Chapter 6 presentation version.ppt

Chiral compounds lack a plane of symmetry achiral

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shortcut to thinking about symmetry. Chiral compounds lack a plane of symmetry Achiral compounds possess a plane of symmetry achiral achiral chiral
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Chapter 6 - Stereochemisty Frances Oldham Kelsey 1914-2015 Thalidomide Why You Care
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Carvone - Different Smells Caraway seed spearmint
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A Chiral Compound is Optically Active If it rotates the plane clockwise = ( + ) If it rotates the place counterclockwise = ( ) A chiral compound rotates the plane of polarization of plane-polarized light .
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How to Draw Enantiomers Wedge and Dash Fischer projections are just another way of showing a tetrahedral center Fischer projections
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Naming Enantiomers Assign relative priorities to the four groups. 1 = highest priority; 4 = lowest priority
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Naming Enantiomers Identify chiral carbon, assign priorities 1 and 4 first. Evaluate connections for assigning priorities 2 and 3. 1 = highest priority 4 = lowest priority Prioritize Groups
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clockwise = R counterclockwise = S and Naming Enantiomers
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if the lowest priority group is on a hatched wedge, then clockwise = R counterclockwise = S and Naming Enantiomers draw an arrow from 1 to 2 to 3
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Swapping two groups (but only two groups) will give the opposite enatiomer. Sometimes it is easier to draw the R enantiomer and convert to S. Naming Enantiomers (S) (R)
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R and S Versus (+) and (–) Some R enantiomers are ( + ) and some are ( ).
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