chapter 06 stereochemistry.pptVIP

Two or More Chiral Carbons Enantiomer? Diastereomer? Meso? Assign (R) or (S) to each chiral carbon. Enantiomers have opposite configurations at each corresponding chiral carbon. Diastereomers have some matching, some opposite configurations. Meso compounds have internal mirror plane. Maximum number is 2n, where n = the number of chiral carbons.  Examples Fischer-Rosanoff Convention Before 1951, only relative configurations could be known. Sugars and amino acids with same relative configuration as (+)-glyceraldehyde were assigned D and same as (-)-glyceraldehyde were assigned L. With X-ray crystallography, now know absolute configurations: D is (R) and L is (S). No relationship to dextro- or levorotatory.  D and L Assignments * * * = Properties of Diastereomers Diastereomers have different physical properties: m.p., b.p. They can be separated easily. Enantiomers differ only in reaction with other chiral molecules and the direction in which polarized light is rotated. Enantiomers are difficult to separate. Resolution of Enantiomers React a racemic mixture with a chiral compound to form diastereomers, which can be separated. ChromatographicResolution of Enantiomers End of Chapter 5 Chapter 6Stereochemistry Organic Chemistry, 6th EditionL. G. Wade, Jr. Yunfeng Chen School of Chemical Engineering Pharmacy chyfch@ Chirality “Handedness”: right glove doesn’t fit the left hand. Mirror-image object is different from the original object. Stereoisomers Geometric isomers: cis-trans isomers. Enantiomers: nonsuperimposable mirror images, different molecules.  = cis-1,2-dichlorocyclopentane trans -1,2-dichlorocyclopentane Chiral Carbons Tetrahedral carbons with 4 different attached groups are chiral. Its mirror image will be a different compound (enantiomer). Mirror Planes of Symmetry If two groups are the same, carbon is achiral. (animation) A molecule with an internal mirror plane