiral. Climbing vines wind in a specific direction. On the molecular level, most biologically important molecules are chiral. The biological activity of chiral molecules is specifically associated with a specific enantiomer. This specificity results from reaction between a chiral molecule and a chiral receptor that only accomodates one enantiomer. This enantioselectivity is a key factor in drug design ....
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Ch_322a_5.03 - trans isomers of an alkene, such as...

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